Find a Bed and Breakfast in Windsor from CA $210

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Check prices for these dates

Next weekend
Jun 19 - Jun 21
In two weeks
Jun 26 - Jun 28
In one month
Jul 10 - Jul 12
In two months
Aug 7 - Aug 9

Our top choices for Windsor bed & breakfast

Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is CA $242
CA $270 total
includes taxes & fees
Jun 9 - Jun 10
The Trail in Adams - Berkshires’ Art Hotel
Exterior

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 $325
CA $344 total
includes taxes & fees
Jun 9 - Jun 10
Harbour House Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (378 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 $238
CA $266 total
includes taxes & fees
Jun 11 - Jun 12
Chambery Inn
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $459
CA $512 total
includes taxes & fees
Jun 14 - Jun 15
Devonfield Inn B&B
Property grounds

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 $252
CA $282 total
includes taxes & fees
Jun 16 - Jun 17
Whistler's Inn Bed & Breakfast
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $345
CA $448 total
includes taxes & fees
Jun 9 - Jun 10
Experience Timeless Elegance in The Edith Wharton Room!
Luxury Room, 1 King Bed, Bathtub

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 $881
CA $985 total
includes taxes & fees
Jun 14 - Jun 15
33 Main
Shower, towels

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 $345
CA $448 total
includes taxes & fees
Jun 9 - Jun 10
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 $434
CA $565 total
includes taxes & fees
Jun 14 - Jun 15
Elegant Carriage House room with a queen bed and private patio.
Interior

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 $456
CA $593 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $479
CA $624 total
includes taxes & fees
Jun 10 - Jun 11
Historic Susan B. Anthony Room - Cozy & Charming Stay
Exterior

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)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is CA $211
CA $242 total
includes taxes & fees
Jun 9 - Jun 10
The Cornell Inn, Lenox & The Berkshires
1 bedroom, bed sheets

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 $579
CA $753 total
includes taxes & fees
Jun 9 - Jun 10
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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 $690
CA $898 total
includes taxes & fees
Jun 10 - Jun 11
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Shower, towels

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $624
CA $793 total
includes taxes & fees
Jun 10 - Jun 11
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $690
CA $898 total
includes taxes & fees
Jun 9 - Jun 10
Elegant suite with a king bed, fireplace, and kitchenette.
Suite, Private Bathroom (RedBird Suite) | View from room

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 $460
CA $557 total
includes taxes & fees
Jun 21 - Jun 22
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (460 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $191
CA $210 total
includes taxes & fees
Jun 10 - Jun 11
Shaker Mill Inn
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is CA $592
CA $650 total
includes taxes & fees
Jun 12 - Jun 13
Inn at Kenmore Hall
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is CA $236
CA $264 total
includes taxes & fees
Jun 23 - Jun 24
Inn at Silver Maple Farm
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

10/10 Excellent
"Spacious and clean room, great location, friendly staff"
Theresa 1-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Windsor

Windsor B&B information

Number of reviews
2,362
Accommodation
46 B&B
Lowest Price
CA $210
Highest Price
CA $985

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. 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.
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.

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