Best Accommodations in Berkshire

This bed and breakfast in the scenic Berkshires features uniquely styled guest rooms, each with a private bathroom. Hiking and bicycle trails in Kennedy Park are just 1 mile away. Rooms at the The Dewey by The Lenox Collection feature free Wi-Fi access and a seating area. They are decorated in bright colors, wood floors, and plush bedding. Select rooms have a fireplace or a TV. Guests can relax on the large terrace or in the library at the The Dewey by The Lenox Collection B&B. Conceirge services and daily newspapers are also available. Continental breakfast with local, in-season produce is served every morning. Tanglewood Musical Center is 5 minutes’ drive from the inn. Edith Wharton’s Estate, The Mount, is 2 miles away.

- "This brief getaway has been relaxing and most enjoyable." - "Just what you would imagine a New England Inn would offer." - "Lovely room, comfortable and quiet," - "good room but a negative regarding lack of staff and no coffee maker in room" - "Fabulous location but not good value for money overall" - "Part of the experience of old inn is the charm and a component to the charm is usually the staff. I was surprised at th"

Adults-only beach bed & breakfast
A snack bar/deli, a picnic area, and free breakfast are available at this smoke-free bed & breakfast. Free WiFi in public areas and free self parking are also provided.
Lakehouse Inn offers 14 air-conditioned accommodations with complimentary toiletries. Flat-screen televisions come with premium cable channels.

Bathrooms include showers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is offered daily and irons/ironing boards can be requested.

- "Gorgeous location and the staff were amazing. " - "There are so many nice things to say about this place, you'll have to go there for yourself and find out!! " - "I had the most amazing breakfast here. The staff provides a list of great local restaurants, trails, and activities to do for visitors. The property is located in a beautiful spot and they provided kayaks and paddle boards for guests to use, which were a huge plus to our stay. Will definitely stay here again when we visit Southern Berkshires area!"

Brook Farm Inn enjoys a location in Lenox, 1.7 miles from Tanglewood Musical Center and 1.8 miles from Tanglewood. Featuring a seasonal outdoor swimming pool, the 4-star bed and breakfast has air-conditioned rooms with free Wifi, each with a private bathroom. There's private parking and the property features an electric vehicle charging station. Every unit comes with a wardrobe and a flat-screen TV, and some units at the bed and breakfast have a balcony. At the bed and breakfast, the units are equipped with bed linen and towels. À la carte and full English/Irish breakfast options with warm dishes, pancakes, and fruit are available. Guests can also warm up near the outdoor fireplace after a day of skiing. Cranwell Spa & Golf Club is 1.9 miles from the bed and breakfast, while Norman Rockwell Museum is 6.7 miles from the property. Albany International Airport is 49 miles away.

- "Lovely visit, enjoyed every second." - "We loved it. It was very relaxing and enjoyable. A perfect quick get away to the beautiful Berkshires" - "An oasis of peace, tranquility and gracious hosts at Brook Farm Inn" - "A great inn in the Berkshires, would definitely recommend" - "Loved it! Quaint and comfy stay!" - "Wonderful! Hope to return!" - "Romantic getaway!" - "Charming location and room!" - "Delightful"

Bed & breakfast in Lee with free breakfast and a 24-hour front desk
This bed & breakfast features an outdoor pool, a business center, and a meeting room. Free full breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Additionally, concierge services, a 24-hour front desk, and a library are onsite.
Devonfield Inn B&B offers 11 air-conditioned accommodations with complimentary newspapers and complimentary bottled water. Accommodations offer separate sitting areas. Beds feature premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathtubs or showers with jetted bathtubs, bathrobes, complimentary toiletries, and hair dryers. This Lee bed & breakfast provides complimentary wired and wireless Internet access. Housekeeping is provided daily.

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

- "The classic character of the Inn is so beautiful and adds to the whole experience!" - "It was a great last minute trip. The property is very well maintained and decorated for the holidays. I wish Doug and Tim a great holiday season and Happy New Year. We will be back!!" - "A really amazing property tucked away in a hidden gem of a town. The house itself is just amazing, a very cozy stay. Our bed was the most comfortable and calming with a faint aroma of strawberries everytime I turned over. I can’t wait to go back."

Located in Lenox, 1.5 miles from Tanglewood Musical Center, Doctor Sax House has accommodations with a shared lounge, free private parking, a terrace and a restaurant. With a bar, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The property provides a concierge service and luggage storage space for guests. At the hotel, the rooms have a closet. All rooms in Doctor Sax House are equipped with a coffee machine and an iPad. Speaking English and Spanish at the 24-hour front desk, staff are willing to help at any time of the day. Cranwell Spa & Golf Club is 1.5 miles from the accommodation, while Tanglewood is 1.6 miles from the property. Albany International Airport is 48 miles away.

- "A Gem in the Heart of the Berkshires" - "Enjoyed our stay but would check out the bathroom next time." - "Lovely spot, ideal location."

Bed & breakfast in Lee with free breakfast and a 24-hour fitness center
An outdoor pool, a 24-hour fitness center, and spa services are available at this smoke-free bed & breakfast. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a microwave in a common area, a refrigerator in a common area, and a seasonal outdoor pool are onsite.
The Inn at Stockbridge offers 14 air-conditioned accommodations with designer toiletries and hair dryers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels.

This Lee bed & breakfast provides complimentary wired and wireless Internet access. Additionally, rooms include irons/ironing boards and complimentary toiletries. Housekeeping is provided daily.

- "Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 " - "Fantastic!" - "Well-run and elegant property. " - "We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"

Devonfield Inn in Lee provides accommodations with a garden, a terrace, and a shared lounge. Featuring a seasonal outdoor swimming pool, the 4-star bed and breakfast has air-conditioned rooms with free Wifi, each with a private bathroom. The accommodation features a shared kitchen, luggage storage space, and organizing tours for guests. At the bed and breakfast, each unit has a flat-screen TV with cable channels. Guests at the bed and breakfast will be able to enjoy activities in and around Lee, like fishing and hiking. Skiing and cycling can be enjoyed nearby, while a ski pass sales point and ski storage space are also available on-site. Cranwell Spa & Golf Club is 3.8 miles from Devonfield Inn, while Norman Rockwell Museum is 5.7 miles from the property. Bradley International Airport is 50 miles away.

- "DOUG and JIM will make you feel at home right away. They will make you feel comfortable about traveling the area and giv" - "A fantastic experience ... everything you would want a B&B to be"

Adults-only bed & breakfast in Lenox with free breakfast
Along with coffee/tea in a common area, this smoke-free bed & breakfast has express check-in and express check-out. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a lobby fireplace.
33 Main offers 8 air-conditioned accommodations with bathrobes and hair dryers. Each accommodation is individually decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include showers and complimentary toiletries. Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Additionally, rooms include irons/ironing boards and portable fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

- "33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! " - "Clean room, gracious host." - "Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. " - "Love this!" - "I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"

Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute. The vacation home, set in a building dating from 1900, is 3.5 miles from Tanglewood Musical Center and 3.6 miles from Tanglewood. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 3.3 miles away. Opening onto a balcony, the air-conditioned vacation home consists of 2 bedrooms. Providing a terrace, this vacation home also offers a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. The accommodation is non-smoking. Guests at the vacation home will be able to enjoy activities in and around Lenox, like skiing and cycling. Great Falls is 28 miles from Restored 1881 Farm House, while Canaan Village Historic District is 28 miles away. Albany International Airport is 48 miles from the property.

Balcony/Terrace • Barbecue/Outdoor Cooking • Internet • Child Friendly • Security/Safety • Sports/Activities • Other • Pet Friendly • Skiing • Air Conditioner • Fireplace/Heating

Bed & breakfast with free parking, near Lee Premium Outlets
A snack bar/deli, a hot tub, and spa services are available at this smoke-free bed & breakfast. Free WiFi in public areas and free self parking are also provided. Additionally, express check-in, express check-out, and free newspapers are onsite.
Chambery Inn offers 9 air-conditioned accommodations with iPod docking stations and MP3 docking stations. Each accommodation is individually furnished and decorated. 50-inch Smart televisions come with cable channels and Netflix. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

This Lee bed & breakfast provides complimentary wireless Internet access. Business-friendly amenities include complimentary newspapers and phones; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include espresso makers and coffee/tea makers. Housekeeping is provided daily.

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

- "Fantastic inn, great location, service above and beyond.. we left a sweater behind and received a call immediately letting us know!" - "Beautiful New England style room- with all of the necessities close by. This was a great layover stop for us on our way to the ocean. The hostess, Julie, was pleasant and helpful. You can’t go wrong here. We will be back to explore this area again and request our room again as well. 😊" - "Amazing place.."

Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods is located in Becket, just 17 miles from Tanglewood Musical Center and 17 miles from Tanglewood. The air-conditioned accommodation is 14 miles from Cranwell Spa & Golf Club. Norman Rockwell Museum is 18 miles from the vacation home. With free Wifi, this 2-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Bradley International Airport is 41 miles from the property.

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

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a TV, as well as a garden and air conditioning. Other amenities include premium bedding, towels, a picnic area, and a phone.

- "Hosts were super friendly and thoughtful. Rooms were neat and clean and our bathroom had just been beautifully renovated. Breakfasts were absolutely delicious and far beyond what we expected! Close, easy walk to restaurants and downtown as well as hiking trails. Highly recommend and we'll certainly be back!" - "Our stay at The Dewey was fantastic! Everything was easy and efficient, and it was so close to both town and Tanglewood. The bed was comfortable, the water pressure in the 3rd floor shower was fantastic, and the room was well-appointed without being overly crowded. I also have to commend the owners for their attention to detail - after many, many years of traveling all over the world, this was the first time I have ever stayed in a hotel where the hairdryer came with a diffuser attachment. (What a treat for my curls!) We would definitely stay here again."

Berkshire Vacation Rentals: Stonebridge Cabin: Modern Amenities Enjoy Nature is located in Lee, just 6.7 miles from Cranwell Spa & Golf Club and 9.2 miles from Tanglewood Musical Center. This vacation home provides air-conditioned accommodations with a patio. Haystack Mountain State Park is 26 miles from the vacation home and Great Falls is 27 miles away. With free Wifi, this 4-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood is 9.3 miles from the vacation home, while Norman Rockwell Museum is 10 miles from the property. Bradley International Airport is 51 miles away.

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

Adults-only bed & breakfast with free breakfast and a seasonal outdoor pool
Along with an outdoor pool, this smoke-free bed & breakfast has a bar/lounge and a poolside bar. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a seasonal outdoor pool, conference space, and concierge services are onsite.
Housekeeping is available once per stay.
Brook Farm Inn offers 15 air-conditioned accommodations with complimentary toiletries and ceiling fans. Beds feature premium bedding. Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Irons/ironing boards and change of towels can be requested. Rollaway/extra beds (surcharge) are also available. Housekeeping is provided once per stay.
Recreational amenities at the bed & breakfast include an outdoor pool.

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

- "We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time! " - "We had a wonderful stay, with the owners going out of their way to accommodate us and making sure we were having a good trip, finding places to eat, and so on. The Inn itself is lovely and quiet -- we had a ground floor room and could not hear a thing from the main sitting room just on the other side of our door -- and breakfast was excellent."

Urban Peak Escape offers accommodations in Lenox, 1.7 miles from Tanglewood Musical Center and 1.8 miles from Tanglewood. This apartment features air-conditioned accommodations with a balcony. Private parking can be arranged at an extra charge. With free Wifi, this 2-bedroom apartment offers a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the apartment. The accommodation is non-smoking. Cranwell Spa & Golf Club is 1.8 miles from the apartment, while Norman Rockwell Museum is 6.8 miles from the property.

Guest Services • Child Friendly • Air Conditioner • Other • Security/Safety • Internet • Parking

Lakefront condo resort with a fitness center and a sauna
This smoke-free condo resort features an indoor pool, an outdoor pool, and a fitness center. Free WiFi in public areas and free self parking are also provided. Additionally, a sauna, a hot tub, and an outdoor tennis court are onsite.
Each condo boasts a fireplace and offers free WiFi and a kitchen. For a bit of entertainment, a TV comes with cable channels, and guests can also appreciate conveniences like a refrigerator and a microwave. Housekeeping is not available.
The Ponds at Foxhollow offers 48 air-conditioned accommodations with fireplaces and coffee/tea makers. Rooms open to balconies or patios. Accommodations at this 3-star condominium resort have kitchens with refrigerators, microwaves, cookware/dishes/utensils, and dishwashers. Bathrooms include bathtubs or showers, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Televisions come with cable channels.

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

- "It was quiet and peaceful with beautiful scenery" - "Spacious, well equiped" - "We had to find a place last minute and we really lucked out. Beautiful environment, very spacious rooms and comfortable at that. Very nicely priced as well. Would definitely stay here again and longer next time." - "Driving distance from Teo's! :) Professional and welcoming staff! :) The Ponds at Foxhollow would be a great experience for artists, historians, and storytellers and early risers like me. I appreciated the safe environment to get up and get out for a walk in the fresh air, stepping through the morning dew in the grass along the road. Surrounded by trees, birds, and other harmless wildlife, I walked down the drive and stumbled upon Foxhollow Manor, impressed by its symmetry while pondering its history. Accompanying me back to my condo was a family of geese, two adults and seven goslings. The property was lush with open space. I remember thinking The Ponds at Foxhollow would be a perfect location for big families and large groups that might like ultimate frisbee or volleyball. We are looking forward to returning to take advantage of the pool, canoe, tennis courts, and the paddle boat. The Berkshires is rich with culture. We traveled North Adams to visit MCLA and later, from The Ponds at Foxhollow, we drove just 11 minutes south toward Stockbridge to experience the beautiful landscapes at the Botanical Gardens. I miss Tanglewood concerts! We did take advantage of having the kitchen in the spacious condo by buying breakfast food, snacks, coffee, and tea to keep "eating out" costs to a minimum. Each morning, we ate breakfast on the lanai overseeing the pond with the white marble bridge and the tiny water fountain around which the family of geese took their morning swim :)"

Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing offers accommodations in Lee, 4.8 miles from Norman Rockwell Museum and 6.4 miles from Tanglewood Musical Center. Guests may go for a swim in the private pool. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 4.8 miles away. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a kettle, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. A water park is available on-site, and both skiing and cycling can be enjoyed close to the vacation home. Tanglewood is 6.5 miles from Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing, while Great Falls is 22 miles away. Albany International Airport is 50 miles from the property.

Pool • Skiing • Sports/Activities • Barbecue/Outdoor Cooking • Security/Safety • Air Conditioner • Fireplace/Heating • Child Friendly • Internet • Other

Bed & breakfast in Lee with free breakfast
This smoke-free bed & breakfast features free breakfast, free self parking, and free WiFi in public areas.
The Red Door B&B offers 3 air-conditioned accommodations with hair dryers and complimentary toiletries. These individually decorated and furnished accommodations have separate sitting areas. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include showers. Housekeeping is offered daily and irons/ironing boards can be requested.

- "Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious." - "Lovely, lovely, lovely... thank you for receiving me." - "We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "

13 miles from Cranwell Spa & Golf Club in Otis, Private Berkshires Home On 5+ Acres Rustic & Chic features accommodations with access to a fitness center. This vacation home provides air-conditioned accommodations with a patio. Tanglewood Musical Center is 16 miles away and Tanglewood is 16 miles from the vacation home. With free Wifi, this 5-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. Norman Rockwell Museum is 16 miles from the vacation home, while Haystack Mountain State Park is 30 miles away. Bradley International Airport is 41 miles from the property.

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

After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar.

• Pools, Gym, Movie Theater and mini golf 
• Accommodate up to 6 people 
• One guest in the party, must be at least 21 y/o or older.   

* U$10 PER NIGHT OF RESORT FEE. 
**Additional charge 
The space
We offer multiple units at this property, all of them consistently designed to give you a beautiful place to stay. While the style is consistent, the layout and view may vary by apartment. 
 
• Apartment style accommodation with 823 square feet
• Queen-size bed and pullout sleeper sofa
• Fully equipped kitchen
• Two full baths
• TV in living room and bedroom
• Accommodate up to 6 people 

BEDROOM 1 - 1 Queen bed 
BEDROOM 2 - 1 Queen bed 
LIVING ROOM – 1 Pullout sleeper sofa    

• FREE PARKING
• Two Outdoors Pools (opened Seasonally), Two Indoor Pools
• Hot Tub
• Heating and air conditioning
• Towels & Linen

***** PLEASE NOTE *****
This is a Resort Villa style unit, you will have your unit assigned upon arrival, ALL units have the same quality and specification, location may vary.

***** LONG STAYS INFO: 

We do provide a starter kit for each unit with toiletries, toilet paper, paper towel, dish washer, detergent, etc. 
Guest access
You will check in at the front desk , The person whose name is on the booking must be the one that will check in, name changes only can be made up to 7 days before arrival and have a cost of $50 American dollars.
 
Check-in time: 4:00pm 
Check-out time: 10:00am 
Any late check out inquire, must be discussed direct in the property`s front desk. 
Other things to note
SECURITY DEPOSIT: Resort will require a deposit for incidentals or damages at check-in. You can use a credit or debit card, the deposit is U$115 per apartment. This is a preauthorization, not charged and released at check-out if not needed. Credit cards usually are refund in 2-3 days, while debit cards can take longer. Please contact your financial institution for more details.   

RESORT FEE: The amount of $10 + tax will be charged per night of your stay (it is not per person) this amount will cover Wi-Fi and other amenities. This amount is NOT included in your VRBO price. 
 

This is a timeshare resort, you are MY GUEST, that means you HAVE NOT to attend any timeshare presentation. 
Timeshare tour is not required but may be offered by the resort for incentives. 
WE DO NOT promote, endorse or encourage any sales pit however is up to you to accept in case it is offered, again, you are not required. 
 

PLEASE CHECK OUR CANCELATION POLICY. Always is smart to buy a travel cancelation insurance, this way you always can have full refund in case you cancel. 

**Once the reservation is confirmed, it is NOT possible to change dates and for changing names there will be a fee of €50. 
 

Rules for change of names: 

1. Name changes may be accepted up to 7 (seven) days before check-in. Note that on some special and promotional dates the name change is not accepted. 

2. Each name change has an additional rate of € 50. 

- "Comfortable and clean cottage with easy access to Lee, Stockbridge and Tanglewood"