Best Resorts in Windsor

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Recommended hotels in Windsor

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
$107 nightly
The price is $119
Mar 29 - Mar 30
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (880 reviews)
"Beautiful little quaint hotel. I will definitely be returning"
United States
Erin
$78 nightly
The price is $87
Mar 29 - Mar 30
Total with taxes and fees
Berkshires Untold

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$139 nightly
The price is $155
Apr 1 - Apr 2
Total with taxes and fees
Element Lenox Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Cleanliness, staff courtesy, breakfast."
United States
Chris
$84 nightly
The price is $94
Apr 8 - Apr 9
Total with taxes and fees
Quality Inn Lee - Lenox South

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,003 reviews)
"Really nice place staff "
United States
Omayra
$85 nightly
The price is $95
Apr 12 - Apr 13
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
$101 nightly
The price is $111
Apr 1 - Apr 2
Total with taxes and fees
Shaker Mill Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (896 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
$84 nightly
The price is $93
Mar 26 - Mar 27
Total with taxes and fees
Cozy Corner Motel

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
$143 nightly
The price is $154
Mar 26 - Mar 27
Total with taxes and fees
Blooming Inn

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (26 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
$150 nightly
The price is $168
Mar 26 - Mar 27
Total with taxes and fees
The Revival House

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"The frozen heater was extremely loud. Old and tired. Would not recommend however it was very inexpensive so you get what you pay for."
United States
Gary
$72 nightly
The price is $80
Apr 1 - Apr 2
Total with taxes and fees
Rodeway Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
$98 nightly
The price is $110
Mar 26 - Mar 27
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (885 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$108 nightly
The price is $120
Apr 23 - Apr 24
Total with taxes and fees
Berkshire Mountain Lodge

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (783 reviews)
"Very nice motel - well maintained and pleasant management"
United States
Cherie
$75 nightly
The price is $84
Mar 26 - Mar 27
Total with taxes and fees
The Villager Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (599 reviews)
"Very clean room. Service excellent. "
United States
John
$99 nightly
The price is $111
Mar 26 - Mar 27
Total with taxes and fees
Maple Terrace Motel

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$59 nightly
The price is $64
Mar 26 - Mar 27
Total with taxes and fees
Pleasant Valley Motel West Stockbridge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 reviews)
"Amazing stuff they went above and beyond to accommodate on fridge cold day, good breakfast, hot tub is amazing "
United States
Paulo Eduardo
$132 nightly
The price is $147
Mar 29 - Mar 30
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful farm house with goats, ducks, and amazing scenery. Friendly owners, giving duck eggs to take home. Definitely will come back visit for summer and fall. "
United States
Jun X.
$305 nightly
The price is $323
Mar 26 - Mar 27
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (94 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
$109 nightly
The price is $119
Mar 30 - Mar 31
Total with taxes and fees
The Springs Motel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
$96 nightly
The price is $107
Apr 6 - Apr 7
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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
$203 nightly
The price is $214
Mar 29 - Mar 30
Total with taxes and fees
UU Rowe Camp and Conference Center
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

Find out more about Windsor

Windsor Resorts information

Number of reviews
10,113
Accommodation
33 Resorts
Lowest Price
$64
Highest Price
$323

Frequently asked questions

What is Windsor like for a resort vacation?
You deserve a getaway, and a resort is the perfect place to pamper yourself with the amenities and services you need for a relaxing stay in Windsor. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, blissful spa treatments, or nightly entertainment options.
What's a favorite resort for my stay in Windsor?
Our top-rated resorts near Windsor: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Windsor. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - 13 mi (20.9 km) from Windsor. Amenities include a fitness center, an indoor pool, and an outdoor pool. 1 Bd - Vacation Village in the Berkshires - 13.1 mi (21 km) from Windsor. Access to a fitness center.
What can I do in Windsor?
Wahconah Falls State Park, Susan B. Anthony Birthplace Museum, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Swift River and Mount Greylock.
What's the weather like in Windsor?
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's the best way to get to and around Windsor?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the city center. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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