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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Windsor bed & breakfast

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.

1. 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, (158 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
$151 nightly
The price is $169
Nov 5 - Nov 6
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

2. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
$254 nightly
The price is $268
Oct 29 - Oct 30
Total with taxes and fees
Harbour House Inn
A red building with a sign reading "Shaker Mill Inn."

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$110 nightly
The price is $121
Nov 2 - Nov 3
Total with taxes and fees
Shaker Mill Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (521 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$121 nightly
The price is $135
Nov 6 - Nov 7
Total with taxes and fees
Whistler's Inn Bed & Breakfast
A house with a chimney, surrounded by trees with autumn foliage.

5. 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
$149 nightly
The price is $157
Oct 29 - Oct 30
Total with taxes and fees
UU Rowe Camp and Conference Center
Room

6. 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.
$150 nightly
The price is $151
Oct 29 - Oct 30
Total with taxes and fees
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

7. 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
$184 nightly
The price is $206
Nov 22 - Nov 23
Total with taxes and fees
Inn at Silver Maple Farm
A two-story building with a sign reading "Chambéry Inn".

8. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
$201 nightly
The price is $225
Nov 2 - Nov 3
Total with taxes and fees
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

9. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$369 nightly
The price is $412
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
Room

10. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
$110 nightly
The price is $111
Oct 29 - Oct 30
Total with taxes and fees
Cozy Farmhouse Retreat - Ram Dass Room
Front of property

11. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
$383 nightly
The price is $428
Nov 12 - Nov 13
Total with taxes and fees
The Inn at Stockbridge
A snow-covered outdoor area with a patio, seating, and a covered dining area.

12. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$178 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Room

13. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
$150 nightly
The price is $151
Oct 29 - Oct 30
Total with taxes and fees
Cozy Retreat in historic Farmhouse - Tranquility Room
A two-story house with a brick entrance and a white facade.

14. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$381 nightly
The price is $425
Nov 13 - Nov 14
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

15. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$310 nightly
The price is $355
Nov 1 - Nov 2
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$344 nightly
The price is $394
Nov 1 - Nov 2
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
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
$362 nightly
The price is $414
Nov 1 - Nov 2
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
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.

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$326 nightly
The price is $373
Nov 4 - Nov 5
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$310 nightly
The price is $355
Nov 1 - Nov 2
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

20. 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
$447 nightly
The price is $511
Nov 1 - Nov 2
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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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Top Windsor Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"The room was clean and the staff was friendly and helpful. Lots of parking . The hot tub was nice after a day of biking."
Kathleen 2-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Windsor

Windsor B&B information

Number of reviews
1,862
Accommodation
46 B&B
Lowest Price
$111
Highest Price
$511

Frequently asked questions

What is the nightly rate for a B&B in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $111 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Windsor B&B and a hotel?
Every Windsor B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windsor B&Bs.

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