Best Resorts in Windsor

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Feb 20 - Feb 22
In two weeks
Feb 27 - Mar 1
In one month
Mar 13 - Mar 15
In two months
Apr 10 - Apr 12
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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
$98 nightly
The price is $109
Feb 22 - Feb 23
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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)
"Really nice place staff "
United States
Omayra
$89 nightly
The price is $100
Mar 1 - Mar 2
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, (1,004 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
$102 nightly
The price is $114
Mar 7 - Mar 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
$93 nightly
The price is $103
Feb 22 - Feb 23
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Front of property

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
$139 nightly
The price is $150
Mar 3 - Mar 4
Total with taxes and fees
Blooming Inn
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, (1,004 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$98 nightly
The price is $109
Mar 2 - Mar 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
$84 nightly
The price is $94
Feb 23 - Feb 24
Total with taxes and fees
Quality Inn Lee - Lenox South
Lobby lounge

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
$139 nightly
The price is $155
Feb 22 - Feb 23
Total with taxes and fees
Element Lenox Berkshires
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, (830 reviews)
"Staff was very friendly and helpful."
United States
Pamela
$69 nightly
The price is $77
Feb 10 - Feb 11
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.6 out of 10, Good, (236 reviews)
"The room was clean and nice but i was confusing about the abandoned vehicles directly behind the hotel."
United States
Anonymous traveler
$76 nightly
The price is $85
Mar 11 - Mar 12
Total with taxes and fees
Rodeway Inn
Property amenity

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, (833 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
$130 nightly
The price is $145
Feb 22 - Feb 23
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Garden

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
$112 nightly
The price is $123
Feb 10 - Feb 11
Total with taxes and fees
Shaker Mill Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (854 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
$98 nightly
The price is $110
Mar 8 - Mar 9
Total with taxes and fees
Berkshires Untold
Lobby lounge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The room and amenities were amazing. "
United States
Kathleen
$119 nightly
The price is $133
Mar 1 - Mar 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
$185 nightly
The price is $207
Mar 10 - Mar 11
Total with taxes and fees
The Red Lion Inn
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (200 reviews)
"Great stay! "
United States
ALEKSey
$179 nightly
The price is $189
Feb 10 - Feb 11
Total with taxes and fees
Blue Vista Motor Lodge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (773 reviews)
"clean modern and spacious room. comfortable king bed. "
United States
William
$75 nightly
The price is $84
Feb 10 - Feb 11
Total with taxes and fees
The Villager Motel
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
$148 nightly
The price is $165
Feb 15 - Feb 16
Total with taxes and fees
Lakehouse Inn
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, (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
$126 nightly
The price is $140
Feb 24 - Feb 25
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, (894 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
$79 nightly
The price is $88
Feb 16 - Feb 17
Total with taxes and fees
Cozy Corner 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The staff was wonderful "
Linda 2-night trip
Posted 13 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Windsor

Windsor Resorts information

Number of reviews
14,259
Accommodation
33 Resorts
Lowest Price
$77
Highest Price
$207

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.

Explore a world of travel with Expedia