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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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

Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (399)
"Emma & staff were very friendly Emma was especially helpful as we booked 2 rooms in error for this same stay. Maid service was awesome and we appreciated the water coffee & tea as well as bagels etc. Enjoyed the Fireplace only want was a hot tub that would have made it the much more enjoyable apres ski "
The price is SAR 435
SAR 528 total
includes taxes & fees
3 Mar - 4 Mar
Mountaineer Inn
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (486)
"Rooms were very clean. Entire place smelled amazing. Very comfortable! "
The price is SAR 363
SAR 406 total
includes taxes & fees
13 Feb - 14 Feb
Life House Berkshires
D. Hotel Suites & Spa
Front of property

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2347)
"Staff"
The price is SAR 485
SAR 563 total
includes taxes & fees
2 Feb - 3 Feb
D. Hotel Suites & Spa
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (178)
"Older, air drying in the locker rooms odd . Moisture. "
The price is SAR 1,103
SAR 1,320 total
includes taxes & fees
3 Mar - 4 Mar
Mount Snow Grand Summit Resort
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (407)
"Very modern good restaurant convienent"
The price is SAR 703
SAR 786 total
includes taxes & fees
2 Feb - 3 Feb
The Williams Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (592)
"Plenty of room. Good location to local skiing. Clean."
The price is SAR 446
SAR 551 total
includes taxes & fees
3 Mar - 4 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1003)
"Easy to get to, nice location "
The price is SAR 435
SAR 486 total
includes taxes & fees
17 Feb - 18 Feb
Hotel Downstreet, Ascend Hotel Collection
Tru by Hilton Chicopee Springfield
Exterior

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1002)
"Our room was very clean. The breakfast was good with good assortment of choices. The lobby was a good place to hang out and have a cup of tea and work. My only complaint is the pool water was cloudy and had a strong smell of chloramines. They need to work out the chemical balance and do daily checks. Other wise it was a pleasant stay."
The price is SAR 379
SAR 430 total
includes taxes & fees
5 Feb - 6 Feb
Tru by Hilton Chicopee Springfield
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again. "
The price is SAR 368
SAR 411 total
includes taxes & fees
2 Feb - 3 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"The property is historic, so the lodgings are dated along with some of the amenities. I only stayed one night and most likely would have stayed somewhere more modern if it was longer."
The price is SAR 506
SAR 733 total
includes taxes & fees
5 Feb - 6 Feb
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (729)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is SAR 398
SAR 444 total
includes taxes & fees
7 Feb - 8 Feb
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Big Bears Lodge
Front of property

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (167)
"Great place had to leave my stuff in the ski room to dry off. For a bit after checkout. They we're very accommodating "
The price is SAR 625
SAR 688 total
includes taxes & fees
2 Feb - 3 Feb
Big Bears Lodge
Chalet 239
Room

Chalet 239

2.0 star property
9.4 out of 10, Exceptional, (56)
"Place is very new. House keeper should give little details to the inside refrigerator. Little filthy "
The price is SAR 695
SAR 764 total
includes taxes & fees
23 Feb - 24 Feb
Chalet 239
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Comfortable room. Very clean "
The price is SAR 385
SAR 430 total
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (680)
"Had a great stay - such a gem of a hotel. "
The price is SAR 428
SAR 478 total
includes taxes & fees
9 Feb - 10 Feb
Hotel On North
Red Roof Inn PLUS+ West Springfield
Exterior

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1003)
"Thank you so much !!"
The price is SAR 317
SAR 363 total
includes taxes & fees
3 Mar - 4 Mar
Red Roof Inn PLUS+ West Springfield
The Ellery
Exterior

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (587)
"The room was cosy and clean. The receptionist was welcoming and treated us with an unsolicited upgrade!"
The price is SAR 521
SAR 582 total
includes taxes & fees
2 Feb - 3 Feb
The Ellery
Motel 6 Chicopee, MA - Springfield
Exterior

Motel 6 Chicopee, MA - Springfield

2.0 star property
6.4 out of 10, (1000)
"It is a very nice property I will stay again"
The price is SAR 284
SAR 329 total
includes taxes & fees
2 Feb - 3 Feb
Motel 6 Chicopee, MA - Springfield
Homewood Suites by Hilton Holyoke-Springfield/North
Terrace/patio

Homewood Suites by Hilton Holyoke-Springfield/North

3.0 star property
9.0 out of 10, Wonderful, (948)
"Our stay was good. Hotel was clean and comfortable. It does need some updating but in general was good. The pictures of the suites do not match what you get. The shower is not handicap accessible for wheelchair bond guests."
The price is SAR 475
SAR 531 total
includes taxes & fees
6 Feb - 7 Feb
Homewood Suites by Hilton Holyoke-Springfield/North
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (425)
"It is a 3 day family trip. Our stay was excellent. Room is big and tidy. The staff was very nice and accomodating.. the place is close to all.. restaurant, grocery, gas station etc.. "
The price is SAR 409
SAR 532 total
includes taxes & fees
2 Feb - 3 Feb
Berkshire Mountain Lodge
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, (1759)
"Great place "
The price is SAR 563
SAR 655 total
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 867
SAR 969 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (924)
"Staff was exceptionally helpful and friendly."
The price is SAR 709
SAR 778 total
includes taxes & fees
2 Feb - 3 Feb
Jiminy Peak Mountain Resort
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. Situated 17.4 mi (28 km) from the heart of Windsor. Enjoy the private yard and deli. 33 Main: 8 rooms. Located 16.1 mi (25.8 km) from the core of Windsor. Enjoy the free full breakfast and unique décor.
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.