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Best Resorts in Windsor

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Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
$169 nightly
The price is $189
Jul 22 - Jul 23
Total with taxes and fees
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

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)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
$118 nightly
The price is $132
Jul 26 - Jul 27
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (36 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
$149 nightly
The price is $166
Jul 21 - Jul 22
Total with taxes and fees
The Revival House
Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (857 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$63 nightly
The price is $70
Jul 27 - Jul 28
Total with taxes and fees
FairBridge Inn Express
Property grounds

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
$129 nightly
The price is $136
Jul 22 - Jul 23
Total with taxes and fees
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Property grounds

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
10.0 out of 10, Exceptional, (2 reviews)
"The room was clean and well appointed with ample bedding, towels, electrical outlets and fans (it was a very hot weekend). The house is spacious and the bathroom was well equipped. The host was very responsive to a question about off hours arrival. HIghly recommend."
United States
Mary M.
$129 nightly
The price is $136
Jul 22 - Jul 23
Total with taxes and fees
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,004 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"
United States
Margaret
$130 nightly
The price is $145
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

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, (137 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$145 nightly
The price is $162
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, WiFi (free), bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (258 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
$86 nightly
The price is $96
Jul 27 - Jul 28
Total with taxes and fees
Rodeway Inn
Desk, iron/ironing board, WiFi (free), bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (885 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
$90 nightly
The price is $101
Jul 21 - Jul 22
Total with taxes and fees
Berkshire Inn
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
$231 nightly
The price is $244
Aug 12 - Aug 13
Total with taxes and fees
Harbour House Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (885 reviews)
"Great place"
United States
Luciane
$99 nightly
The price is $111
Jul 21 - Jul 22
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
$201 nightly
The price is $225
Jul 21 - Jul 22
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (108 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
$127 nightly
The price is $139
Jul 21 - Jul 22
Total with taxes and fees
The Springs Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
"Great location too"
United States
judith
$155 nightly
The price is $173
Aug 19 - Aug 20
Total with taxes and fees
Berkshire Mountain Lodge
Front of property

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Quick check in and comfortable bed in a pretty New England town."
United States
William
$161 nightly
The price is $179
Aug 16 - Aug 17
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (932 reviews)
"Loved this place"
United States
Jeremy
$100 nightly
The price is $111
Jul 22 - Jul 23
Total with taxes and fees
Cozy Corner Motel
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (379 reviews)
"Central location!"
United States
Brenda
$96 nightly
The price is $108
Jul 22 - Jul 23
Total with taxes and fees
The Central Downtown Inn & Suites
Lobby

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)
"Great place"
United States
Michelle
$135 nightly
The price is $151
Aug 10 - Aug 11
Total with taxes and fees
Quality Inn Lee - Lenox South
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
"Great value and excellent location"
United States
Truett
$89 nightly
The price is $99
Jul 21 - Jul 22
Total with taxes and fees
Willows Motel Williamstown
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

Berkshires Untold

Berkshires Untold

8/10 Good
"Its an interesting experience in that we thought we were staying at a hotel/ inn. The pictures and the website lead one to believe that but when we got there, we saw a motel. Nothing wrong with that but we felt we had been misinformed. They push the pcitures of the Club room which looks like an inn/ restaurant but that is the front of the building but attached to it is the motel where you stay. Again, once we knew that, we were fine but honestly, we were looking for more of an Inn or a hotel/ inn. It comes over as a glorified motel. The staff is wonderful and the Club room is a nice addition but I really thought the advertising was duplicitous. We were talking to a friend about it and she agreed that she also felt misled. I'm not sure that they have to do this but I guess if you put motel, you wouldn't get as much interest nor could you charge the same? Other than that, no comment."
Margaret 1-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Windsor

Windsor Resorts information

Number of reviews
11,529
Accommodation
28 Resorts
Lowest Price
$70
Highest Price
$225

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, Mount Greylock State Reservation Visitor Center, and Skyline Trail 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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