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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 May - 3 May
In two weeks
8 May - 10 May
In one month
22 May - 24 May
In two months
19 June - 21 June

Our top choices for Windsor bed & breakfast

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
The price is AU$298
includes taxes & fees
22 Apr - 23 Apr
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, (146 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
The price is AU$270
includes taxes & fees
3 May - 4 May
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)
"Nice place for a weekend away."
United States
Gregory
The price is AU$343
includes taxes & fees
27 Apr - 28 Apr
Harbour House Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AU$266
includes taxes & fees
23 Apr - 24 Apr
Chambery Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is AU$465
includes taxes & fees
27 Apr - 28 Apr
Devonfield Inn B&B
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
The price is AU$429
includes taxes & fees
4 May - 5 May
The Inn at Stockbridge
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AU$354
includes taxes & fees
10 May - 11 May
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 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$816
includes taxes & fees
27 Apr - 28 Apr
33 Main
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$386
includes taxes & fees
3 May - 4 May
Experience Timeless Elegance in The Edith Wharton Room!
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is AU$162
includes taxes & fees
5 May - 6 May
Shaker Mill Inn
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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AU$521
includes taxes & fees
4 May - 5 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Interior

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$466
includes taxes & fees
3 May - 4 May
Elegant Carriage House room with a queen bed and private patio.
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is AU$207
includes taxes & fees
4 May - 5 May
The Cornell Inn, Lenox & The Berkshires
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$386
includes taxes & fees
3 May - 4 May
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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$494
includes taxes & fees
3 May - 4 May
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$523
includes taxes & fees
3 May - 4 May
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, bed sheets

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$651
includes taxes & fees
3 May - 4 May
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AU$691
includes taxes & fees
4 May - 5 May
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace

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$794
includes taxes & fees
3 May - 4 May
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AU$794
includes taxes & fees
3 May - 4 May
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"The kitchen was fully equipped, the staff was wonderful and there is plenty of active"
Kathleen 2-night trip
Posted less than an hour ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Windsor

Windsor B&B information

Number of reviews
1,886
Accommodation
45 B&B
Lowest Price
AU$162
Highest Price
AU$816

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. Lakehouse Inn: 14 rooms. 16.8 mi (27 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 8.6 mi (13.9 km) from the city centre. Enjoy the unique decor and arcade/games room. Chambery Inn: 9 rooms. Located 17.4 mi (28 km) from the core of Windsor. Enjoy the private garden 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