Photo by The Curious Zephyr

Find a Bed and Breakfast in New Ashford from CA $126

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for New Ashford bed & breakfast

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $295
CA $312 total
includes taxes & fees
Dec 2 - Dec 3
Harbour House Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

2. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $239
CA $267 total
includes taxes & fees
Dec 8 - Dec 9
The Trail in Adams - Berkshires’ Art Hotel
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

3. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is CA $230
CA $257 total
includes taxes & fees
Dec 6 - Dec 7
Inn at Silver Maple Farm
A house with a chimney, surrounded by trees with autumn foliage.

4. UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is CA $139
CA $146 total
includes taxes & fees
Nov 8 - Nov 9
UU Rowe Camp and Conference Center
A red building with a sign reading "Shaker Mill Inn."

5. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is CA $203
CA $223 total
includes taxes & fees
Nov 9 - Nov 10
Shaker Mill Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
The price is CA $192
CA $214 total
includes taxes & fees
Nov 8 - Nov 9
Whistler's Inn Bed & Breakfast
A room with wooden paneling, a piano, a chair, and a door leading to another room.

7. South Shire

South Shire
4.0 star property
Bennington
9.0 out of 10, Wonderful, (141 reviews)
"Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants."
United States
Jeffrey
The price is CA $225
CA $261 total
includes taxes & fees
Nov 21 - Nov 22
South Shire
A large, two-story house with a covered porch and multiple chimneys.

8. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.6 out of 10, Exceptional, (291 reviews)
"We enjoyed our stay."
United States
Robert
The price is CA $314
CA $342 total
includes taxes & fees
Nov 23 - Nov 24
The Four Chimneys Inn
Room

9. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is CA $126
CA $144 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Farmhouse Retreat - Ram Dass Room
Room

10. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (3 reviews)
"Great space."
United States
Andrew S.
The price is CA $182
CA $200 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
A snow-covered outdoor area with a patio, seating, and a covered dining area.

11. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,002 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is CA $238
CA $273 total
includes taxes & fees
Nov 9 - Nov 10
The Cornell Inn, Lenox & The Berkshires
Room

12. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is CA $182
CA $200 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Retreat in historic Farmhouse - Tranquility Room
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

13. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is CA $403
CA $501 total
includes taxes & fees
Nov 9 - Nov 10
Elegant Carriage House room with a queen bed and private patio.
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

14. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $380
CA $474 total
includes taxes & fees
Nov 9 - Nov 10
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

15. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is CA $425
CA $528 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Carriage House room with a double bed and private balcony
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

16. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $380
CA $474 total
includes taxes & fees
Nov 9 - Nov 10
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $448
CA $557 total
includes taxes & fees
Nov 9 - Nov 10
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

18. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is CA $549
CA $683 total
includes taxes & fees
Nov 9 - Nov 10
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $593
CA $721 total
includes taxes & fees
Nov 9 - Nov 10
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sofa, a coffee table, and a fireplace.

20. Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $661
CA $822 total
includes taxes & fees
Nov 12 - Nov 13
Elegant suite with a king bed, fireplace, and kitchenette.
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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Learn more about New Ashford

Come to upscale New Ashford and enjoy its skiing, mountain views, and festivals.

See all hotels in New Ashford
A forest with tall trees and a small wooden shelter.
Photo by The Curious Zephyr
Open Photo by The Curious Zephyr

Top reviews in New Ashford

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
Adams

10/10 Excellent

Incredible staff, free parking and cute rooms!
Canada
Priscilla
Reviewed May 18, 2026
The Trail in Adams - Berkshires’ Art Hotel

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. When you want to explore some attractions in town, Mount Greylock State Reservation and Green River Wildlife Management Area are worth a stop.

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 well-liked B&Bs in the area: The Cornell Inn, Lenox & The Berkshires: 16.7 mi (26.8 km) from the heart of New Ashford. Enjoy the free full breakfast and unique décor. Inn at Silver Maple Farm: 11 rooms. 17.2 mi (27.7 km) from the downtown core. Enjoy the free buffet breakfast and designer toiletries. The Trail in Adams - Berkshires’ Art Hotel: 9 rooms. Located 6.2 mi (10 km) from the core of New Ashford. Enjoy the unique décor and patio area.

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?

When you want to explore some things to do in town, Mount Greylock State Reservation and Green River Wildlife Management Area are some notable sights to visit. 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.

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