Search Resort Hotels in Windsor from CA $105

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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, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is CA $124
CA $138 total
includes taxes & fees
Feb 9 - Feb 10
Best Western Plus Berkshire Hills Inn & Suites

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)
"Really nice place staff "
United States
Omayra
The price is CA $122
CA $136 total
includes taxes & fees
Mar 5 - Mar 6
Red Roof Inn PLUS+ South Deerfield – Amherst

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, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is CA $140
CA $156 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is CA $123
CA $204 total
includes taxes & fees
Feb 8 - Feb 9
Blooming Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is CA $134
CA $150 total
includes taxes & fees
Feb 8 - Feb 9
The Yankee, Trademark Collection by Wyndham

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.6 out of 10, Good, (235 reviews)
"The room was clean and nice but i was confusing about the abandoned vehicles directly behind the hotel."
United States
Anonymous traveller
The price is CA $104
CA $116 total
includes taxes & fees
Mar 8 - Mar 9
Rodeway Inn

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, (1,001 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is CA $134
CA $149 total
includes taxes & fees
Mar 1 - Mar 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is CA $191
CA $213 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is CA $150
CA $165 total
includes taxes & fees
Feb 8 - Feb 9
Shaker Mill Inn

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)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is CA $115
CA $129 total
includes taxes & fees
Feb 24 - Feb 25
Quality Inn Lee - Lenox South

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is CA $188
CA $210 total
includes taxes & fees
Feb 27 - Feb 28
Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (830 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is CA $94
CA $105 total
includes taxes & fees
Feb 8 - Feb 9
Howard Johnson by Wyndham Lenox

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,004 reviews)
"Very clean and warm room, kind staff, many fresh fruits for breakfast. Wonderful stay in cold January."
United States
ALEXEI
The price is CA $105
CA $117 total
includes taxes & fees
Feb 8 - Feb 9
Willows Motel Williamstown

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is CA $204
CA $290 total
includes taxes & fees
Mar 10 - Mar 11
The Red Lion Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (852 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is CA $121
CA $135 total
includes taxes & fees
Mar 8 - Mar 9
Berkshires Untold

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,001 reviews)
"Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel."
United States
Kelly
The price is CA $172
CA $192 total
includes taxes & fees
Mar 4 - Mar 5
Hotel Downstreet, an Ascend Collection Hotel

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The room and amenities were amazing. "
United States
Kathleen
The price is CA $163
CA $182 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn & Suites Berkshires-Lenox

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (894 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is CA $102
CA $121 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Corner Motel

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (119 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is CA $117
CA $200 total
includes taxes & fees
Mar 2 - Mar 3
In town, newly remodeled studio with private balcony

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (832 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is CA $154
CA $199 total
includes taxes & fees
Feb 9 - Feb 10
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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Top Windsor Hotel Reviews

Find out more about Windsor

Windsor Resorts information

Number of reviews
14,769
Accommodation
33 Resorts
Lowest Price
CA $105
Highest Price
CA $290

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. Vacation Village In The Berkshires 5 Star Resort - Suite B - Family-friendly resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Amenities include a fitness center, a car charging station, and a garden. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.8 mi (20.7 km) from Windsor. Access to ski-in/ski-out access, a sauna, and a fitness center.
What can I do in Windsor?
Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Mount Greylock are a few interesting places to visit nearby. In the area, other attractions include Berkshire Athenaeum and Berkshire Museum.
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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