Search Resort Hotels in Windsor from CA $91

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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $150
CA $168 total
includes taxes & fees
May 12 - May 13
Best Western Plus Berkshire Hills Inn & Suites
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, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is CA $135
CA $151 total
includes taxes & fees
May 18 - May 19
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is CA $142
CA $155 total
includes taxes & fees
May 11 - May 12
Shaker Mill Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (904 reviews)
"Everything was clean and very comfortable. The room was quite spacious and the bathroom brand new and very clean! From parking to friendliness to safety my stay was top notch! "
United States
Heidi
The price is CA $108
CA $128 total
includes taxes & fees
May 17 - May 18
Cozy Corner Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is CA $155
CA $173 total
includes taxes & fees
May 14 - May 15
Berkshires Untold
Lobby

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)
"Great location "
United States
Edith
The price is CA $159
CA $177 total
includes taxes & fees
May 27 - May 28
Quality Inn Lee - Lenox South
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (135 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
The price is CA $138
CA $221 total
includes taxes & fees
May 27 - May 28
Blooming Inn
Reception

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, (1,007 reviews)
"Was great room was clean staff was nice"
United States
Theresa
The price is CA $146
CA $164 total
includes taxes & fees
May 17 - May 18
Red Roof Inn PLUS+ South Deerfield – Amherst
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (926 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is CA $120
CA $165 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $236
CA $264 total
includes taxes & fees
May 12 - May 13
The Revival House
Property grounds

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (122 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is CA $157
CA $244 total
includes taxes & fees
Jun 4 - Jun 5
In town, newly remodeled studio with private balcony
Standard Room, 1 King Bed, Non Smoking

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (242 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is CA $97
CA $109 total
includes taxes & fees
May 17 - May 18
Rodeway Inn
Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,003 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $83
CA $91 total
includes taxes & fees
May 26 - May 27
Pleasant Valley Motel West Stockbridge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is CA $108
CA $121 total
includes taxes & fees
May 11 - May 12
The Villager Motel
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $228
CA $255 total
includes taxes & fees
May 17 - May 18
Element Lenox Berkshires
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (602 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is CA $149
CA $167 total
includes taxes & fees
May 13 - May 14
Maple Terrace Motel
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, (853 reviews)
"Great value"
United States
Ralph
The price is CA $108
CA $121 total
includes taxes & fees
May 11 - May 12
Howard Johnson by Wyndham Lenox
Indoor pool

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, (93 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is CA $161
CA $180 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Staff was friendly, room was clean and the beds were comfortable. Dog friendly also. Good breakfast selection. I would stay there again."
United States
Lillian
The price is CA $173
CA $193 total
includes taxes & fees
May 19 - May 20
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (96 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
The price is CA $155
CA $171 total
includes taxes & fees
May 11 - May 12
The Springs Motel
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Pleasant staff all around, quick to accomodate needs. Rooms, hallways, public areas, grounds, all very clean. Price was the best in the area. "
Vincent 4-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

Find out more about Windsor

Windsor Resorts information

Number of reviews
11,845
Accommodation
28 Resorts
Lowest Price
CA $91
Highest Price
CA $264

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 resort near Windsor: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 19.9 mi (32 km) from Windsor. Access to a sauna, a fitness center, and a terrace.
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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