Charming Vacation Rentals in Pittsfield, MA

Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield. Free WiFi access is available in this lodge. A full kitchen, sofa bed and flat-screen cable TV are included in each guest room. The private bathrooms are equipped with a hairdryer and free toiletries. Guests at the Pittsfield Berkshire Mountain Lodge can relax in the hot tub. A games room is also available. Berkshire Museum is 6 minutes’ drive from the lodge. Barrington Stage Company: Mainstage is 7 minutes’ drive. Tanglewood is 11 minutes' drive from the lodge.

- "For the price and location it was amazing" - "Great stay as always! Staff was welcoming and friendly and the unit was clean and comfortable and met our expectations." - "This is our 3rd year here and we think the staff is friendly and outstanding." - "Just right for winter getaway" - "Cozy clean and comfortable" - "Exceptional Stay Quiet Comfortable and cozy!" - "Affordable. Could be cleaner." - "Bad beginning. Did not honor agreed on price."

While you're here, you can enjoy all the comforts of home and more, including an oven and a stovetop, as well as a dishwasher and free WiFi. Other amenities include laundry facilities, a freezer, towels, and an electric kettle.

- "Everything was Great" - "This place is very clean" - "Easy check in. Carmen was awesome. Close to stores, cafes and pet friendly." - "Great stay. Easy check-in. Comfortable." - "Our stay was perfect we will stay every time we come to town from now on Carmen is so friendly and accommodating such a great stay! Thank you" - "Cleanliness and comfort ranked very high here. We very much enjoyed the comfortable, large king bed and the cushy living room sofa. The unit was the size of a small apartment with large rooms having lots of windows and light including a large balcony with chairs - views of green leafy trees from some windows and town views from others (such as a parking lot etc. but expected being in downtown). It has a kitchen with all of the standard large and basic small appliances and all were clean and in working order. If you don’t want or need to cook in the kitchen, there are a couple of eateries within close walking distance with others at further walking/driving distances. During our two night mid week stay it was very quiet even though the Inn is off of a very busy local street. This property looks to be well used over many years and is kept to a relatively high standard of cleanliness and comfort. We had never used this type of remote check in/keyless service but it worked very well. At one point, I had to contact the Inn via phone and was able to speak with someone right away. I would not hesitate to stay here in the future. "

Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts. We are 10 minutes driving time to many corporations such as General Dynamics, Lenco Armored Cars, Lockheed Martin. When you have time to relax at the hotel take advantage of our fitness center, heated indoor pool and the 101 Restaurant for Breakfast or Dinner. The hotel is located centrally to many attractions in the Berkshires such as Tanglewood, Norman Rockwell, Hancock Shaker Village, Mass Moca, Clark Art Museum, Herman Melville, Jacob Pillow, Barrington Stage and the Colonial Theater. When it is time to bring home some gifts there are many antiques shops, specialty shops in every town in the Berkshires plus there is the Lee Premium Outlet to score some great deals. We look forward to your visit and until you walk through our doors, have a great day!

- "We stayed for 2 nights. Each employee we talked to, was professional and friendly..made us feel a." - "Great location, great views, clean and quiet." - "The 4 Cs: central, comfy, clean, cost-efficient" - "Perfect for my short stay and I'd happily consider staying longer." - "Overall nice it was my baby 5th birthday party which was fun and amazing thank you again" - "Great!" - "Great place to stay. Clean and accommodations were great."

Hotel in Pittsfield with a health club and a 24-hour business center
Along with an indoor pool, this hotel has a restaurant and a health club. Free WiFi in public areas and free self parking are also provided. Additionally, a bar/lounge, a 24-hour business center, and a conference center are onsite.
Holiday Inn & Suites Pittsfield-Berkshires by IHG offers 179 accommodations with coffee/tea makers and hair dryers. 32-inch flat-screen televisions come with digital channels. Refrigerators and microwaves are provided.

Guests can surf the web using the complimentary wired and wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Great " - "Stay was great overall. Room was well appointed and very clean. Especially liked the hotel location as it was walking distance to everything I needed. Only minor complaint is the parking as the attached garage is still under renovation? Would prefer having better access to my car, but the valet was easy enough. (cars are parked next door in the TD bank parking lot)" - "Garage is under renovation " - "Staff, friendly and accommodating"

22 miles from Tanglewood Musical Center in Hancock, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak provides accommodations with access to a hot tub. This property offers access to a pool table. There's a sun terrace and guests can use free Wifi and free private parking. Offering a patio and mountain views, the spacious vacation home includes 6 bedrooms, 3 living rooms, flat-screen TV, an equipped kitchen, and 6 bathrooms with a hot tub and a bath. Featuring air conditioning, this unit has a dressing room and a fireplace. The vacation home offers bed linen, towels, and laundry service. There is an on-site bar. For guests with children, the vacation home offers outdoor play equipment and a baby safety gate. Skiing, fishing, and hiking are possible within the area, and Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak offers ski storage space. Tanglewood is 23 miles from the accommodation, while Cranwell Spa & Golf Club is 23 miles from the property. Albany International Airport is 32 miles away.

- "Excellent retreat for large groups or multi-family get aways. We will return again in the future." - "Super excellent, highly recommended!!" - "The place is amazing! It gives us a very enjoyable vacation." - "We had and enjoyable and relaxing experience!" - "Beautiful, large home!" - "Thank you so much for such a nice place to stay. We had time for a nice campfire on final night."

Hotel with free parking, steps from Barrington Stage Company
Along with a bar/lounge, this smoke-free hotel has coffee/tea in a common area and a business center. Free WiFi in public areas and free self parking are also provided. Other amenities include concierge services, a 24-hour front desk, and tour/ticket assistance.
Hotel On North offers 45 air-conditioned accommodations with minibars and safes. Beds feature premium bedding. Flat-screen televisions come with premium cable channels. Bathrooms include bathtubs or showers and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks along with free local calls (restrictions may apply). Additionally, rooms include coffee/tea makers and irons/ironing boards. Housekeeping is provided daily.

- "Jimmy from the front desk was the best and extremely helpful. " - "Love how this hotel is anchoring the renaissance of North Street - and Pittsfield as a whole " - "A nice small hotel in excellent condition and close to local theatres. Excellent restaurant in facility." - "Very nice" - "Amazing! From the decor, to the staff, to the attention to detail. I became quite friendly with the front desk staff as I stayed for 6 days (was hiking in the Berkshires in early November). The bed, pillows, and chairs were all super comfortable, shower pressure was great, and the service was out of this world. Thank you to everyone!"

Berkshire Vacation Rentals: Chic Pittsfield Home With A View is located in Pittsfield, just 7.2 miles from Cranwell Spa & Golf Club and 7.3 miles from Tanglewood Musical Center. This vacation home provides air-conditioned accommodations with a patio. With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Guests can also relax in the garden. Tanglewood is 7.5 miles from the vacation home, while Norman Rockwell Museum is 13 miles away. Albany International Airport is 44 miles from the property.

Air Conditioner • Fireplace/Heating • Parking • Security/Safety • Internet • View • Pet Friendly

While you're here, you can enjoy all the comforts of home and more, including a refrigerator and a stovetop, as well as a dishwasher and free WiFi. Other amenities include laundry facilities, a freezer, towels, and kitchenware and utensils.

- "Highly recommended! Berkshire Mountain Lodge is my go-to when visiting the area. Easy check-in, clean & comfortable. I especially appreciate the full kitchen." - "Friendly staff. But no laundry detergent provided. " - "Its was great for family weekend getaway" - "Great stay" - "We love that the suites are fully equipped studio apartments. The lodge surrounded by woods, and it is very quiet. The lobby decor is beautiful, reminding us of the set of the movie, the Budapest Hotel. In addition to all this, it is very convenient to shopping and to all the outdoor fun, nature, and arts venues of Pittsfield."

Spacious Historic Home in the Berkshires! offers accommodations in Pittsfield, 7.8 miles from Tanglewood Musical Center and 8 miles from Tanglewood. Guests staying at this vacation home have access to a balcony. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 7.7 miles away. The air-conditioned vacation home consists of 5 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Norman Rockwell Museum is 13 miles from the vacation home. Albany International Airport is 45 miles from the property.

Child Friendly • Parking • Fireplace/Heating • Internet • Sports/Activities • Guest Services • Other • Accessibility • Pet Friendly • Security/Safety

Hotel in Pittsfield with a fitness center and a 24-hour front desk
This hotel features an indoor pool, a restaurant, and a fitness center. Free WiFi in public areas and free self parking are also provided. Additionally, a bar/lounge, a snack bar/deli, and dry cleaning are onsite.
Hilton Garden Inn Lenox Pittsfield offers 95 accommodations with MP3 docking stations and safes. LCD televisions are featured in guestrooms. Guests can make use of the in-room refrigerators, microwaves, and coffee/tea makers. Bathrooms include complimentary toiletries and hair dryers.

Guests can surf the web using the complimentary wired and wireless Internet access. Business-friendly amenities include complimentary weekday newspapers and phones. Housekeeping is provided daily.

- "Everyone was professional and courteous ✌️I also appreciated that there was no charge for parking, much appreciated. Other hotels in vegas and Myrtle Beach are charging customers $$$ to park!!!!! BTW. Jae restaurant was welcomed, great varieties, Everything delicious. I will be returning ⭐️⭐️⭐️⭐️" - "Clean and rooms ready on time " - "Very nice " - "Staff was very accommodating, my room was enormous and well kept. We were skiing and it was very convenient to the slopes. I was with 4 teens and they also had a great time."

Located off Route 20, this Pittsfield hotel is 3.5 miles from Lichtenstein Center for the Arts. The hotel features a hydro-massage tub and a gym as well as traditional rooms with free Wi-Fi. A microwave, refrigerator and coffee facilities are provided in all rooms. The Best Western Plus Berkshire Hills Inn & Suites has cable TV in the rooms. The Arrowhead Museum is 5.5 miles from the Best Western Plus Berkshire Hills Inn & Suites. Pittsfield Municipal Airport is 2.5 miles away.

- "Very good, would stay here again if in the area" - "Convenient location for our visit in Pittsfield." - "I usually stay at more expensive hotels, this particular best Western exceeded my expectations." - "Great comfortable stray at a great hotel & location" - "It was ideal for a 3-day weekend." - "Great location for a couple of affordable nights in the Berkshires!" - "We was happy." - "Comfortable and welcoming. Very helpful staff."

Hotel with free breakfast, near Hancock Shaker Village
A fitness center, a snack bar/deli, and a 24-hour business center are available at this smoke-free hotel. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, coffee/tea in a common area, a business center, and conference space are onsite.
Best Western Plus Berkshire Hills Inn & Suites offers 59 accommodations with safes and coffee/tea makers. Each accommodation is individually furnished and decorated. 37-inch LCD televisions come with premium digital channels. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

This Pittsfield hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The staff at this location goes above and beyond. The room was comfortable and clean. I would definitely return!" - "Bed was a little hard, that's my only complained., breakfast and coffee are the best." - "It was clean and comfortable!!" - "Everyone was very friendly from the continental breakfast staff to Jay at the front desk who worked a back-to-back shift when we got there due to the bad weather. I would definitely stay here again."

Fairbridge Inn Express Pittsfield is located in Pittsfield, 11 miles from Tanglewood and 11 miles from Cranwell Spa & Golf Club. This 3-star hotel offers free WiFi. Some units at the property feature a balcony with a city view. Free private parking and a business center are available, as well as a 24-hour front desk. Tanglewood Musical Center is 11 miles from the hotel, while Norman Rockwell Museum is 16 miles away. Albany International Airport is 48 miles from the property.

Internet • Child Friendly • Parking • Business Services • Air Conditioner • Guest Services

Motel in Pittsfield with a seasonal outdoor pool and a 24-hour front desk
A seasonal outdoor pool, a 24-hour front desk, and a picnic area are available at this smoke-free motel. Free WiFi in public areas and free self parking are also provided. Other amenities include a TV in a common area.
Berkshire Inn offers 38 air-conditioned accommodations with hair dryers and irons/ironing boards. Guests can make use of the in-room refrigerators and microwaves.

Guests can surf the web using the complimentary wireless Internet access. Flat-screen televisions come with cable channels. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "I always have a good stay here at the Berkshire inn, the staff is very accommodating and helpful, my room is very clean and comfortable." - "Everthing was up too its standards" - "Great time, super quiet and very clean ! " - "The room was quiet and very clean. The bathroom was beautifully remodeled, very modern and appealing. The bed was comfortable. I have stayed here multiple times while visiting the Berkshire, and I will continue. "

Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodations in Pittsfield. The hotel has a fitness center and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar. All rooms come with a TV with cable channels. The rooms are fitted with a private bathroom equipped with a bath or shower. For your comfort, you will find free toiletries and a hair dryer. Albany is 30 mi from hilton garden inn lenox, while Adams is 17 mi away. The nearest airport is Albany International Airport, 36 mi from Hilton Garden Inn Lenox/Pittsfield/Berkshires.

- "Excelent" - "Where I found my happiness" - "Great stay a bit over prices on the weekend" - "Great hotel; terrific location; helpful staff." - "Great service" - "Thoroughly enjoyed my stay and would definitely go back." - "Very pleasant stay - polite staff" - "We will stay here whenever we visit the Berkshires." - "I enjoyed my trip and the hotel was great!" - "Good family get away" - "Pleasant, comfortable"

Suburban motel in Pittsfield with free parking
Along with a business center, this motel has laundry facilities and a 24-hour front desk. Free WiFi in public areas and free self parking are also provided.
FairBridge Inn Express offers 45 accommodations with coffee/tea makers and complimentary weekday newspapers. Flat-screen televisions come with cable channels. Guests can make use of the in-room refrigerators and microwaves.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is provided daily.

- "Great for the price" - "Very nice hotel ,supermarket restaurant, shopping, center,walkmart clouser" - "It was a quiet beautiful stay " - "Good very good" - "Good" - "Very close to work." - "Nice and quiet and convenient " - "Convenient location easy check in" - "Clean room quick easy check in" - "Quiet " - "Friendly staff and quick checkin " - "great for the price" - "Room was good for price, loud music and reving of car late night at shop next door was frustrating but overall good stay as always"

Elegant Pittsfield Home Near Downtown and Skiing! is located in Pittsfield, just 7.9 miles from Tanglewood Musical Center and 8 miles from Tanglewood. With garden views, this accommodation features a patio. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 7.8 miles away. The air-conditioned vacation home consists of 5 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 4 bathrooms with a bath and a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Guests can relax in the garden at the property. Norman Rockwell Museum is 13 miles from the vacation home. Albany International Airport is 45 miles from the property.

Guest Services • Other • Fireplace/Heating • Security/Safety • Child Friendly • View • Internet • Sports/Activities • Parking • Accessibility

Hotel in Pittsfield with free breakfast and a 24-hour front desk
This smoke-free hotel features an indoor pool, a hot tub, and coffee/tea in a common area. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a business center, concierge services, and laundry facilities.
Change of towels is available on request.
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG offers 57 accommodations with coffee/tea makers and complimentary weekday newspapers. LCD televisions come with premium cable channels. Refrigerators and microwaves are provided.

Guests can surf the web using the complimentary wired and wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Business-friendly amenities include phones along with free local calls (restrictions may apply). Hypo-allergenic bedding, hair dryers, and change of towels can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Father and 11 year old stayed the night, friends (mom, granny and 14 year old ) stayed in another room. Service efficient, customer friendly, rooms good size, warm, clean bathroom, location close to everything, ski hill, shopping large, great restaurant right in front of inn. Cannot imagine better value for money anywhere. Even the breakfast was laid out early and quite sumptuous . Highly recommended ." - "Very good no complaints. Have been here before will come back again"

Pittsfield Home with Deck - 12 Mi to Jiminy Peak! is located in Pittsfield, just 12 miles from Tanglewood Musical Center and 12 miles from Tanglewood. This vacation home offers accommodations with a balcony. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The vacation home consists of 3 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a bath and a hair dryer. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Norman Rockwell Museum is 17 miles from the vacation home, while The Clark Art Institute is 20 miles from the property. Albany International Airport is 45 miles away.

Parking • Child Friendly • Internet • Guest Services • Fireplace/Heating • Other • Accessibility • Sports/Activities • Security/Safety

Unwind in Pittsfield at this charming corporate apartment. With AC, a washing machine, and WiFi, guests can enjoy a marvelous stay in this 1-bedroom retreat. It's easy to see why you'll be able to unwind at our place.

Bedding/Linens • Kitchen • Internet • Parking • Air Conditioner • Fireplace/Heating • Security/Safety • Tv • Laundry • Child Friendly

Lake Views and Dock Access - Pittsfield Cottage! is located in Pittsfield, just 12 miles from Tanglewood Musical Center and 12 miles from Tanglewood. This vacation home is 17 miles from Norman Rockwell Museum. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Albany International Airport is 43 miles away.

Oceanfront • Sports/Activities • View • Security/Safety • Other • Fireplace/Heating • Ocean View • Parking • Child Friendly • Internet • Accessibility • Guest Services

Greetings from John at the American House! This is the perfect getaway to destress and relax! This is an original Lincoln Logs home, nestled in two and a half acres of private woodland, with 100 feet of lake frontage. No noisy omotorboats at this end of the lake, just lots of wildlife and an occasional canoe or kayak. A hand crafted canoe is ready for your enjoyment, as well as 3 kayaks. Very private property with almost anything you may need provided down by the water, including an outdoor screen with projector and a dock for launching the canoe and kayaks. Check out the pictures!

Cabin sleeps five, with a queen bed in the master bedroom on main floor, a double log bed and a queen bed in the loft, as well as a twin rollaway in walk in closet. The bathroom is off the spacious den. There is an air conditioner in the master bedroom. Normally the cabin stays quite cool by following a few easy tips. Please help yourselves to the well stocked kitchen and linens. A brand new gas stove is in kitchen. Large TV in the den with lots of movies to watch. Two twelve by twelve foot Canopies right on the water with a stocked fire pit and hammocks nearby. Electricity, WIFI, refrigerator and rain barrel all conveniently located. Large outdoor screen with Bluetooth speaker for viewing movies or concerts also down by the water. New, a private screened gazebo right on the water with a gas firepit 100 ft from the main area (where the tent used to be).

- "Our stay was amazing, clean and comfortable. John was an outstanding host. The house and everything we needed plus more! Would definitely recommend. Thank you John. Sincerely Lisa & Jeff" - "Although we planned to stay here to hike the AT and paddle, we ended up also biking on the local rail trail. The place was perfectly located. The nearby restaurants were great (Zucchini's & Proprietors). It was so relaxing by the water! The wild life was great, especially the bobcat. The kitchen was fully stocked and lots of extras. Great place to stay!"

In the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi. The Bousquet Ski Area is only an 8-minute drive away. The Berkshire Inn has rooms all equipped with cable TV, a microwave, and refrigerator. They are decorated in rich colors and dark cherry wood furnishings. Continental breakfast is served between June and September in the lobby. The Inn Berkshire provides copy and fax services at the 24-hour front desk. A picnic area is also available. The motel is a 3-minute drive from the Colonial Theatre, in downtown Pittsfield. The Canoe Meadows Wildlife Sanctuary is 2 miles away and Jiminy Peak Mountain Resort is 13 miles away.

- "Everything good always stay here"

This home has been 100% remodeled! With a beautiful spot directly on Lake Pontoosuc, the new kitchen, bathrooms, fireplace and glass enclosed family room all benefit from the idyllic scenery. There's a view from every room! The home has 5 bedrooms and a convertible playroom with a futon in it. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king sized beds and 1 has a queen. The master suite has an en-suite bathroom and it's own balcony overlooking the lake. There's plenty of room for 14-15 guests. There are 2 flat screen TV's, a fireplace, a gas stove and many other upgrades and extras.

- "Our family had a wonderful stay at the home. It's in a great location, the proximity to the water was a plus, and we enjoyed hanging out in the very spacious common area. We also loved that there was almost like a separate wing/area for each set of bedrooms. It worked out really well for our group. Would definitely stay again!" - "Our large family had the most wonderful vacation in this lake front property. it is everything pictured and more. The host was readily available if needed. The home was spotless and spacious with a large open kitchen and brand new appliances. Every bed was comfortable. The lake was just a few steps from the deck and our family loved using the kayaks. The views of sunrise and sunset were spectacular. There is a bike trail nearby as well as shopping, miniature golf, theatres ,concert venues at Tanglewood and more. We left with many happy memories and we are ever grateful to Rhonda Greenberg for sharing this family home."

Your Gateway to Relaxation and Adventure in the Heart of the Berkshires Discover the perfect home base for your next getaway at our brand-new hotel, nestled in the scenic Berkshires of Western Massachusetts. Whether you're here for a peaceful weekend escape, a family adventure, or a couples retreat, we offer everything you need to rest, recharge, and explore. Start Your Day Right: Every morning begins with our complimentary Express Start™ breakfast, featuring hot options, fresh fruit, and grab-and-go choices—perfect fuel before a day of exploring. Leisure-Focused Amenities: Heated Indoor Pool – Open daily for a refreshing dip or family splash time. Fitness Center – Stay active with cardio equipment and weights. EV Charging Stations – Convenient for eco-conscious road trippers. Pet-Friendly Rooms – Bring your four-legged family members along. Complimentary Parking – No stress, no extra fees. Explore the Berkshires: Step outside and you're just minutes from the region’s top attractions: Hiking trails with stunning mountain views Tanglewood and live music venues Norman Rockwell Museum, Hancock Shaker Village, and more Charming small towns, art galleries, and farm-to-table dining The Perfect Berkshires Base: Whether you're here for leaf-peeping, skiing, summer concerts, or just some well-earned R&R, our central location in Pittsfield makes exploring easy and relaxing.

- "Perfect hotel experience" - "New hotel need to add tea bags. Would stay again." - "Great and highly recommended! Clean and bed is so comfortable." - "Overall it was good" - "Excellent" - "We had a wonderful stay, property was immaculate!"

Comfortable, quiet home in Pittsfield minutes from Tanglewood, Berkshire Theater Festivals and other year round attractions. Oldest one room school house in New England and listed as a U.S. National Historic Place. Built in 1825 and rebuilt 1843 after a fire. Morewood has been used continually by the community until being converted to a private residence in 1985. The home was completely renovated in 2010 with glass and tile bathroom and updates throughout the 1000 square foot interior located in the middle of an acre wooded lot on a quiet mountain road. The bedroom with a queen sized bed is on the ground floor next to the bathroom with a closet and electric heater. The ground floor has the bathroom, a fully equipped kitchen, the original blackboard, very large windows, a great room with dining table for eight, gas ceramic stove, sofa and TV/DVD and bedroom for two. The sofa can be converted to a queen size bed for guests or kids or to sleep in front the fireplace in the winter. The bedroom in the loft above the great room has twin beds, a Roku TV, closet and AC window unit. The wooded lot is fenced in for pet safety with a pond and running brook on two sides. The stone patio has a dining table and chairs for four, charcoal grill, Adirondack chairs and hammock under the trees near the fire pit. For background on the Berkshires watch the HGTV video on
this website about the history of Morewood School and also the Prime Video "Melville in Love" with many scenes of the Morewood estate and Herman Melville's nearby home where he wrote the great American novel "Moby Dick".

Keywords: house, berkshire, pet, friendly, schoolhouse, historic

- "We had a great stay at this former schoolhouse. Couldn’t have been more charming!" - "My wife attended 1st, 2ed, & 3rd grade at the Morewood schoolhouse back in the late 40s. It brought back so many memories for her." - "Our family was scattered for Thanksgiving this year, and our kitchen was damaged in a mishap caused by our upstairs neighbors, so we decided to escape to the Berkshires for a quiet and peaceful holiday. The lovely, big kitchen was a particular draw for us--very well stocked with quality appliances, pots and pans, and everything you might need. There's a great wine store just down the street (Spirited) and a lovely market (Guido's) as well. And while we were content on this trip to just hang out at the house, there is so much to do just a short drive away."

Located in Pittsfield and within 8.2 miles of Cranwell Spa & Golf Club, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property. The property is around 8.3 miles from Tanglewood Musical Center, 8.4 miles from Tanglewood and 13 miles from Norman Rockwell Museum. The property provides room service, an ATM and luggage storage for guests. At the hotel, each room includes a closet. Hotel on North has certain accommodations that have a safety deposit box, and rooms have a private bathroom and a desk. You can play table tennis at the accommodation. Free private parking and a business center are available, as well as a 24-hour front desk. Albany International Airport is 45 miles from the property.

- "Hotel on North is a terrific find" - "We visit this hotel a few times per year, and it will continue to be our first choice in the future." - "Friendly reception Unusual" - "We’d definitely recommend to visiting family and friends." - "Second visit. Consistent quality" - "A very unique and beautiful hotel with lovely personal touches to the decor."

Beautiful lake front house on 1.7 wooded acres on a very quiet end of Onota Lake. A long driveway takes you to this lovely 5 bedroom home equipped with all modern conveniences and comfort. A large lawn rolls to the lake which is on two sides of the house. There are two docks and small beach. Canoe, kayak, fish, and swim right from our docks and beach during the day and spend your evenings at local theater or Tanglewood. If you are out enjoying all the Berkshires have to offer during the day, this is a tranquil property to come back to at the end of the day. You will come home to a glimmering lake perfect for a sunset paddle. The barbecue and fire pit await.

The house is in the middle of the Berkshires and just three miles from the city center yet feels more like a house in the woods. You will not be on top of your neighbors here. The property is wooded, offers privacy, quiet, and some space to stretch out. The darkness and quiet of the location offer you a fine night of sleep and starry skies.
With two canoes, 5 kayaks and a stand-up paddleboard - everyone can choose their own fun whether it’s paddling around the lake, fishing, or drifting along on a floaty in the quiet coves with a good book in hand. There is a playset, lawn games and fire pit when you want to stay ashore. Board games, cable TV, and DVD’s are inside.
The kitchen is well-stocked with all appliances and pots/pans, utensils, etc. Thanksgiving dinners are no problem in this kitchen. There is a fireplace in the living room. The dining room seats 10 comfortably and looks out on and across the lake. There are two bedrooms downstairs; one with two twin beds and the other with three bunks. Upstairs there are three bedrooms, one with a king bed and two with queen beds. One of the queen bedrooms has an outdoor balcony and the king room has a sun porch with nice views of the lake. . Down by lake there is a screened in boat house with chairs to relax in.

- "The property is wonderful. First off there is a LARGE lawn, 2 canoes and at least 4 kayaks (and a paddle board) including one 2 person. The lake is really scenic and big and NOT swarming with motor boats like other lakes in the area. The water in clean and clear. Quiet neighbors and not too close to each other. There's also a dock on the property where some of us went fishing. There's a small sandy entrance to the lake right on the property which was wonderful for the little ones.House is very roomy, modern in appliances and the "look" and also very. comfortable, with lots of nice and thoughtful touches. Tons of DVDs, books, modern TV and very good streaming options. There is even a den with lots of kids' toys, books and another TV .Owner went above and beyond in many ways, including having first aid- bandages and topical meds. THere's a nice little playground on the lawn and a high quality grill also, that we used a fair bit. Every bedroom has a modern a/c unit. The beds are very comfortable and there's tons of towels etc. Good sized fridge. Big Y is just a few minutes away and a there's a nice variety of take in restaurants close by. The town itself is close by and on rainy days we found lots to do. Shaker village is very interesting to see and there's a multiplex small cinema that is very comfortable and shows the latest films for those rainy days. Owner was very accessible and always answered promptly. Also gave us other seasonal suggestions. Try it, you'll like it!"

Located in Pittsfield, within 9.2 miles of Tanglewood Musical Center and 9.4 miles of Tanglewood, Heart of the Berkshires Motel provides accommodations with a shared lounge and free WiFi as well as free private parking for guests who drive. The property has a shared kitchen and a concierge service for guests. Guest rooms are equipped with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a shower, free toiletries and a desk. Rooms are complete with a private bathroom equipped with a hairdryer, while certain rooms at the motel also offer a seating area. Guest rooms include a closet. Guests at Heart of the Berkshires Motel will be able to enjoy activities in and around Pittsfield, like fishing. Cranwell Spa & Golf Club is 9.4 miles from the accommodation, while Norman Rockwell Museum is 14 miles away. Albany International Airport is 42 miles from the property.

- "Friendly and helpful staff." - "Thumbs up. Would recommend" - "A great place to stay for weekend trips" - "Comfy, Cost-effective Stay in the Berkshires" - "It was fine for our trip." - "Clean hotel and accommodating staff" - "We would stay here again" - "Good price point if all you need is a bed and a decent bathroom" - "It was ok and convenient" - "Nice place to stay" - "Sweet little getaway" - "I was happy to have a room close to my reunion venue, even though the price was higher that was offe"

Lakefront Home for Rent. Amazing location right on the water. In the summer the whole family can swim, kayak, paddleboard or lounge on the lawn, play games, and enjoy meals on any one of the three decks. Close to skiing, hiking, restaurants, Tanglewood and everything the Berkshires have to offer. 4 bedrooms and an additional finished sleeping area in lower level and 4 full bathrooms provide enough space for everyone. Large open layout with two living areas overlooking the lake. Amazing master bedroom with a wall of windows and amazing views, balcony. Three decks to enjoy the views and a patio with a fire pit to enjoy. Jiminy peak ski resort 20 minutes away, Tanglewood 20 min, Berkshire Museum 10 minutes, and of course the lake, dock, and kayaks right outside your back door.

- "Beautiful home right on the lake. Perfect for our family. Host was friendly and responsive. Definitely recommend!!!" - "Coffee & breakfast on deck, swimming, floating, kayaking and boating (Berkshires u drive accross lake) all day, dinner on deck, fire pit and s'mores in evening and puzzles at night, who can ask for more" - "We had a wonderful time and loved the house! We will definitely be back!" - "Listing is accurate and property is spacious and comfortable. We were 3 generations and all enjoyed our stay. Kayaking was added bonus. Andrey was quick to respond to any questions. Would stay again."

Offering suites with a deck or patio, this hotel is located in the heart of the Pittsfield city center, walking distance from numerous shops and restaurants. The Berkshire Museum is 1148 feet away. A kitchen equipped with full-sized appliances is included in each suite at Berkshire Yankee Suites - An Extended Stay Hotel. Air-conditioned suites also come with a flat-screen TV and separate bedroom. Private bathrooms are provided. Wi-Fi access is provided free of charge at Berkshire Yankee Suites - An Extended Stay Hotel. Guests can also take advantage of the hotel’s luggage storage services. Country Club of the Berkshires is just 3 minutes’ drive from Berkshire Yankee Suites - An Extended Stay Hotel. Bates Memorial State Park is 5.3 mi from the hotel.

- "Will book again" - "Very satisfied :))" - "Great location, clean and all the amenities you need"

For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a bath, as well as basement game room with wet bar, pool table and shuffleboard table.

For 2019, we are excited to have finished a Brand new 1700 Sq Ft Pavered Patio with lounge chairs and a Gas Fire Pit, including a covered area under the deck to enjoy the occasional rainy days, plus stone steps going down to the water for ease of access to the lake. outdoor couch and lounge chairs for maximum relaxation.

5 Kayaks(one being a double!) & 2 Stand up paddleboards available lakeside for your use!

This 5 bedroom, 3 1/2 bath country home sits on beautiful Pontoosuc Lake. This lakefront property features a deep water dock for your boat. There is a public boat launch within 2 minutes of the house. The location is ideal for water sports, kayaking, fishing, or just enjoying the serenity of the lake. Boat rentals are available just across the lake.

Main floor:
Spacious living room, half bath, kitchen, dining area that overlooks the lake and a sprawling sunroom with a 12 foot slider off the deck. 2 outdoor tables sit 12.

The second floor has 5 bedrooms:
1. King Bed
2. King Bed
3. queen size bed
4. two twin bunk beds (sleeps four)
5. queen over queen bunk bed (sleeps four)

Bedrooms sleep 14

House has a brand new kitchen with stainless steel appliances and gas range, new second floor washer/dryer and is fully stocked with linens, towels, dishes, glassware, cooking utensils for use by guests. Outdoor gas grill

Rentals: 1 Week Min during summer period (friday to friday)

Pontoosuc Lake, is truly in the "Heart of the Berkshires" and is minutes away from local area attractions/museums/theaters:

Tanglewood
Norman Rockwell Museum
Shaker Village
Mass MOCA
Barrington Stage
Shakespeare & Company
Berkshire Playhouse
The colonial Theatre
Jacobs Pillow
Chesterwood
Clark Art Institute

Golf- several clubs within a short distance

less than 5 mins to Berkshire Mall/Target/Walmart

During the winter months it is a very short drive to skiing Jiminy Peak or Bousquet Mountain - both under a 10 min drive.

2 1/2 hr drive from NYC or Boston

- "Spectacular in every way! The pictures don’t show all so it was a very pleasant surprise to learn just how much space this house offered the 10 of us gather together (both dining room and deck tables sat 10) or to spread apart. We spent our days at the lake, kayaking, fishing and swimming. (There were plenty of kayaks and SUPs.) At night we gathered in the finished basement for a shuffleboard tournament, at the large fire pit on the patio, or played games upstairs. While there's an abundance of outdoor seating areas on the deck and patio, we are glad to have brought our own camp chairs to use lakeside as there is no seating there. (Not a complaint, just a tip for anyone planning to stay.) The only area we think that could be improved upon is to add an umbrella for some shade on the deck so it can be enjoyed during the day. This house was very clean and well-appointed and Raphael was very responsive to any questions we had, both pre-visit and during. We will go back!"

On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been attended to from stainless steel appliances, to en-suite bathrooms with king sized beds to a 70" TV in the huge family room overlooking the lake. Perfect for family gatherings, reunions, girlfriend weekends and more.

- "We had a perfect week at 126 Ridge Ave. The house was ideally set up for our reunion of five couples. The bedrooms were lovely, the kitchen large and well equipped, the common area well suited for gathering. All was clean, up-to-date, and well maintained. We especially appreciated the large dining tables inside and out for group gatherings, and the deck furniture for lounging and enjoying sunrises and sunsets over the lake. The pool was immaculate, and we enjoyed the kayaks, hammock, ping pong, and board games. Despite the large size of our gathering, there was plentiful space for socializing or withdrawing for a quiet moments when needed. Thoughtful touches such as folding camp chairs for Tanglewood concerts were delightful. The wine fridge was an unexpected bonus. Best of all, this home is ideally located for exploring Berkshire arts and culture - from MassMoca to Tanglewood to Hancock Shaker Village, Jacob's Pillow, and numerous museums. We highly recommend this lovely home."

7 MINUTES TO BOUSQUET MOUNTAIN
This charming, newly remodeled Colonial home, nestled in the heart of the Berkshires, is perfect for your next family retreat! Explore top attractions, including museums, Tanglewood, theaters, hiking, skiing, golf, shopping, and dining. Featuring central AC, four bedrooms, three gorgeous baths, a generous bonus room, brand-new appliances & a large deck overlooking a private backyard. Enjoy the serenity of nature while being minutes from life in town!

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

This home is located at the end of a cul de sac in a quiet residential neighborhood, offering the perfect balance of seclusion and convenience. Enjoy the tranquility of a country setting while being just a 10-15 minute drive from the vibrant downtowns of Lenox and Pittsfield.

Guests will have private access to the entire property.

This spacious Colonial home, nestled in a quiet neighborhood, is ideal for family getaways.

The large, modern kitchen is equipped with state-of-the-art appliances and everything needed to enjoy meals at home. Choose between the sunlit breakfast nook or the formal dining room, which comfortably seats eight. The cozy family room invites relaxation with its large sectional, TV, and wood-burning fireplace, while books and games on the shelves ensure entertainment on rainy days.

At the front of the home, the formal living room is bathed in natural light through numerous windows. Just off the family room, the sunroom is perfect for sipping your morning coffee. A convenient half-bath is also located on the first floor.

Upstairs, the master suite features a king bed, ensuite bathroom with a luxurious marble shower, soaking tub, and a small desk for an office space. Three additional bedrooms offer ample sleeping arrangements with a king bed, queen bed, and two twin beds, along with a full guest bathroom on the second floor.

The bonus room above the garage provides a larger office space and additional fold-out sofas for guests, with stairs leading down to the laundry room for added convenience.

Outside, the home opens up to a private 2-acre wooded backyard. The swing set is a delight for younger guests, while the deck is perfect for barbecues and outdoor dining.

In under 30 minutes, you can reach Jiminy Peak, Bousquet, or Butternut Mountains for skiing and winter fun. Cross-country skiing, ice skating, ice fishing, and more await nearby. Enjoy culture and entertainment just minutes away, with The Colonial Theatre, Barrington Stage Co the Berkshire Museum, shopping, and fantastic restaurants all within reach. Tanglewood is just 10 minutes away for an unforgettable experience.

Having a car will greatly enhance your ability to explore the Berkshires effectively.

LOCATION: This home is located at the end of a cul de sac in a quiet residential neighborhood, offering the perfect balance of seclusion and convenience. Enjoy the tranquility of a country setting while being just a 10-15 minute drive from the vibrant downtowns of Lenox and Pittsfield.
PETS: A dog may be allowed with owner approval. Reach out with info about your pet prior to booking including size, age, breed, and overall temperament. A $100 pet fee will be incurred upon pet approval and booking. No multiples.
PARKING:
*Home has central air conditioning.
*2 acres of woods behind the home.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

- "This is the second time I have rented this house and it has been a great experience both times. It is just as, or better than, as "advertised" on VRBO. The kitchen is extremely well-equipped. The only tiny request would be to have paper or plastic cups in the upstairs bathrooms for we pill-takers, so we do not have to risk breakage of the kitchen glasses. Thank you so much!! Sarah" - "Perfect stay for a ski week with two families. Loved all the games and books available. Plenty of room!"

In the center of Lanesborough lies a cozy 2-bedroom house that provides a peaceful escape for your upcoming trip. Imagine yourself relaxing in the soothing hot tub, soaking in the stunning views and the fresh mountain air. Indulge in the convenience of high-speed WiFi and a smart TV, perfect for cozy movie nights. Refresh your wardrobe with the in-unit washer and dryer, and start your day with a freshly brewed cup of coffee from the fully stocked kitchen. Venture out and explore the nearby Jiminy Peak Mountain Resort, Tanglewood Music Center, and Hancock Shaker Village, all within a short drive. Whether you're seeking adventure or simply a peaceful escape, this vacation home offers the perfect blend of comfort and convenience to make your stay truly unforgettable.

- "Everything was perfect. The house was neat, clean and with all the amenities we needed. We enjoyed our stay and wish we could have stayed longer and would hope to come back again." - "The house was spotless and beautifully decorated; well stocked w anything you might need during a vacation; easy access to markets, cultural sites, recreation options plus a covered porch w comfy chairs; and a hot tub! The hosts are readily available, welcoming, friendly, caring and professional. When in the area, this would be a happy and risk/stress free VRBO choice."

2 minutes to Bartlett's Apple Orchard, Richmond
5 minutes to Bousquet Ski Area, Pittsfield
6 minutes to Balderdash Cellars- Pittsfield
6 minutes to Hancock Shaker Village - Pittsfield
9 minutes to Barrington Stage Company- downtown Pittsfield
10 minutes to Tanglewood - Lenox
12 minutes to Pittsfield's State Forest
24 minutes to Jiminy Peak- Hancock
29 minutes to Ski Butternut- Great Barrington

WORK FROM (our) HOME
Our home office has dual monitors, a wireless keyboard, mouse, and docking station to make working remotely a breeze (more details below).

Julie and Andy have spent the last 3 years doing a complete renovation to their vacation home rental named Jandie's, to make it a clean, safe place for families and individuals to enjoy the Berkshires.

The landscape is that of a storybook. A large deck sits on the front of the house overlooking the sprawling driveway lined with crab apple trees.

Kids and adults of all ages will love spending time in this ENORMOUS yard. If the season is right, you might even be able to pick your own blueberries right in the backyard!

This open-concept home has mountain views of the west with sunsets that are breathtaking year-round. The eastern views include beautiful sunrises and water views of the Tracy Brook Wildlife Sanctuary just across the street, where there is an active Heron nesting site & beaver dam. There are also ducks, geese, fish, frogs & peepers!

If you have to spend time in the kitchen on vacation, it should be a dream. The brand-new kitchen has custom cabinetry, modern appliances & is fully equipped!
You can also enjoy grilling on the deck right off the kitchen, with views the Berkshires are known for.

The Details:
Main living area: 3 electric loveseat recliners, gas fireplace, and 55-inch smart TV

Dining: Formal dining room table that seats six and an additional high-top table that seats 4.

Guest-bedroom #1: First floor, queen bed

First-floor bath: Full bathroom with large shower.

Guest-bedroom #2: Second floor, queen bed, smart TV

Guest bedroom #3: Second floor, 2 extra long twin beds that can convert to a king & 2 twin beds.
A queen 24" air mattress is also available, making this extra-large bedroom a perfect slumber party for up to 6 kids!

Second-floor bath: Full bathroom with tub/shower combo with heat for that spa-like experience

The walk-in finished basement has a super comfortable pull out couch for sleeping privacy & is conveniently accessed by the driveway.

Office:
-(2) Side-by-side HP 24mh FHD Monitors with 23.8-Inch IPS Display (1080p) - Built-In Speakers and VESA Mounting - Height/Tilt Adjustment for Ergonomic Viewing - HDMI and DisplayPort
-Logitech MK345 Wireless Combo Full-Sized Keyboard with Palm Rest and Comfortable Right-Handed Mouse, 2.4 GHz Wireless USB Receiver, Compatible with PC, Laptop
-Docking Station, UtechSmart 12 in 1 Full Quadruple Display USB C Docking Station, USB C Hub Compatible for macOS&Windows,Thunderbolt 3 Dock(HDMI,VGA,PD3.0,USB-C,Ethernet,SD/TF Card Reader,USB Ports)

Please know that we are taking COVID-19 very seriously & taking all the necessary precautions to stop the spread.

- "Thanks so much Julie! Your home and property are so beautiful, and everything was just wonderful! The love shows, and we benefited! HJ and Bruce" - "Stayed at Jandie’s house while visiting Tanglewood summer concerts in Lenox, MA. Beautiful property, super clean, spacious, well-stocked kitchen (seriously better than my own kitchen!) and convenient location. The open layout of kitchen and dining area makes it very easy for everyone to gather around. The host, Julie, was very kind & thoughtful. Definitely one of the best VRBO experiences"

Your Berkshire Winter Getaway near Jiminy Peak ❄️⛷️

Snowy slopes, twinkling lights, and cozy nights await. This spacious 6-bed, 5.5-bath historic inn sits just 4 minutes to Jiminy Peak and minutes to Ioka Valley Farm for Christmas trees, maple syrup, and holiday cheer. After a day of skiing or exploring the Berkshires, come home to an 8-person hot tub, crackling fire pit, and plenty of room for everyone to relax.

What makes winter here special

🎿 Ski Jiminy Peak: 45 Trails and 9 Lifts are just minutes away, with winter activities for all levels, a quaint village and night skiing under the lights.

🌲 Holiday magic at Ioka Valley Farm: Cut your own Christmas tree, pick up local maple syrup, or visit the farm store for cozy treats and gifts.

🔥 Gather & unwind: Soak in the hot tub as snow falls around you, make s’mores by the fire pit, or curl up in one of several inviting lounge spaces after a day on the slopes.

Built for groups: Five unique common areas mean kids can play while adults relax. A full chef’s kitchen makes shared meals simple and memorable.

Rooms you’ll love (sleeping arrangements)

🛏️ Bedroom 1: (Queen, ensuite): Classic Ethan Allen pieces, walk-in closet, soaking tub.

🛏️ Bedroom 2: (Queen, ensuite access): Vintage clawfoot charm; adjoins Bedroom 3 for family setups.

🛏️ Bedroom 3: (Full, ensuite access): Romantic full canopy bed with attached bath.

🛏️ Bedroom 4: Bunk Room (4 Twins + Trundle, ensuite): The ultimate kid hangout with its own bathroom. Sleeps 5

🛏️ Bedroom 5: Bunk Room (2 Twins + Trundle): Flexible sleeping for cousins and friends; adjoins Bedroom 6.

🛏️ Bedroom 6: (1 Twin): Cozy corner perfect for quiet mornings and a good book.

🔑 The Suite: Optional Suite Add-On (ground level): Keypad entry with 2 Queen beds, smart TV, mini-fridge, microwave, sofa, table, and desk. Great for grandparents or anyone wanting extra privacy or space. $200 first night, then $100/night.

Five places to gather (and spread out)

🎱 Billiards & Bar Room: Pool table, 55" TV, bar area for game nights.

🎮 Game Den: Foosball, poker table, sofa bed, 55" TV! Kid-approved.

🛋️ Living Room: Plush seating, 65" smart TV, electric fireplace, antiques including an 1870s piano and grandfather clock.

🌤️ Sunroom Reading Nook: Bright and quiet with books and local guides.

🍳 Chef’s Kitchen + Dining Room: Fully equipped for family dinners; dining seats 8 comfortably with extra spots at the breakfast nook.

Outdoor spaces made for winter

💦 8-Person Hot Tub: The ultimate après-ski spot after a day on the slopes or snowshoe trails. Soak under the stars as the snow falls.

🔥 Fire Pit: Gather with cocoa or mulled wine, share stories, and stargaze by the glow of the fire.

❄️ Large Deck with Grill: Enjoy crisp mountain air, peaceful snowfall, and mountain glimpses while you cook or relax.

🌲 1-Acre Yard + Stream: A quiet, snow-covered landscape for winter walks, family photos, and fun.

Location perks for winter

⛷️ Jiminy Peak: Just 4 minutes away: ski, snowboard, or go night skiing under the lights. Lift ticket discounts available for our guests!

🌲 Ioka Valley Farm: Cut your own Christmas tree, pick up fresh maple syrup, or visit for winter treats and gifts.

🏛️ Hancock Shaker Village • Williamstown • Mount Greylock: Explore holiday markets, cozy cafés, museums, and scenic drives through snow-dusted Berkshires.

Good to know

✅ Historic charm with modern comforts.

✅ Flexible sleeping for large families and groups.

✅ First-floor sleeping available via the optional Suite.

✅ Exclusive Jiminy Peak lift ticket discounts.

✅ Whole-home heating systems and fast Wi-Fi for chilly days.

Why groups pick us

👥 Staying all together beats booking multiple hotel rooms in price and quality. Cook shared meals in the chef’s kitchen, relax in five cozy hangout spaces, unwind in the hot tub, or gather by the fire after a day on the slopes. It’s the Berkshire winter experience, done right.

Ready for your winter escape?

Plan your unforgettable ski getaway at Hancock Village Inn today! 🏔️✨

Fast Facts (FAQ)

~4 minutes (1.8 miles) to Jiminy Peak

~Sleeps up to 16+ • 6 bedrooms • 5.5 baths

~Wi-Fi speed: 328 Mbps down / 128 up

Parking: 6 on-site spaces & side driveway to provide extra space/large vehicles

Cooling: Central AC throughout entire house

Heat: Forced air

Workspaces: 2 desks

TVs: 3 smart TVs with streaming apps

Dining seats: 8 at table + 4 at island • Patio seats 10

Laundry: in-unit washer/dryer in mudroom

Accessibility: 2 steps to entry • Main-level bedroom (suite additional cost)

Rules at a Glance

Quiet hours: 10 pm–8 am • Registered guests only • No parties

Hot tub (8-person): shower before use; no glass; please close cover after

Pets: not allowed

Security: System and exterior cameras • No interior cameras

No smoking indoors

Check-In / Check-Out

Keyless entry. Code sent the morning of arrival. Activates after 4:00 pm.

Check-out by 10 am.

Good to Know

1-acre yard • Fire pit • Grill • Game/billiards room • Stream across the road

Coffee: drip maker and Keurig

Winter: driveway snow service 2 inches; salt and shovels provided. Hancock/Jiminy roads are well maintained

Nearby: Ioka Valley Farm 3 min • Hancock Shaker Village 19 min • Williamstown & The Clark 15 min • Mount Greylock 12 min

- "The hosts were excellent communicators and kept in touch throughout the stay and were super helpful. Property was as described and so close to jimny peak. If we return to the mountain we would book this house agai ." - "Had a great time in Hancock. The property was clean, comfortable, and fully equipped. Kids loved the pool table, the badminton, and the foosball. Beautiful setting ideally located for our music festival at MassMoca. Some great sightseeing nearby, including Mt Greylock and Hancock Shaker Village."

Brand new construction directly on Lake Pontoosuc. This home sleeps 14 guests. There is a brand new chef’s kitchen! There are spectacular lake views from wherever you stand. A family room as well as an extra den/game room area. The house offers a side deck with a BBQ that gets sun all day long. There is also a shaded patio are in the back. But the icing on the cake is the bird’s nest on the top floor that looks out over the entire lake and has a outdoor fireplace. It is a really special spot. This home is available for renting Sunday to Sunday during the summer months.

- "Our vacation was peaceful. This home has many amenities including kayaks! The lak" - "This house was wonderful!!! Everyone loved it and raved about it! Plenty of space, and bathrooms for everyone! The house was clean and had stunning views of the lake! We really enjoyed the house and made great memories together. " - "House is beautiful! Lake views amazing! We had 3 family’s for a ski weekend at Jiminey peak, " - "Beautiful views. Main floor had an open floor plan allowing us to all be together comfortably; some watching TV, others conversing at the dining room table while a couple us were in the kitchen making dinner. Each bedroom was spacious with comfortable beds. This was a great place for our family and friends who flew across the country for my daughters college graduation from Williams College."

7 MINUTES TO BOUSQUET MOUNTAIN
Escape with family & friends to this hidden oasis in the heart of the Berkshires.

Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

The property is at the top of the hill overlooking October Mountain. You will need AWD/4WD in the winter to ascend the street and driveway. The views are gorgeous and the location is just perfect. All Berkshire attractions are easy to get to from this spot.

Guests will have private access to the entire home, and property.

A lovely colonial at the end of a quiet cul de sac with central air conditioning for summer nights & all the fixings to get warm & cozy after a day on the slopes.

The main floor of this home includes a fully equipped kitchen with a viking range perfect for cooking meals at home. A small dining area in the kitchen seats 4 guests with the formal dining room seating an additional 8 guests. The family room features gorgeous mountain views, plenty of comfortable seating, large TV and sound system. and a wood burning fireplace. Enjoy your morning coffee in the light filled screened in porch off of the family room.

An additional sitting room houses a wood stove and a collection of board games. It is adjacent to the music room which contains a beautiful piano and additional seating. The French doors off of this room lead into the library that houses some of the extensive book collection in the home. The library also doubles as the first floor bedroom with a queen sized bed. Also on the first floor is a full bath with a walk in shower and washer/dryer unit.

The second floor of this home contains the other four bedrooms. The primary bedroom and ensuite bathroom contains a king sized bed, TV, walk in closet, and a desk perfect for a private work space. The second and third bedrooms both feature queen sized beds. The final bedroom includes two twin XL beds both with twin trundle beds, accommodating up to four guests. An additional full guest bath with a tub/shower combo is located on this floor.

The basement of this home features a home gym, bar, pool table, and ping pong table. A tv area with kids games/play area is also located in the lower level.

The outside of this home is just as stunning and spacious as the inside. With beautiful mountain views and perennial gardens in the front and an expansive backyard with a fire pit, hot tub, outdoor dining table and BBQ you have everything you need right at home!

This property is a true gem, offering something for everyone. Hiking, skiing, shopping, theater, golf, lakes, nature preserves, museums, & amazing restaurants all close by.

The house is a short drive to both downtown Lenox (7 mins) and downtown Pittsfield (9 mins). A car is recommended to get around but biking is also an option, especially in warmer seasons. Downtown Pittsfield's Joseph Scelsi Intermodal Transportation Center has a bus station (Peter Pan, Bonanza, Greyhound, BRTA) and an Amtrak train station that provide regular service throughout the region and to major cities.

Look no further; this is your ideal home away from home!

Having a car will greatly enhance your ability to explore the Berkshires effectively.

LOCATION: The property is at the top of the hill overlooking October Mountain. You will need AWD/4WD in the winter to ascend the street and driveway. The views are gorgeous and the location is just perfect. All Berkshire attractions are easy to get to from this spot.
PETS: Small, trained, hypoallergenic pets are allowed on a case by case basis and for an additional $100 fee per pet. We have allergies in our family and do not, under any circumstances, allow pets that shed (even in the case of a service animal). Any pets must be under 50 lbs and fully housebroken/trained. If you'd like you to bring your pet, please let us know so we can ensure they are safe at our unique property.
PARKING: Free parking on premises.
HOT TUB: Please keep the hot tub closed when not in use. Make sure the jets are off before you close up. Be aware of the potential health risks associated with hot tubs before you use it, and use at your own risk.
*Please note that the fire pit may not be cleared in winter months due to heavy snows. Shovels will be available in the event that the fire pit is buried!

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

- "This was a great place to stay for a family group, a bunch of friends, several couples. It wasnt good for us because we are too old to deal with all the steps. The house is on top of a hilly street, with a beautiful view to October Mountain, and is landscaped to perfection, and has a whole bunch of recreational features and cozy sitting areas, but there are steps to enter the house, steps to get to the deck, steps to the very nice bedrooms, steps to throw out the trash, etc. We recommend this house without reservation, as long as you are ok with stairs!"

Relax in your island cottage overlooking beautiful Onota Lake in the heart of the Berkshires. Take in 180 degree pristine lake and mountain views from the cozy living room. Custom kitchen with everything you need. Peaceful and spacious queen bedroom. Comfortable living room has full size sofa bed to accommodate whole families. Convenient lake access with beach and boat launch just a few houses away to launch your very own kayak or canoe. Beautiful deck, patio and gardens offer lots of outdoor space to unwind. Cottage is completely updated with open floor plan, stylish details and fully equipped for short- and long-term getaways. Central AC, WIFI, and gas heating for year-round comfort.

- "Took my son to go fishing, Magnet fishing. He played with his remote control speed boat. We grilled out and enjoyed the beautiful view.." - "the place is amazing and the owners are so responsive and nice; views are spectacular and such a comfortable place to kick back and relax. very special place. we loved our stay there so very much." - "We had a great time. House was beautiful and very clean, in a lovely neighborhood!"

My name is Christine and next to my home is a lovely summer cottage. The cottage has two bedrooms, full kitchen and bath and a screened in porch. It is full of great energy and is a peaceful retreat. You can spend your evenings on the porch in your Adirondack chairs watching fireflies and reveling in the silence. This charming cottage is for those who want a total escape. It was built in the late 1800’s and is located on a quiet street in Lanesborough within walking distance to the lake. It is completely furnished with everything you need.

As soon as you enter, you will feel at home in this lovely Summer cottage. It is available June through mid-September. Included is a window air conditioner in the bedroom and a floor AC unit in the living room. There is a space heater and electric blanket for our chilly Berkshire mornings. The second bedroom has a double bed.

There is access to the lake (bring your kayak!!), lots of country for walking and hiking. Short drive to Mass MoCA, Tanglewood, and all other Berkshire amenities.

The owner is close by and available for any questions you have. Flat screen TV in living room with several streaming channels (Netflix, Peacock, CBS, YouTube, Roku, etc)

Below is a sample of over 100 reviews received on another "similar" short-term rental site:

"Christine’s little cottage is nothing short of magical! The second we walked into the space we felt a sense of happiness. It’s a small space, but the way it is laid out truly made the best use of the space and it never felt crowded. The cottage itself was in a very convenient location in relation to local attractions and amenities. As someone with celiac disease it was an absolute thrill to find Biggins Diggins just down the street, and Krispy Cone was a super fun ice cream treat for the kiddo! The main purpose of our trip was to check out the Jiminy Peak Mountain Adventure Park, which was a short 15-minute drive away and was a blast! All in all, this was one of the best experiences I’ve ever had with an A----- we hope to be back sooner rather than later!"

PLEASE NOTE THAT THIS IS STRICTLY A SUMMER COTTAGE AS THERE IS NO HEAT OR INSULATION. Thank you!

- "We stayed here after Tanglewood and it was perdect! The cottage was very homey and nicely decorated and the front porch was great for morning coffee. Christine wa a great communicator. Would definitely stay again " - "A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! " - "Adorable old cabin! We were so comfortable and thoroughly enjoyed the screened in porch! Host was kind and attentive. We had roses, cookies, and an anniversary message on the table. We would love to come back!"

Large 2nd floor fully furnished apartment in 2 story corner house with plenty of parking and separate back entrance/staircase. Eat in Kitchen with all new appliances including a washer and dryer. Freshly refinished hardwoods throughout and new kitchen vinyl planking. All new furniture and bedding including area rugs. An additional bonus room that can be used as a sitting room or study. Plenty of closet and storage space. Large covered porch off the living room. Downtown Pittsfield Is 2 miles. Close to lakes and 5 minutes from Bousquet ski area.

- "Easy to deal with the landlord. Great location" - "A homey, informal no frills but well equipped and maintained home away from home. Safe and secure, conveniently located. Julie is available and quickly responsive to questions and requests. We were very happy with our choice to be her guests." - "Great host, great communication. Comfortable accommodations." - "Great spot! Thanks, Julie!" - "I cannot say enough good things about my stay. Julie was a terrific hostess. Pittsfield is such an inviting area."

New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort , 20 minutes from Jiminy Peak, and minutes from hiking and museums.
Tanglewood in Lenox only 15 minutes away. Hang out on the deck, play yard games and cook out on the grill with friends and family.

- "It was a convenient location for visiting Tanglewood and the kitchen is perfect for packing picnics. Lovely neighborhood too!" - "We were SO happy with our stay! The house is absolutely adorable, situated on a quiet dead end street with a big yard/deck, and communication with the host was seamless. The house is nicely decorated, is outftted with anything you could ever need (even games which our kids loved!), and was IMMACULATE. Beds were super comfy too. We frequent the Berkshires often and look forward to staying here again!"

Motel in Pittsfield
Laundry facilities and free WiFi in public areas are available at this motel.
Housekeeping is available on request.
Heart of the Berkshires offers 17 air-conditioned accommodations with coffee/tea makers and hair dryers. Each accommodation is individually decorated. Beds feature premium bedding. 32-inch Smart televisions come with digital channels.

Bathrooms include showers and complimentary toiletries. Guests can surf the web using the complimentary wireless Internet access (speed: 500+ Mbps (good for 6+ people or 10+ devices)). Housekeeping is provided on request.

- "Was great comfy quiet "

The Berkshire Mountain Lodge features one-bedroom condominiums equipped with modern amenities such as full kitchens and cozy living and dining areas. The Berkshires is a cultural art haven that is home to attractions like American author Edith Wharton’s self-designed estate, The Mount and Tanglewood, the summer home of the Boston Symphony. Located near Lenox, Mass Berkshire Mountain Lodge is a family vacation destination for all seasons that will include days filled with countryside beauty, and an abundance of activities that stimulate the senses and energize the body. During the summer and spring visit the area’s many museums, theaters, concert halls, and historic homes. The county’s lakes and rivers are perfect for boating, kayaking, swimming, and fishing. Take advantage of the miles of country lanes for hiking and biking, enjoy a round of golf or go zip-lining with the kids on a nearby mountain. Many places pale in comparison to the Berkshires fall foliage season. A refuge of natural beauty; experience nature’s kaleidoscope of colors in cooler weather while you peruse though numerous outdoor bazaars and markets.

- "We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"

Welcome to this adorable apartment in Pittsfield. This cozy space features 1 bedroom with a comfortable queen bed, a fully equipped bathroom with a hairdryer and shower, and convenient amenities like WiFi and AC. Our place will help you feel at home while you're traveling in Pittsfield.

Bedding/Linens • Fireplace/Heating • Balcony/Terrace • Air Conditioner • Child Friendly • Security/Safety • Kitchen • Other • Entertainment • Sports/Activities • Pool • Laundry

1 Bedroom, 1 bath with 1 off-street parking space. Cozy renovated unit features western and eastern exposures, eat in kitchen, stainless steel appliances,microwave, dishwasher, granite countertops, bathroom with bathtub and window, finished partial wood floors, mini splits throughout apt. and private porch. Property is conveniently located nearby to hospitals, restaurants, shops, transportation hubs, parks, lakes, gas stations, financial institutions, Skiing facilities, shops, grocery stores,car wash, restaurants, laundry and dry cleaning services.

Security/Safety • Other • Air Conditioner • Kitchen • Internet • Child Friendly

Berkshire Mountain Lodge is a family vacation destination for all seasons. Surrounded by beautiful countryside, historical museums, fine dining and lots of shopping! With newly renovated 1 bedroom- 1 bath suites. There are limited availability for pets with dogs less than 35 pounds and we must verify pet friendly availability at time of reservation. On-site property includes a large indoor heated pool, business center, concierge services & fitness center. There are gas grills & outside hot tub, arcade. Nearby activities include bicycling, cross country skiing, downhill skiing, fishing, driving range for golf, miniature golf, hiking, horseback riding, ping pong, lake, ski school, & snowboard lessons. There are multiple restaurants close by with a grocery store across the street. Bousquet Mountain Ski Resort is 2 minute drive. Jimmy Peak Mountain Resort is 30 minute drive. Downtown is less than 3 miles from the Lodge. The closest airport is Albany International Airport (ALB) and approximately 1 hour drive to the Lodge. The Lodge has the following fees at the time of check in: Amenities fee of $20;credit card only. Mandatory security deposit fee $150 (refundable if no damages). Housekeeping fee of $40. There is no timeshare presentation required, as you are considered my guest when on-site. This lodge is Vape and Smoke free. This is more of large hotel suites or small condo stay. Elevators to access rooms.

General Information about the area:

Area Guide
Local Attractions:
Arrowhead Museum – 2.3 miles / 5 minutes driving
Baker’s Golf Center – 9.9 miles / 18 minutes driving
Barrington Stage Company – 3.3 miles / 8 minutes driving
Berkshire Scenic Railway – offers 1-hour, 10 mile round trip train ride from Historic Adams station
Berkshire Museum – 2.8 miles / 6 minutes driving
Bousquet Mountain – 0.7 miles / 1 minute driving
Catamount Adventure Park – 29.7 miles / 36 minutes driving
Crab Apple White Water Rafting – 37.5 miles / 1 hour driving
Hancock Shaker Village (Historic Sites) – 4.9 miles away / 10 minutes driving
Jiminy Peak Adventure Park – 26 minutes / 20.3 miles driving
Lee Premium Outlets – 9.4 miles / 16 minutes driving
Lenox, MA – 4.1 miles away / 7 minutes driving
Mt. Greylock / Appalachian Trail (Hiking) – 19.6 miles / 35 minutes driving
Norman Rockwell Museum – 10.4 miles away / 18 minutes driving
Onota Boat Livery – 8.3 miles away / 14 minutes driving
Peter W. Foote Vietnam Veterans Memorial Skating Rink – 25.5 miles / 48 minutes driving
Tanglewood Music Festival – 11.1 miles / 16 minutes driving
The Range (Family Recreation Center) – 24.9 miles / 41 minutes driving

The scenic hills, trails, lakes and rivers of the Berkshires beckon those who enjoy an active lifestyle. Biking and hiking, running and riding and skiing and skating are just a sampling of the exhilarating sporting activities that this region offers its visitors year round. There’s also tennis, swimming, fishing and even a world-class spa.

The Berkshires offer those who like to shop a veritable feast of shopping experiences. From the charming stores of its small towns to traditional malls and outlet centers, you’ll find just what you’re looking for and more. Dining is an experience unto its own in the Berkshires where some of the most enjoyable culinary treats can be found in the charming cottages, restored mills, and antiquated farmhouses that dot this legendary territory.

Wellness Facilities • Tv • Balcony/Terrace • Kitchen • Pool • Laundry • Internet • Security/Safety • Accessibility • Other • Air Conditioner • Parking

Enjoy a stylish, all inclusive experience at this centrally-located apartment. Located in downtown Pittsfield, Ma. A quiet, spacious two bedroom apartment designed with the travel worker in mind. Whether you are a travel nurse, travel doctor, travel for theater or travel for fun we have designed our spaces for your comfort. We are located minutes from the hospital with off street parking. WiFi, smart TVs, massage chair, comfy beds and a fully stocked kitchen , just bring is yourself.

Tv • Parking • Security/Safety • Air Conditioner • Laundry • Kitchen • Internet • Child Friendly • Other • Bedding/Linens • Fireplace/Heating • Wellness Facilities

Experience Pittsfield like a local in this 2-bedroom house. The bedrooms feature 2 queen beds, perfect for a tremendous night's sleep. This soothing property includes amenities like AC, WiFi, and a washing machine. Enjoy the excellent bathroom amenities, including a hair dryer. Relax in this excellent space with incredible view of beautiful Pontoosuc Lake and make the most of your stay in Pittsfield. Enjoy all that Pittsfield has to offer when you stay at our place. Located close to Jiminy Peak, Ramblewild, Tangelwood, Rusty Anchor Marinia & Pub.

Fireplace/Heating • Other • Internet • Security/Safety • Balcony/Terrace • Parking • Wellness Facilities • Air Conditioner • Bedding/Linens • Laundry • Tv • Kitchen