Search Windsor Bed & Breakfast

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Windsor bed & breakfast

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (443 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is AU$169
includes taxes & fees
28 Jan - 29 Jan
Shaker Mill Inn

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.
The price is AU$228
includes taxes & fees
31 Jan - 1 Feb
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
The price is AU$235
includes taxes & fees
24 Jan - 25 Jan
UU Rowe Camp and Conference Center

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AU$227
includes taxes & fees
29 Jan - 30 Jan
Lakehouse Inn

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
The price is AU$289
includes taxes & fees
21 Jan - 22 Jan
The Trail in Adams - Berkshires’ Art Hotel

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 AU$339
includes taxes & fees
27 Jan - 28 Jan
Harbour House Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (99 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is AU$215
includes taxes & fees
22 Jan - 23 Jan
Inn at Silver Maple Farm

Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is AU$206
includes taxes & fees
31 Jan - 1 Feb
Cozy Farmhouse Retreat - Ram Dass Room

Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is AU$228
includes taxes & fees
31 Jan - 1 Feb
Cozy Retreat in historic Farmhouse - Tranquility 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
The price is AU$558
includes taxes & fees
15 Feb - 16 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 AU$699
includes taxes & fees
22 Jan - 23 Jan
33 Main

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
The price is AU$940
includes taxes & fees
24 Jan - 25 Jan
Inn at Kenmore Hall

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$482
includes taxes & fees
1 Feb - 2 Feb
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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
The price is AU$267
includes taxes & fees
1 Feb - 2 Feb
The Cornell Inn, Lenox & The Berkshires

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$482
includes taxes & fees
1 Feb - 2 Feb
Experience Timeless Elegance in The Edith Wharton Room!

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$514
includes taxes & fees
1 Feb - 2 Feb
Elegant Carriage House room with a queen bed and private patio.

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
1 Feb - 2 Feb
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$576
includes taxes & fees
1 Feb - 2 Feb
Historic Susan B. Anthony Room - Cozy & Charming Stay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

Windsor B&B information

Number of reviews
2,232
Accommodation
35 B&B
Lowest Price
AU$169
Highest Price
AU$940

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. Brook Farm Inn: 15 rooms. 16.5 mi (26.5 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Chambery Inn: 9 rooms. Situated 17.4 mi (28 km) from the heart of Windsor. Enjoy the private garden and snack bar/deli. 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.

Explore a world of travel with Expedia