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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

Our top choices for Windsor bed & breakfast

Terrace/patio

1. 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, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is AU$267
includes taxes & fees
22 Sept - 23 Sept
The Trail in Adams - Berkshires’ Art Hotel
Exterior

2. 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
The price is AU$342
includes taxes & fees
9 Sept - 10 Sept
Harbour House Inn
Garden

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$225
includes taxes & fees
9 Sept - 10 Sept
Shaker Mill Inn
Property grounds

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AU$275
includes taxes & fees
1 Oct - 2 Oct
Whistler's Inn Bed & Breakfast
Front of property

5. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 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 AU$418
includes taxes & fees
9 Sept - 10 Sept
Chambery Inn
Front of property – evening/night

6. 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
The price is AU$633
includes taxes & fees
14 Sept - 15 Sept
Devonfield Inn B&B
Aerial view

7. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (116 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
The price is AU$355
includes taxes & fees
14 Sept - 15 Sept
Inn at Silver Maple Farm
Front of property

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AU$613
includes taxes & fees
14 Sept - 15 Sept
The Inn at Stockbridge
Room

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$572
includes taxes & fees
10 Sept - 11 Sept
Experience Timeless Elegance in The Edith Wharton Room!
Suite, Private Bathroom (RedBird Suite) | View from room

10. 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, (117 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AU$554
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Interior

11. 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 AU$600
includes taxes & fees
10 Sept - 11 Sept
Elegant Carriage House room with a queen bed and private patio.
Exterior

12. 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)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
The price is AU$323
includes taxes & fees
14 Sept - 15 Sept
The Cornell Inn, Lenox & The Berkshires
Interior

13. 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 AU$629
includes taxes & fees
10 Sept - 11 Sept
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$656
includes taxes & fees
10 Sept - 11 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
Room

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AU$572
includes taxes & fees
10 Sept - 11 Sept
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Room

16. 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 AU$796
includes taxes & fees
9 Sept - 10 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Living area

17. 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 AU$950
includes taxes & fees
14 Sept - 15 Sept
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AU$952
includes taxes & fees
9 Sept - 10 Sept
Elegant suite with a king bed, fireplace, and kitchenette.
Room

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AU$834
includes taxes & fees
14 Sept - 15 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Front of property

20. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AU$354
includes taxes & fees
9 Sept - 10 Sept
Brook Farm 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.
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Top Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"The Inn is very welcoming with a broad front porch filled with wicker chairs and rockers. Inside there are many sitting rooms, a restaurant and tavern, gift and floral shops and access to an outdoor pool. Well loved antiques are everywhere for comfortable seating throughout the property. Rooms facing the streets can be noisy with traffic. Lots of atmosphere, history and great location for shopping, sightseeing and dining."
Catherine 7-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Windsor

Windsor B&B information

Number of reviews
2,084
Accommodation
46 B&B
Lowest Price
AU$225
Highest Price
AU$633

Frequently asked questions

Searching for B&Bs in Windsor?
If you want to find somewhere to stay with fewer rooms than a hotel and a more personalised 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 garden for guests to admire or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Windsor?
Here are some well-liked 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 decor. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 8.6 mi (13.9 km) from the city centre. Enjoy the unique decor and patio area. Whistler's Inn Bed & Breakfast: 14 rooms. Located 15.8 mi (25.4 km) from the core of Windsor. Enjoy the private garden and unique decor.
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 temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
How can I get to and around Windsor?
You can map out your trip in and around Windsor ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away. 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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