Search Resort Hotels in Windsor

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Windsor Resorts

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

Recommended hotels in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"Friendly staff and good place for the price. You get everything you need, is clean and close to dinning/shopping. I recommend it. "
The price is CA $148
CA $165 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn PLUS+ South Deerfield – Amherst

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is CA $138
CA $222 total
includes taxes & fees
Aug 28 - Aug 29
Blooming Inn

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (585)
"Amazing place to stay. Can’t wait to go again. "
The price is CA $107
CA $150 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is CA $176
CA $197 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection

In town, newly remodeled studio with private balcony

10.0 out of 10, Exceptional, (114)
"Great place. Quiet, clean and spacious - thank you so much "
The price is CA $131
CA $216 total
includes taxes & fees
Aug 27 - Aug 28
In town, newly remodeled studio with private balcony

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is CA $188
CA $210 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is CA $211
CA $236 total
includes taxes & fees
Sep 1 - Sep 2
Element Lenox Berkshires

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great location!"
The price is CA $200
CA $223 total
includes taxes & fees
Sep 22 - Sep 23
Hotel Downstreet, Ascend Hotel Collection

The Revival House

3.0 star property
9.0 out of 10, Wonderful, (11)
"Self check in was easy. Rooms were spacious and clean. Great place."
The price is CA $250
CA $280 total
includes taxes & fees
Aug 24 - Aug 25
The Revival House

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"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 CA $222
CA $248 total
includes taxes & fees
Aug 26 - Aug 27
Berkshires Untold

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (940)
"Comfortable, clean, and great continental breakfast options! "
The price is CA $123
CA $138 total
includes taxes & fees
Sep 1 - Sep 2
Willows Motel Williamstown

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (729)
"Great quiet stay. "
The price is CA $124
CA $138 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is CA $148
CA $165 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is CA $120
CA $135 total
includes taxes & fees
Sep 7 - Sep 8
Williamstown Motel

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is CA $136
CA $152 total
includes taxes & fees
Sep 1 - Sep 2
Huttopia Berkshires

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is CA $110
CA $123 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (61)
"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "
The price is CA $144
CA $158 total
includes taxes & fees
Sep 1 - Sep 2
The Springs Motel

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Great staff! Comfortable bed! "
The price is CA $200
CA $223 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (410)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is CA $262
CA $323 total
includes taxes & fees
Sep 1 - Sep 2
The Porches Inn at Mass MoCA

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (570)
"Fabulous place"
The price is CA $211
CA $236 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
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

Top Windsor Hotel Reviews