Find a Bed and Breakfast in Windsor from CA $155

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Windsor bed & breakfast

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 $277
CA $292 total
includes taxes & fees
Apr 24 - Apr 25
UU Rowe Camp and Conference Center

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
8.8 out of 10, Excellent, (146 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
The price is CA $237
CA $265 total
includes taxes & fees
May 19 - May 20
The Trail in Adams - Berkshires’ Art Hotel

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $319
CA $337 total
includes taxes & fees
Apr 27 - Apr 28
Harbour House Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $234
CA $261 total
includes taxes & fees
Apr 26 - Apr 27
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is CA $409
CA $456 total
includes taxes & fees
Apr 27 - Apr 28
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $359
CA $421 total
includes taxes & fees
May 5 - May 6
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is CA $314
CA $351 total
includes taxes & fees
May 19 - May 20
Whistler's Inn Bed & Breakfast

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $733
CA $818 total
includes taxes & fees
Apr 26 - Apr 27
33 Main

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $294
CA $383 total
includes taxes & fees
May 4 - May 5
Experience Timeless Elegance in The Edith Wharton Room!

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is CA $141
CA $155 total
includes taxes & fees
Apr 27 - Apr 28
Shaker Mill Inn

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $423
CA $512 total
includes taxes & fees
May 5 - May 6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 $360
CA $466 total
includes taxes & fees
May 4 - May 5
Elegant Carriage House room with a queen bed and private patio.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is CA $177
CA $203 total
includes taxes & fees
May 6 - May 7
The Cornell Inn, Lenox & The Berkshires

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 $294
CA $383 total
includes taxes & fees
May 4 - May 5
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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 $382
CA $494 total
includes taxes & fees
May 4 - May 5
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $404
CA $522 total
includes taxes & fees
May 4 - May 5
Historic Susan B. Anthony Room - Cozy & Charming Stay

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 $502
CA $654 total
includes taxes & fees
May 4 - May 5
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $546
CA $693 total
includes taxes & fees
May 4 - May 5
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is CA $611
CA $796 total
includes taxes & fees
May 4 - May 5
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $611
CA $796 total
includes taxes & fees
May 4 - May 5
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

Windsor B&B information

Number of reviews
1,887
Accommodation
45 B&B
Lowest Price
CA $155
Highest Price
CA $818

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?
Below are some well-liked B&Bs in the 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. Chambery Inn: 9 rooms. Situated 17.4 mi (28 km) from the heart of Windsor. Enjoy the private yard and deli. Lakehouse Inn: 14 rooms. 16.8 mi (27 km) from the heart of downtown. Enjoy the free full breakfast and deli. Whistler's Inn Bed & Breakfast: 14 rooms. Located 15.8 mi (25.4 km) from the core of Windsor. Enjoy the private yard and unique décor.
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