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Compare 24 B&B in Cummington with updated reviews, rates, and availability.

The Ellery
Exterior
The Ellery
3.5 star property
9.0 out of 10, Wonderful, (530)
"The room was great, exactly what I expected and nice. Nothing lavish or opulent but was very nice. Very nice shampoo and toiletries The breakfast was AMAZING and I really really really value that. The nook is very cute and the food was to die for. Check in and check out was seamless, I didn't talk to a single person and had no issues. Which is super nice for quiet solo travel. "
The price is AED 511
AED 570 total
includes taxes & fees
17 Nov - 18 Nov
The Ellery
The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1000)
"Perfect romantic spot for a weekend getaway. Close enough to walk into town but far enough from crowds "
The price is AED 448
AED 526 total
includes taxes & fees
17 Nov - 18 Nov
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is AED 547
AED 642 total
includes taxes & fees
15 Nov - 16 Nov
Lakehouse Inn
Black Walnut Inn
Front of property
Black Walnut Inn
2.0 star property
9.8 out of 10, Exceptional, (33)
"Beautiful inn with a delicious breakfast and warm, gracious hosts. Our children loved feeding their chickens!"
The price is AED 660
AED 737 total
includes taxes & fees
17 Nov - 18 Nov
Black Walnut Inn
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is AED 698
AED 779 total
includes taxes & fees
17 Nov - 18 Nov
Chambery Inn
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (471)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is AED 509
AED 638 total
includes taxes & fees
18 Nov - 19 Nov
Whistler's Inn Bed & Breakfast
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (121)
"Stayed only one night Very cosy, quiet place "
The price is AED 592
AED 662 total
includes taxes & fees
17 Nov - 18 Nov
The Trail in Adams - Berkshires’ Art Hotel
Old Mill Inn
Living area
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (463)
"Beautiful place. Great staff. Clean and convenient "
The price is AED 696
AED 778 total
includes taxes & fees
18 Nov - 19 Nov
Old Mill Inn
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (68)
"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! "
The price is AED 1,285
AED 1,436 total
includes taxes & fees
25 Nov - 26 Nov
33 Main
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is AED 713
AED 796 total
includes taxes & fees
25 Nov - 26 Nov
Brook Farm Inn
Daniel Stebbins House
Exterior
Daniel Stebbins House
3.0 star property
10.0 out of 10, Exceptional, (45)
"What is not to love about being welcomed into Richard and Ruth’s home. They are wonderful hosts and spent hours talking to us both during our stay. The house is an amazing building and learning about its history was wonderful. We walked into the tiny town and got some dinner, lovely options available. We can not wait to visit again and will be recommending anyone travelling around this area should certainly book a stay."
The price is AED 993
AED 1,049 total
includes taxes & fees
15 Nov - 16 Nov
Daniel Stebbins House
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (117)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is AED 988
AED 1,104 total
includes taxes & fees
17 Nov - 18 Nov
Devonfield Inn B&B
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Harbour House Inn
Room
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 963
AED 1,018 total
includes taxes & fees
18 Nov - 19 Nov
Harbour House Inn
Eastgate Inn B&B
Front of property
Eastgate Inn B&B
2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Bathroom
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Room
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
19 Nov - 20 Nov
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Interior
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
10.0 out of 10, Exceptional, (6)
The price is AED 3,673
AED 4,685 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
8.4 out of 10, Very Good, (10)
"Room was not what i reserverd I left inn and need a refund Spent an hour on the phone with Travelocity Outside inn trying to resolve reservation With no resolve I left Inn "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cummington

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AED 547
AED 600 total
includes taxes & fees
15 Nov - 16 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Cummington?
If you want to find an accommodation with a small number of rooms and a more personalized environment, a bed and breakfast might be the perfect option for your trip to Cummington. When you want to explore some attractions in town, Swift River and Westfield River are worth a stop.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to meet other guests, and top-rated breakfasts, B&Bs offer a one-of-a-kind setting.
What are the best bed and breakfasts in Cummington?
Here are some B&Bs in the surrounding area: The Ellery: 15.7 mi (25.2 km) from the heart of Cummington.Old Mill Inn: 12 rooms. 15.6 mi (25.1 km) from the heart of downtown. Enjoy the deli and unique décor.
What's the best time of year to book my B&B in Cummington?
When you’re dreaming of a trip to Cummington, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Cummington are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Cummington?
When you want to spend some time in the great outdoors, Swift River and Westfield River are some notable spots. Chesterfield Gorge and Berkshire East Ski Resort are also some sites to visit if you want to see more of the area.
How can I get to and around Cummington?
You can plan your excursions in and around Cummington ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 20.5 mi (33.1 km) away from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 22 mi (35.3 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.