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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Featured B&B in Windsor

Front of property
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

2.0 star property
Rowe
The price is AU$244
includes taxes & fees
2 Dec - 3 Dec
UU Rowe Camp and Conference Center
Terrace/patio
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, (141)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AU$301
includes taxes & fees
2 Dec - 3 Dec
The Trail in Adams - Berkshires’ Art Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is AU$199
includes taxes & fees
2 Dec - 3 Dec
Shaker Mill Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AU$334
includes taxes & fees
4 Dec - 5 Dec
Lakehouse Inn
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AU$408
includes taxes & fees
1 Dec - 2 Dec
Harbour House Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is AU$456
includes taxes & fees
23 Nov - 24 Nov
The Inn at Stockbridge
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
The price is AU$479
includes taxes & fees
30 Nov - 1 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is AU$210
includes taxes & fees
23 Nov - 24 Nov
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$730
includes taxes & fees
23 Dec - 24 Dec
33 Main
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
2 Bedrooms 1 Bath
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is AU$339
includes taxes & fees
4 Dec - 5 Dec
Tanglewood Suites
Business centre
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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AU$716
includes taxes & fees
18 Dec - 19 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (97)
"Great stay, comfortable place"
United States
barry
The price is AU$224
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AU$284
includes taxes & fees
23 Nov - 24 Nov
The Cornell Inn, Lenox & The Berkshires
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 AU$479
includes taxes & fees
23 Nov - 24 Nov
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
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$511
includes taxes & fees
25 Nov - 26 Nov
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
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$544
includes taxes & fees
23 Nov - 24 Nov
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 AU$575
includes taxes & fees
23 Nov - 24 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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$718
includes taxes & fees
23 Nov - 24 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell 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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"All the design elements are wonderful! I enjoyed the room and the beautiful view of the town and the mountains. So clean and so spacious!! The staff - not so much, but everything else great."
Susie 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Windsor

Windsor B&B information

Number of reviews
2,665
Accommodation
35 B&B
Lowest Price
AU$199
Highest Price
AU$730

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?
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 decor. Chambery Inn: 9 rooms. 17.4 mi (28 km) from the city centre. Enjoy the private garden and snack bar/deli. Whistler's Inn Bed & Breakfast: 14 rooms. 15.8 mi (25.4 km) from the city centre. Enjoy the private garden and unique decor. Lakehouse Inn: 14 rooms. Located 16.8 mi (27 km) from the core of Windsor. Enjoy the free full breakfast and snack bar/deli.
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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