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Compare 17 B&B in New Ashford with updated reviews, rates, and availability.

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
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
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (399)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is AED 533
AED 584 total
includes taxes & fees
17 Nov - 18 Nov
Shaker Mill Inn
South Shire
Front of property
South Shire
4.0 star property
9.2 out of 10, Wonderful, (75)
"Rather unique We liked the piano player "
The price is AED 694
AED 819 total
includes taxes & fees
18 Nov - 19 Nov
South Shire
Inn at Silver Maple Farm
Front of property
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (79)
"A perfect place to enjoy fall colors. Generous and delicious breakfast."
The price is AED 584
AED 631 total
includes taxes & fees
25 Nov - 26 Nov
Inn at Silver Maple Farm
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (69)
"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
The Four Chimneys Inn
Exterior
The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, (272)
"What a charming B&B . So warming and inviting.Staff made you feel at home and were all so kind and friendly.Oh and the food was delicious,"
The price is AED 915
AED 997 total
includes taxes & fees
18 Nov - 19 Nov
The Four Chimneys Inn
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
Inn at Kenmore Hall
Front of property
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
Inn at Kenmore Hall
Berkshire Mountain House
View from property
Berkshire Mountain House
3.0 star property
9.4 out of 10, Exceptional, (24)
"Mona was an excellent host. Our bed was very comfortable and the food was good, too! I'd definitely recommend staying here as there's so much to do in the area."
Berkshire Mountain House
Chesapeake Inn of Lenox
Exterior
Chesapeake Inn of Lenox
3.0 star property
7.2 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
Victorian mansion's Jim-Dandy Suite
Bedroom
Victorian mansion's Jim-Dandy Suite
10.0 out of 10, Exceptional, (5)
"It was such a relief to enter a space that honors a time gone by. The attention to detail—perfect touches—from the sheets and pillows tot he fresh flowers at the breakfast table added to the hospitality and warmth we felt immediately walking into the inn. There is NOTHING like staying at a place where the owner is present and attending to guests//thank you, Jim for a lovely respite from the circus."
Victorian mansion's Jim-Dandy Suite
Victorian mansions Coach Room with Breakfast
Coach Bedroom
Victorian mansions Coach Room with Breakfast
Victorian mansions Coach Room with Breakfast
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 New Ashford

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
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (223)
"One of the best properties i've ever stayed at "
The price is AED 481
AED 751 total
includes taxes & fees
18 Nov - 19 Nov
Berkshire Village Carriage House - Super Private!!
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 New Ashford?
Whether you’re passing through town and are looking for an accommodation that’s small and charming, or you’re traveling solo and hoping to get some local recommendations, a B&B might be the right choice for your trip. If your ideal vacation to New Ashford includes spending lots of time outside, Mount Greylock State Reservation is a good spot to enjoy the scenery.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to meet guests from other places, and tasty breakfasts, B&Bs all have a one-of-a-kind setting.
What are the top B&Bs in New Ashford?
Here are some B&Bs in the surrounding area: The Cornell Inn, Lenox: 16.7 mi (26.8 km) from the heart of New Ashford. Enjoy the free full breakfast and unique décor. Brook Farm Inn: 15 rooms. 17.6 mi (28.4 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Whistler’s Inn Bed & Breakfast: 14 rooms. Located 16.9 mi (27.2 km) from the core of New Ashford. Enjoy the private yard and unique décor.
When should I book my B&B in New Ashford?
When you’re dreaming of a trip to New Ashford, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in New Ashford are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in New Ashford?
If you want to check out some popular attractions in New Ashford, you might enjoy a visit to Mount Greylock State Reservation. You might also consider a trip to sites like Brodie Mountain or Williamstown Theatre Festival if you have time to see more of the area.
How can I get to and around New Ashford?
You can plan your excursions in and around New Ashford ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 12.7 mi (20.5 km) away from the city center. Otherwise, look for flights into Albany Intl. Airport (ALB), which is 30.5 mi (49.2 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.