Default HTG hotel image

Find a Bed and Breakfast in Windsor from CA $156

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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
The price is CA $210
CA $235 total
includes taxes & fees
Nov 29 - Nov 30
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
The price is CA $355
CA $375 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is CA $155
CA $170 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is CA $169
CA $189 total
includes taxes & fees
Nov 6 - Nov 7
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
The price is CA $188
CA $198 total
includes taxes & fees
Oct 31 - Nov 1
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.
The price is CA $182
CA $211 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $257
CA $288 total
includes taxes & fees
Nov 24 - Nov 25
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
The price is CA $246
CA $274 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is CA $516
CA $577 total
includes taxes & fees
Nov 5 - Nov 6
Devonfield Inn B&B
Room

10. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is CA $126
CA $156 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $510
CA $599 total
includes taxes & fees
Nov 12 - Nov 13
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
The price is CA $238
CA $273 total
includes taxes & fees
Nov 10 - Nov 11
The Cornell Inn, Lenox & The Berkshires
Room

13. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is CA $182
CA $211 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $502
CA $608 total
includes taxes & fees
Nov 27 - Nov 28
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
The price is CA $380
CA $497 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $425
CA $556 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $447
CA $584 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $402
CA $525 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $380
CA $497 total
includes taxes & fees
Nov 5 - Nov 6
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
The price is CA $548
CA $716 total
includes taxes & fees
Nov 12 - Nov 13
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very charming, particularly the main house. We were at another structure off the main place which was perfectly nice but perhaps less charming."
Diane 1-night trip
Posted 15 hours ago
The Red Lion Inn

Find out more about Windsor

Windsor B&B information

Number of reviews
1,862
Accommodation
46 B&B
Lowest Price
CA $156
Highest Price
CA $716

Frequently asked questions

Searching for B&Bs in Windsor?
If you want to find an accommodation with fewer rooms than the traditional hotel and a cozy environment, a B&B may be the perfect thing for your trip to Windsor.
How do you know if a B&B is the right choice for you?
B&Bs all have a unique charm. Whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Windsor?
Here are some B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 15.6 mi (25.1 km) from the heart of Windsor. Enjoy the free full breakfast and unique décor. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 8.6 mi (13.9 km) from the heart of downtown. Enjoy the unique décor and patio area. Chambery Inn: 9 rooms. Located 17.4 mi (28 km) from the core of Windsor. Enjoy the private yard and deli.
When is the best time to book my B&B in Windsor?
When you're planning your escape to Windsor, 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 Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to and around Windsor?
Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia