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Booking.com
USD 138*
View Deal
#2 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Special offer
Offers & AnnouncementsBOOK DIRECT & SAVE!
Savings alert! 19% below average rates

The price you found is 19% lower than this hotel's average rate of USD 170/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 4 days ago
Incredible Service, Perfect Stay

On a complete whim I decided to treat my GF to a one night getaway before she left for a month long trip to India. I did some quick research on areas I knew close to me, and I couldn't be more... more

Reviewed 6 days ago
Terrific weekend away

We had a very enjoyable and relaxing weekend at the Inn at Stockbridge. We stayed in the Rockwell Suite in the barn and it was very spacious and comfortable. The property is very well maintained. I... more

Contact
30 East St, Rt 7 North, Stockbridge, MA 01262-9708
+1 855-713-0473
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Fitness centre
Booking.com
USD 201*
View Deal
#3 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 3 weeks ago
Short but sweet

Bruce and his staff did an amazing job making us at home. Our room was perfect! Lovely fireplace with real wood...plenty of hot water for a nice long bath and a lovely breakfast. The property is... more

Reviewed 4 weeks ago
Romantic Birthday Getaway

For my fiancé’s birthday I wanted to treat him to a weekend of luxury. After some online research I discovered this Inn. Upon arrival, we were greeted by a subtle smell of a wood burning fireplace... more

Contact
85 Stockbridge Rd, Lee, MA 01238-9308
(413) 248-4328
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
SAVE USD 8
USD 159*
Booking.com
USD 151*
View Deal
#4 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Special offer
Special OfferSAVE 15% OFF STAY!
Reviews
Reviewed 2 weeks ago
Fall color trip to MA

We were touring MA for fall color changes. We stayed in Cornell Inn. It is a beautiful place. The owner and staff are very friendly and helpful. Breakfast was great and rooms were nicely decorated... more

Reviewed 2 weeks ago
Wonderful Weekend Winter Break

I made a last minute decision to travel with a friend to the Berkshires for the weekend. Looking for Inns in Lenox, Cornell Inn had excellent reviews and was very reasonably priced. We gave it a go... more

Contact
203 Main St, Lenox, MA 01240-2384
(413) 551-3060
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Bar/Lounge
Booking.com
USD 161*
View Deal
#5 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 2 weeks ago
Wainwright Inn is a gem!

A beautiful,historic inn in a great location. The rooms are lovely and the parlor with roaring fireplace is a treat on chilly evenings. Walking distance to Great Barrington shops and restaurants... more

Reviewed 2 weeks ago
Home away from home !

very clean, quiet, spacious . staff is very accommodating and breakfast's were delicious. we would stay there again. a good value. a very short distance from down town. we walked to town. also there... more

Contact
518 Main St, Great Barrington, MA 01230-2006
(413) 207-9472
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
SAVE USD 26
USD 168*
Booking.com
USD 142*
View Deal
#6 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 1 week ago
Absolutely delightful!

Wonderful time spent at this lovely and most welcoming inn with my daughter, celebrating her 14th birthday. I have stayed at inns all over world and I would have to say this one is now at the top... more

Reviewed 1 week ago
Looking forward to another stay!

We're frequent visitors to the Berkshires, a friend recommended we try the Federal House Inn after her recent stay - so glad we've met Marcia and Ken! Loved our very quiet and private room with... more

Contact
1560 Pleasant Street, Route 102, Lee, MA 01238
+1 855-249-1264
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Booking.com
USD 222*
View Deal
#7 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 1 week ago
Wonderful getaway!

Peaceful, relaxing and so comfortable! We spent the weekend in the Adriana Room with the comfort of a beautiful fireplace. The room was cozy, clean and welcoming! We were looking for a quiet... more

Reviewed 1 week ago
The Gateways Inn exceeded our expectations in every way imaginable!

From the moment we arrived at the inn we were like guests whose arrival was warmly anticipated by the hosts! A gilded age cottage, a phenomenal room, and entertainment in a very close and personal... more

Contact
51 Walker St, Lenox, MA 01240-2719
(413) 207-9482
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Restaurant
  • Bar/Lounge
Orbitz.com
USD 145*
View Deal
#8 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 2 weeks ago
Great Spot

Felt right at home, and was welcomed like family. When I booked the room Michele asked what I wanted to eat for breakfast. Clean, comfortable bed, coffee maker and cookies in the lobby, magazines to... more

Reviewed 2 weeks ago
A very nice return visit--after 20+ years!

We returned to Windflower after more than 20 years...we were not aware of the new ownership until we arrived and saw how nicely the grounds and interior had been spruced up. Michelle and Tom were... more

Contact
684 S Egremont Rd, Great Barrington, MA 01230-1932
(413) 650-1340
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
Booking.com
USD 223*
View Deal
#9 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 3 weeks ago
Just for us

This past weekend (1/19-1/21/18) we did a husband & wife get-a-way weekend at the Brook Farm Inn while our kids were at a camp in Pittsfield. It really felt like they were running a B&B just for us... more

Reviewed 7 January 2018
Wonderful Stay!

Warm and inviting place to stay. Everything was great! I enjoyed the room that I stayed in. The room had comfortable beds and cozy blankets to snuggle up in. Great location for a bunch of shops and... more

Contact
15 Hawthorne St, Lenox, MA 01240-2404
+1 800-285-7638
Hotel website
Amenities
  • Free Wifi
  • Free Parking
SAVE USD 12
USD 235*
Priceline
USD 223*
View Deal
#12 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 4 weeks ago
Felt like home......

The Stockbridge Country Inn is located in a beautiful, very peaceful area of Stockbridge and is only minutes away from town. The location is perfect to visit The Norman Rockwell Museum, Chesterwood... more

Reviewed 27 December 2017
Beautiful weekend get-away!

The weather didn't cooperate for us, but we still completely enjoyed our stay! The owners were really nice :) We enjoyed sitting by fireplace sipping hot chocolate. The location was perfect... more

Contact
26 Glendale Rd., PO Box 525, Stockbridge, MA 01262
(413) 207-9285
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
SAVE USD 11
USD 165*
Hotels.com
USD 154*
View Deal
#14 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 7 January 2018
An amazing midweek getaway

This place is magical. We loved the attention to detail and every little thing was thought of. We brought our dog, Bob and Mary supplied us with dog bags, a blanket and towels for our pup as well as... more

Reviewed 29 September 2017
Perfect lovely inn

Wonderful little inn with warm hospitality. Bob and Mary are great innkeepers and it's obvious that they enjoy what they do. The area is chock full of places to go and things to do and see, no matter... more

Contact
7 Albany Rd, Oak Street, West Stockbridge, MA 01266-9505
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Booking.com
USD 302*
View Deal
#15 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 2 weeks ago
Fabulous Find!

My husband and I recently spent 2 nights at the Inn to celebrate my 70th birthday. We wanted to get away, without traveling too far, and just relax, and this was the perfect place--45 min. from our... more

Reviewed 3 weeks ago
A great retreat away from it all

My wife and I had a great stay. First, the negatives, as everything else was outstanding. The bath room had a stale smell due to the old wood flooring and the impact of the water on it; it might be... more

Contact
134 Hartsville New Marlboro Rd, Rte 57, Village Green, New Marlborough, MA 01230-2159
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Bar/Lounge
Booking.com
USD 387*
View Deal
#16 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 4 weeks ago
Outstanding in Every Way

I had the great pleasure of staying at The Kemble Inn between Christmas and New Years and cannot speak highly enough of the experience. My boyfriend and I spent four days floating through this grand... more

Reviewed 11 December 2017
Great visit

Great location, great room. Service was excellent. The staff went out of their way to make our stay excellent, including having an actual wood burning fire burning upon arrival! Had no plans to... more

Contact
2 Kemble St, Lenox, MA 01240-2813
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Restaurant
  • Room Service
  • Bar/Lounge
SAVE USD 17
USD 234*
Booking.com
USD 217*
View Deal
#18 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 5 weeks ago
Another wonderful and relaxing stay and Lenox's finest B&B!

We returned for our second visit to the end over 3 years since our last visit. We were excited to meet the new owners, Tom and Debbie who took over the inn with ambition and enthusiasm! We met Tom... more

Reviewed 4 December 2017
Hospitality at Its Best in the Berkshires!

I don't write many Trip Advisor reviews any more but in this case I just had to. We had the pleasure of staying at the Birchwood Inn in Lenox MA this weekend and we found the kind of hospitality... more

Contact
7 Hubbard St, Lenox, MA 01240-2329
(413) 637-2600
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Hotels.com
USD 159*
View Deal
#21 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 4 weeks ago
Charming and elegant

I arrived here I was greeted by the hostess in one of the parlors, there are 2, this old and quaint, beautifully decorated B&B has 5 rooms, 3 of which have their own bathrooms, 2 that share a... more

Reviewed 27 November 2017
Amazing stay

What a jewel Harbour House Inn is. We had a wonderful stay. The house is beautiful and relaxing, in a quiet beautiful location. Jen is a wonderful hostess. Every detail s thought through. Highly... more

Contact
725 N State Rd, Cheshire, MA 01225-9763
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Travelocity
USD 115*
View Deal
#26 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 5 December 2017
Very comfortable, very clean and very well located

What a great find -- 3 mnutes to Kripalu. Lovely, super clean, comfortable and charming rooms. First stay in May/June was extended (two weeks while in instructor training) and the air conditioning... more

Reviewed 26 October 2017
Lovely Stay - Highly Recommended

We loved our stay at Eastgate Inn! Check in was smooth and easy, and the owner was so helpful and welcoming. Our room was super clean, comfy beds and beautiful views of the garden. It you are... more

Contact
207 West St, Lenox, MA 01240-2412
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Race Brook Lodge
USD 111*
View Deal
#28 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 9 December 2017
Woodsy Cabin

This was not our first time at Race Brook. We've stayed with our family, a couple of times, over the years. This time there were 9 of us over the Thanksgiving weekend. We have Thanksgiving dinner... more

Reviewed 27 October 2017
October Hiking

Nice atmosphere and loved being able to hike from the lodge. Very Bohemian style. Great restaurant and staff was very accommodating to my request for gluten free food. Don't expect fancy rooms... more

Contact
864 S Undermountain Rd, Sheffield, MA 01257-9641
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Bar/Lounge
Priceline
USD 242*
View Deal
#29 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 31 October 2017
A True Gem in The Berkshires

Warm, inviting, comfortable, spacious... The Applegate Inn was the highlight of our recent trip to the Northeast. Each room in the Inn is different, so when I phoned, Pam helped me select the room... more

Reviewed 12 September 2017
Great Staff, Food, House, Room and setting -- perfect for honeymoon

We went to Applegate starting August 28 for 5 nights. Can't say enough good things about Pam and her staff. The rooms were really nice, the breakfasts were great. Little touches like brandy at... more

Contact
279 W Park St, Lee, MA 01238-1718
(413) 327-0008
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
SAVE USD 33
USD 211*
Booking.com
USD 178*
View Deal
#31 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 1 week ago
Cute and homey little inn

My girlfriend and I really enjoyed our winter weekend getaway to this inn. The owners of the inn were very nice and accommodating. We had a massive room with a huge comfy bed, a fireplace, and a... more

Reviewed 15 November 2017
Its a real Inn

I read the bad reviews and as usual the reviews were over done. This is a typical old Inn. It has character old pictures and antiques with charm. The Inn is off Rt 7 so easy to get to. The room are... more

Contact
453 Stockbridge Rd, Great Barrington, MA 01230-1233
(413) 207-9318
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Bar/Lounge
Booking.com
USD 79*
View Deal
#32 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 26 August 2017
Comfortable, convenient, relaxing

We stay at the Apple Tree every time we come to Lenox. Totally convenient if you're going to Tanglewood - literally across the street and up the hill! In ground pool overlooking the valley and... more

Reviewed 28 December 2017
A cozy off-season perfectly priced, thoughtful hospitality, a view of the Berkshires and free continental breakfast!

A friend invited me to join her to stay at the Inn last minute. The off season price for 2 queen size beds was $70 a sweet split of $35 each! She came for a day pass yoga workout at Kirpalua and I... more

Contact
10 Richmond Mountain Rd, Lenox, MA 01240-2433
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
Travelocity
USD 245*
View Deal
#33 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 3 weeks ago
Perfection!

My friend and I spent two perfect nights at 33 Main. We visited the Mount, shopped and ate in Lenox, and spent a day at Canyon Ranch. But the highlight of our trip was staying at 33 Main. The inn... more

Reviewed 3 weeks ago
AWESOME!

I have had the good fortune to travel extensively and it is rare that I come across a new experience which leaves me speechless. But it happened this week at 33 Main in Lenox, MA. A small 8 room Inn... more

Contact
33 Main St, Lenox, MA 01240-2311
(413) 400-3333
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Room Service
  • Fitness centre
Booking.com
USD 262*
View Deal
#35 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 1 September 2017
Welcoming and convenient

We felt very welcome at this B&B and enjoyed the breakfasts. Our room was smaller than I realized when booking on line, but we enjoyed the large living room and front porch. I love being in town with... more

Reviewed 27 June 2017
Great location and nice place

Nice room, beautiful Victorian style home and very nice breakfast. I would give this place 5 stars but when we arrived there was no record of our reservation upon arrival. If there weren't a... more

Contact
11 Old Stockbridge Rd, Post Office Box 1717, Lenox, MA 01240-2415
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Booking.com
USD 109*
View Deal
#36 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 3 weeks ago
December Stay at the Cottage

I had a wonderful stay at the Cottage during the Xmas holiday. The place is lovely. The location is ideal for any season in the Berkshires. Its serenity, relaxed and scenic environment is... more

Reviewed 24 October 2017
Roomy, Convenient, and Close

Our accommodations were very spacious for our family, mom, dad, and two grown sons. The continental breakfast was perfect as there was no rush to get up in the morning and plenty for us to eat. We... more

Contact
Prospect Hill Road, Stockbridge, MA 01262
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Hotels.com
USD 109*
View Deal
#37 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 2 weeks ago
Perfect place to stay

We really enjoyed our stay here. This B&B had a comfortable bed, soft sheets, warm water and nice shower pressure. We’ve stayed so many “expensive” places that did not have these must-haves... more

Reviewed 3 weeks ago
Wonderful hosts and place!

Timothy and Donna went 'above and beyond' in hosting my husband and I when we were in a jam. Their place is beautiful, spacious, and homey. We had a very comfortable nights sleep as well. The family... more

Contact
1120 Main St, Williamstown, MA 01267-2636
Amenities
  • Free Wifi
  • Free Parking
Booking.com
USD 154*
View Deal
#38 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 17 October 2017
Super-rural but very nice!

I chose Maple House B&B as a stopover on our way through from Lake Placid to Martha's Vineyard. Rebecca advised that we should eat before we arrived as there is nothing in Rowe, so we did just that... more

Reviewed 18 June 2017
Its like "going over the River and Through the Woods" to Grandma's house.

I love the village of Rowe. In fact this trip was to view a house as a summer retreat from super hot Arizona(we are in the process of buying it - yay!). The Maple House is a beautiful old farm... more

Contact
51 Middletown Hill Rd, Rowe, MA 01367-9702
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Beachfront
Booking.com
USD 137*
View Deal
#40 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 6 November 2017
The Perfect Place to Stay in Stockbridge

Thanks to Joanne and Jim for our wonderful stay at their clean, comfortable, and friendly B&B. We loved every minute including our fantastic breakfast of a fresh fruit salad, spinach omelette... more

Reviewed 24 August 2017
Joann and jim are cunsummate B+ B proprietors. They attract interesting guests, and they themselves and their staff are

Comfortable relaxing and oh that pool! The property is soothing...There's nothing like starting the day with a dip....the large pieces oif art work/scupltures help make the property even more... more

Contact
11 East Street, Route 7 N., PO Box 191, Stockbridge, MA 01262
+1 888-267-6101
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
Travelocity
USD 238*
View Deal
#60 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 1 February 2016
Winter Weekend

We stayed here the last weekend in January 2016 hoping to do some xcountry skiing on their fabulous trails but with temps in the 50s and the lack of snow, we had to find other things to do. Armed... more

Reviewed 4 August 2015
Charming + cozy

The hosts are really friendly and nice. I've stayed here several times when I've visited Jacob's Pillow. They have a lovely garden and it's a quiet spot on a farm. In the winter they do cross... more

Contact
1986 Fred Snow Rd, Becket, MA 01223-9776
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Restaurant
  • Fitness centre
TripAdvisor
View Deal
#1 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 17 December 2017
Stockbridge

1st Class B&B. Amanda and Jose offered great hospitality.It is a lovely home within walking distance of downtown. We had a cozy room with a fireplace. Breakfast was delicious. Cheese plates were... more

Reviewed 12 December 2017
Very nice Pre-Christmas get away in the Berkshires

We chose to stay at the 1862 Seasons on Main for several reasons. The first was that you can't possibly beat the location - right on the edge of town, and right on main street. The other was that it... more

Contact
47 Main St, Stockbridge, MA 01262-9701
(413) 284-4479
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
TripAdvisor
View Deal
#11 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 14 January 2018
Great Breakfasts

Fantastic Breakfasts, fantastic couple that run the joint. Can't recommend it more. They showed us where to go on runs nearby, where to go out to eat. I really can't rave about their breakfasts more... more

Reviewed 2 January 2018
Amazing Hospitality and Food

Robert and Robbie greeted us upon arrival with a warm fire and a glass of wine, a wonderful start to a relaxing if bone chilling weekend (December 28-30, 2017) in Great Barrington. We enjoyed getting... more

Contact
1 Prospect Lake Rd, Great Barrington, MA 01230-9003
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
No availability for your dates from these sites
#13 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Special offer
Offers & AnnouncementsThe Manor Loves February!
Reviews
Reviewed 29 November 2017
The perfect weekend.

We couldn't have had a nicer time at the Manor. It's the perfect combination of luxury, privacy and intimacy. Lesa is a warm, natural and exceptionally thoughtful hostess who truly loves what she... more

Reviewed 31 October 2017
A most gracious hostess

My wife and I were planning to do some hiking in the northern Berkshires and came across Blackington Manor, probably through this website. We have stayed at B&B's before but have never experienced... more

Contact
1391 Massachusetts Ave, North Adams, MA 01247-2238
(413) 258-5605
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
TripAdvisor
View Deal
#17 of 94 Berkshires B&B and Inns
  • Free Wifi
  • Free Parking
Reviews
Reviewed 14 November 2017
Worth a Trip Back

After looking at different places to stay in Pittsfield, selected the White Horse Inn and couldn't have been more pleased. The hosts went out of their way to create a welcoming and cozy stay. Amazing... more

Reviewed 14 November 2017
Our favorite Inn!

We have stayed at the White Horse Inn every year for the past seven years and we are NEVER disappointed! We love the room, the ambiance, the amazing breakfast, the hospitality and most of all - the... more

Contact
378 South St, Pittsfield, MA 01201-6804
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
* Prices are provided by our partners, and reflect average nightly room rates, including taxes and fees that are fixed, known to our partners, and due at time of booking. Please see our partners for more details.
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