Best Vacation Rentals in Pittsfield

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.

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

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.

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

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.

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

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

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.

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

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.

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