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Recommended hotels in Windsor

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, (1,009 reviews)
"Clean room, great staff, parking"
United States
Gail
The price is CA $141
CA $157 total
includes taxes & fees
Jul 8 - Jul 9
Red Roof Inn PLUS+ South Deerfield – Amherst

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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is CA $169
CA $189 total
includes taxes & fees
Jun 30 - Jul 1
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is CA $204
CA $228 total
includes taxes & fees
Jul 7 - Jul 8
The Yankee Inn

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (829 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is CA $84
CA $94 total
includes taxes & fees
Jun 29 - Jun 30
FairBridge Inn Express

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is CA $147
CA $234 total
includes taxes & fees
Jun 30 - Jul 1
Blooming Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (866 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is CA $112
CA $125 total
includes taxes & fees
Jul 2 - Jul 3
Berkshire Inn

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is CA $126
CA $189 total
includes taxes & fees
Jun 28 - Jun 29
Becket Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (917 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is CA $125
CA $147 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Corner Motel

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is CA $196
CA $219 total
includes taxes & fees
Jun 29 - Jun 30
Berkshire Lake Lodge

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"Clean room and breakfast"
United States
Raphael
The price is CA $213
CA $301 total
includes taxes & fees
Jul 8 - Jul 9
The Red Lion Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,004 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is CA $204
CA $228 total
includes taxes & fees
Jul 8 - Jul 9
Quality Inn Lee - Lenox South

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (34 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $235
CA $263 total
includes taxes & fees
Jun 29 - Jun 30
The Revival House

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"The property is in terrible condition."
United States
Olga V
The price is CA $107
CA $118 total
includes taxes & fees
Jun 29 - Jun 30
Pleasant Valley Motel West Stockbridge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (113 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is CA $235
CA $262 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $236
CA $259 total
includes taxes & fees
Jul 1 - Jul 2
Shaker Mill Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (999 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is CA $200
CA $255 total
includes taxes & fees
Jul 26 - Jul 27
Berkshire Mountain Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is CA $96
CA $107 total
includes taxes & fees
Jun 29 - Jun 30
Berkshire Travel Lodge

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is CA $155
CA $194 total
includes taxes & fees
Jun 26 - Jun 27
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (669 reviews)
"Decent place.friendly, quiet"
United States
William
The price is CA $132
CA $147 total
includes taxes & fees
Jul 12 - Jul 13
Econo Lodge Lee - Great Barrington

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (327 reviews)
"Clean rooms and the staff was extremely friendly and helpful"
United States
Graham
The price is CA $141
CA $157 total
includes taxes & fees
Jul 6 - Jul 7
Williamstown Motel
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Top Windsor Hotel Reviews

Find out more about Windsor

Windsor Resorts information

Number of reviews
11,915
Accommodation
30 Resorts
Lowest Price
CA $94
Highest Price
CA $301

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?
Here's our top-rated resort near Windsor: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 19.9 mi (32 km) from Windsor. Has a sauna, a fitness center, and a terrace.
What can I do in Windsor?
Susan B. Anthony Birthplace Museum, Berkshire Scenic Railway Museum, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Skyline Trail and Swift River.
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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