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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

B&B in Windsor

UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
The price is SAR 545
SAR 576 total
includes taxes & fees
5 Nov - 6 Nov
UU Rowe Camp and Conference Center
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (137)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
The price is SAR 652
SAR 728 total
includes taxes & fees
13 Oct - 14 Oct
The Trail in Adams - Berkshires’ Art Hotel
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (428)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is SAR 514
SAR 564 total
includes taxes & fees
4 Nov - 5 Nov
Shaker Mill Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
The price is SAR 680
SAR 797 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"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!! "
The price is SAR 925
SAR 978 total
includes taxes & fees
30 Oct - 31 Oct
Harbour House Inn
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"Very friendly staff. "
The price is SAR 479
SAR 682 total
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
The Red Door B&B
Interior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
The Red Door B&B
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (495)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
The price is SAR 535
SAR 597 total
includes taxes & fees
2 Nov - 3 Nov
Whistler's Inn Bed & Breakfast
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is SAR 1,388
SAR 1,627 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (72)
"The Inn is beautiful. Decor and rooms are well appointed. Breakfast was delicious and served in beautiful rooms. The staff is friendly and welcoming. Our room was on the first floor, and although it was pretty, it was noisy in the morning (starting very early) as it was close to the kitchen/breakfast dining."
The price is SAR 1,845
SAR 2,061 total
includes taxes & fees
10 Nov - 11 Nov
33 Main
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (106)
"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. "
The price is SAR 1,161
SAR 1,404 total
includes taxes & fees
27 Oct - 28 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

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

The price is SAR 778
SAR 1,124 total
includes taxes & fees
28 Oct - 29 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (95)
"Great stay, comfortable place"
The price is SAR 709
SAR 794 total
includes taxes & fees
2 Nov - 3 Nov
Inn at Silver Maple Farm
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is SAR 778
SAR 1,124 total
includes taxes & fees
28 Oct - 29 Oct
Experience Timeless Elegance in The Edith Wharton Room!
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

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

The price is SAR 838
SAR 1,200 total
includes taxes & fees
29 Oct - 30 Oct
Elegant Carriage House room with a queen bed and private patio.
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is SAR 898
SAR 1,275 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is SAR 958
SAR 1,351 total
includes taxes & fees
28 Oct - 29 Oct
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.
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Top Windsor Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Georgecat Front Desk was excellent...professional and helpful."
Stephen 1-night trip
Posted 14 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

Searching for B&Bs in Windsor?
If you want to find an accommodation with fewer rooms than the traditional hotel and a cozy 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 comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.
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 décor. Lakehouse Inn: 14 rooms. 16.8 mi (27 km) from the downtown core. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. 17.4 mi (28 km) from the heart of downtown. Enjoy the private yard and 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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to and around Windsor?
Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the heart of the city. 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.