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Compare 26 B&B in Windsor with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great place "
The price is SAR 458
SAR 537 total
includes taxes & fees
30 Dec - 31 Dec
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"This is the most pleasant and comfortable experience I’ve ever had in any hotel. The staff and amenities were outstanding. "
The price is SAR 473
SAR 555 total
includes taxes & fees
30 Dec - 31 Dec
Lakehouse Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is SAR 713
SAR 797 total
includes taxes & fees
30 Dec - 31 Dec
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is SAR 394
SAR 433 total
includes taxes & fees
5 Jan - 6 January 2025
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
9.8 out of 10, Exceptional, (120)
"Great location "
The price is SAR 1,085
SAR 1,212 total
includes taxes & fees
10 Jan - 11 January 2025
Devonfield Inn B&B
33 Main
Room

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is SAR 1,367
SAR 1,527 total
includes taxes & fees
20 Jan - 21 January 2025
33 Main
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is SAR 560
SAR 604 total
includes taxes & fees
5 Jan - 6 January 2025
Inn at Silver Maple Farm
Tanglewood Suites
Property grounds

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 822
SAR 822 total
includes taxes & fees
31 Dec - 1 January 2025
Tanglewood Suites
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, (125)
"Stayed only one night Very cosy, quiet place "
The price is SAR 606
SAR 676 total
includes taxes & fees
2 Jan - 3 January 2025
The Trail in Adams - Berkshires’ Art Hotel
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is SAR 687
SAR 768 total
includes taxes & fees
3 Jan - 4 January 2025
Brook Farm Inn
Whistler's Inn Bed & Breakfast
Interior

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,594
SAR 1,928 total
includes taxes & fees
1 Jan - 2 January 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Room

Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible

9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is SAR 3,755
SAR 4,790 total
includes taxes & fees
30 Dec - 31 Dec
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Bathroom

Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is SAR 3,755
SAR 4,790 total
includes taxes & fees
30 Dec - 31 Dec
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Inn at Kenmore Hall
Front of property

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is SAR 1,596
SAR 1,751 total
includes taxes & fees
3 Jan - 4 January 2025
Inn at Kenmore Hall
Harbour House Inn
Room

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 965
SAR 1,020 total
includes taxes & fees
1 Jan - 2 January 2025
Harbour House Inn
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Room

Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is SAR 3,755
SAR 4,790 total
includes taxes & fees
3 Jan - 4 January 2025
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Eastgate Inn B&B
Front of property

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Interior

Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite

10.0 out of 10, Exceptional, (6)
The price is SAR 3,755
SAR 4,790 total
includes taxes & fees
31 Dec - 1 January 2025
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
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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Other property types in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (921)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 710
SAR 779 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
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.

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: 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.
What is there to do in Windsor?
Spend some time exploring Savoy Mountain State Forest and Mohawk Trail State Forest if you’re hoping to see some of the area’s natural features. You might put Berkshire East Ski Resort and Jiminy Peak Mountain Resort on your list if you want to see more of the area.
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.