Best Resorts in Windsor

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Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7
In one month
Dec 19 - Dec 21
In two months
Jan 16 - Jan 18

Resorts in Windsor

No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

Lobby sitting area
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$75 nightly
The price is $84
Nov 20 - Nov 21
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Desk, laptop workspace, blackout drapes, iron/ironing board
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, (1004)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
$89 nightly
The price is $100
Nov 20 - Nov 21
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst
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, (959)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$88 nightly
The price is $99
Nov 21 - Nov 22
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (118)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
$122 nightly
The price is $130
Nov 19 - Nov 20
Total with taxes and fees
Blooming Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
$107 nightly
The price is $118
Nov 18 - Nov 19
Total with taxes and fees
Shaker Mill Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Great stay!"
United States
Ann
$99 nightly
The price is $111
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Exterior
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, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$110 nightly
The price is $122
Dec 8 - Dec 9
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 23 - Nov 24
Total with taxes and fees
Element Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (761)
"It's very good for stay over"
United States
Frances
$69 nightly
The price is $77
Dec 1 - Dec 2
Total with taxes and fees
The Villager Motel
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (881)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Nov 18 - Nov 19
Total with taxes and fees
Cozy Corner Motel
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$76 nightly
The price is $85
Dec 5 - Dec 6
Total with taxes and fees
Sunset Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 18 - Nov 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (584)
"Pool, fire pit, grounds and staff were great!"
United States
Kristy
$99 nightly
The price is $111
Nov 18 - Nov 19
Total with taxes and fees
Maple Terrace Motel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
$93 nightly
The price is $104
Dec 7 - Dec 8
Total with taxes and fees
Quality Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
$105 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Smart TV, Netflix, streaming services
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)
"Lovely apartment, perfect for a short getaway for city slickers. Close to town. The apartment was great, came well-equipped and everything was as described. The deck was lovely to spend a slow morning having breakfast. "
United States
Megan N.
$131 nightly
The price is $146
Nov 23 - Nov 24
Total with taxes and fees
In town, newly remodeled studio with private balcony
Single Room | 1 bedroom, in-room safe, desk, free WiFi
Blue Vista Motor Lodge

Blue Vista Motor Lodge

2.0 star property
North Adams
9.8 out of 10, Exceptional, (194)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
$179 nightly
The price is $189
Nov 18 - Nov 19
Total with taxes and fees
Blue Vista Motor Lodge
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1004)
"Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again."
United States
Tammy
$123 nightly
The price is $137
Dec 18 - Dec 19
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (311)
"It was clean and in a convenient location "
United States
Karen
$84 nightly
The price is $94
Nov 23 - Nov 24
Total with taxes and fees
Williamstown Motel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (758)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
$120 nightly
The price is $135
Nov 18 - Nov 19
Total with taxes and fees
Berkshire Mountain Lodge
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 3 days ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Resorts information

Number of reviews
12,391
Accommodation
34 Resorts
Lowest Price
$77
Highest Price
$189

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. Enjoy the sauna, fitness center, and terrace.
What can I do in Windsor?
Wahconah Falls State Park, Crane Museum of Papermaking, 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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