Search Resorts in Windsor

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Sep - 21 Sep
In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Resorts in Windsor

We don't have any properties that match your exact search

Recommended hotels in Windsor

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is SAR 462
SAR 516 total
includes taxes & fees
21 Sep - 22 Sep
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Good location, lovely grounds, we enjoyed the pool"
The price is SAR 469
SAR 524 total
includes taxes & fees
1 Oct - 2 Oct
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (718)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is SAR 475
SAR 531 total
includes taxes & fees
16 Sep - 17 Sep
Berkshires Untold
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is SAR 479
SAR 682 total
includes taxes & fees
14 Sep - 15 Sep
The Cornell Inn, Lenox & The Berkshires
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2004)
"All around loved everything about the place! "
The price is SAR 326
SAR 405 total
includes taxes & fees
21 Sep - 22 Sep
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1001)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is SAR 571
SAR 637 total
includes taxes & fees
15 Sep - 16 Sep
Hotel Downstreet, an Ascend Collection Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (720)
"Pleasant stay"
The price is SAR 436
SAR 539 total
includes taxes & fees
18 Sep - 19 Sep
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (629)
"Nice staff, clean, and lots of apace in the rooms."
The price is SAR 571
SAR 722 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very Good, (541)
"Great place , love it, will return"
The price is SAR 562
SAR 628 total
includes taxes & fees
15 Sep - 16 Sep
The Constance by the Lenox Collection
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (38)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is SAR 531
SAR 593 total
includes taxes & fees
15 Sep - 16 Sep
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Wonderful old inn; chock full of charm."
The price is SAR 721
SAR 973 total
includes taxes & fees
8 Oct - 9 Oct
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (873)
"My usual stop"
The price is SAR 371
SAR 415 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is SAR 368
SAR 411 total
includes taxes & fees
15 Sep - 16 Sep
Huttopia Berkshires
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (770)
"Hotel on North punches above its weight. It's a great hotel in an OK downtown. "
The price is SAR 597
SAR 666 total
includes taxes & fees
28 Sep - 29 Sep
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Very clean rooms and excellent staff."
The price is SAR 399
SAR 445 total
includes taxes & fees
16 Sep - 17 Sep
Best Western Plus Berkshire Hills Inn & Suites
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (294)
"This motel is a good value considering the location and condition. Simple motel that is fairly dated. Very friendly owners/staff. If you are looking for a basic motel that is not expensive, is clean and convenient to Williamstown, this a good fit."
The price is SAR 357
SAR 398 total
includes taxes & fees
14 Sep - 15 Sep
Williamstown Motel
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (877)
"A good location. Easy to find and access. Very clean and modern. "
The price is SAR 413
SAR 461 total
includes taxes & fees
12 Oct - 13 Oct
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (737)
"Perfect location for our passing through vacay."
The price is SAR 334
SAR 373 total
includes taxes & fees
14 Sep - 15 Sep
The Villager Motel
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (779)
"✌"
The price is SAR 267
SAR 298 total
includes taxes & fees
25 Sep - 26 Sep
FairBridge Inn Express
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (631)
"This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area."
The price is SAR 238
SAR 266 total
includes taxes & fees
29 Sep - 30 Sep
Econo Lodge Lee - Great Barrington
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.
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"I visit here vacation village every 2 to 3 months. It's a wonderful experience. Peaceful and safe. Staff are friendly and very helpful. A beautiful outdoor heated swimming pool with Jacuzzi. Its a beautiful Place to visit. I would highly recommend it. "
Claire 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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?
Mount Greylock State Reservation Visitor Center, Mount Greylock, and Barrington Stage Company are a few interesting places to visit nearby. In the area, other attractions include Berkshire Museum and Colonial Theater.
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.