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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Feb 20 - Feb 22
In two weeks
Feb 27 - Mar 1
In one month
Mar 13 - Mar 15
In two months
Apr 10 - Apr 12

Our top choices for Windsor bed & breakfast

1 bedroom, WiFi

Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
$150 nightly
The price is $151
Feb 15 - Feb 16
Total with taxes and fees
Cozy Retreat in historic Farmhouse - Tranquility Room
Exterior

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
$212 nightly
The price is $224
Feb 21 - Feb 22
Total with taxes and fees
UU Rowe Camp and Conference Center
1 bedroom, WiFi

Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
$135 nightly
The price is $136
Feb 16 - Feb 17
Total with taxes and fees
Cozy Farmhouse Retreat - Ram Dass Room
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, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
$163 nightly
The price is $182
Mar 7 - Mar 8
Total with taxes and fees
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)
"Great place, great hosts, lovely experience. Would go back 100x. "
United States
Jared
$241 nightly
The price is $255
Feb 23 - Feb 24
Total with taxes and fees
Harbour House Inn
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
$151 nightly
The price is $169
Feb 15 - Feb 16
Total with taxes and fees
Lakehouse Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
$106 nightly
The price is $117
Mar 1 - Mar 2
Total with taxes and fees
Shaker Mill Inn
2 bedrooms, WiFi

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, (2 reviews)
"The piano, large spaces, and fireplace were all much appreciated."
United States
Benjamin B.
$150 nightly
The price is $151
Feb 15 - Feb 16
Total with taxes and fees
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Feb 16 - Feb 17
Total with taxes and fees
Chambery Inn
Front of property

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
$251 nightly
The price is $280
Feb 22 - Feb 23
Total with taxes and fees
The Inn at Stockbridge
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$269 nightly
The price is $300
Feb 16 - Feb 17
Total with taxes and fees
Devonfield Inn B&B
Exterior

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
$402 nightly
The price is $450
Feb 25 - Feb 26
Total with taxes and fees
33 Main
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$315 nightly
The price is $352
Mar 7 - Mar 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
$575 nightly
The price is $631
Feb 16 - Feb 17
Total with taxes and fees
Inn at Kenmore Hall
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
$137 nightly
The price is $154
Feb 18 - Feb 19
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
$139 nightly
The price is $156
Mar 3 - Mar 4
Total with taxes and fees
Inn at Silver Maple Farm
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$253 nightly
The price is $290
Feb 18 - Feb 19
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Interior

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$291 nightly
The price is $333
Feb 17 - Feb 18
Total with taxes and fees
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
$309 nightly
The price is $353
Feb 15 - Feb 16
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$253 nightly
The price is $290
Feb 18 - Feb 19
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything! :)"
Joanie 5-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Windsor

Windsor B&B information

Number of reviews
2,345
Accommodation
35 B&B
Lowest Price
$117
Highest Price
$631

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 $117 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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