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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Windsor bed & breakfast

Exterior

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
$221 nightly
The price is $233
Sep 10 - Sep 11
Total with taxes and fees
Harbour House Inn
Terrace/patio

2. 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, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
$203 nightly
The price is $226
Sep 14 - Sep 15
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Property grounds

3. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (514 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$159 nightly
The price is $178
Sep 13 - Sep 14
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Garden

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (467 reviews)
"Wonderful place to stay!"
United States
Mervin
$173 nightly
The price is $190
Sep 8 - Sep 9
Total with taxes and fees
Shaker Mill Inn
Front of property

5. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (384 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
$300 nightly
The price is $335
Aug 23 - Aug 24
Total with taxes and fees
Chambery Inn
Aerial view

6. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (113 reviews)
"Very nice hotel."
United States
Erdem
$139 nightly
The price is $156
Aug 25 - Aug 26
Total with taxes and fees
Inn at Silver Maple Farm
Front of property - evening/night

7. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
$389 nightly
The price is $435
Sep 3 - Sep 4
Total with taxes and fees
Devonfield Inn B&B
Front of property

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (102 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
$396 nightly
The price is $442
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge
1 bedroom, WiFi, bed sheets

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$354 nightly
The price is $405
Aug 24 - Aug 25
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

10. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
$698 nightly
The price is $779
Sep 7 - Sep 8
Total with taxes and fees
33 Main
Exterior

11. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
$202 nightly
The price is $224
Aug 24 - Aug 25
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Suite, Private Bathroom (RedBird Suite) | View from room

12. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Interior

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$383 nightly
The price is $438
Sep 8 - Sep 9
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$354 nightly
The price is $405
Aug 24 - Aug 25
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$392 nightly
The price is $449
Aug 31 - Sep 1
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

16. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$411 nightly
The price is $470
Aug 31 - Sep 1
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, bed sheets

17. 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
$493 nightly
The price is $564
Aug 31 - Sep 1
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets

18. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$529 nightly
The price is $591
Aug 26 - Aug 27
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace

19. 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
$584 nightly
The price is $668
Aug 25 - Aug 26
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$584 nightly
The price is $668
Aug 25 - Aug 26
Total with taxes and fees
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.
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Top Windsor Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."
Jen 1-night trip
Posted 5 hours ago
Howard Johnson by Wyndham Lenox

Find out more about Windsor

Windsor B&B information

Number of reviews
2,119
Accommodation
46 B&B
Lowest Price
$156
Highest Price
$779

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 $156 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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