Search Windsor hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windsor hotels

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, (1,003 reviews)
"Really nice place staff "
United States
Omayra
The price is AU$134
includes taxes & fees
11 Mar - 12 Mar
Red Roof Inn PLUS+ South Deerfield – Amherst

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is AU$218
includes taxes & fees
9 Mar - 10 Mar
Blooming Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (22 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AU$221
includes taxes & fees
15 Mar - 16 Mar
Element Lenox Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,003 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is AU$134
includes taxes & fees
6 Apr - 7 Apr
Quality Inn Lee - Lenox South

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (868 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is AU$146
includes taxes & fees
5 Apr - 6 Apr
Berkshires Untold

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 AU$178
includes taxes & fees
17 Mar - 18 Mar
Best Western Plus Berkshire Hills Inn & Suites

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (239 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 AU$108
includes taxes & fees
6 Apr - 7 Apr
Rodeway Inn

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (26 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is AU$238
includes taxes & fees
9 Mar - 10 Mar
The Revival House

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AU$91
includes taxes & fees
9 Mar - 10 Mar
Pleasant Valley Motel West Stockbridge

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is AU$151
includes taxes & fees
9 Mar - 10 Mar
Sunset Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is AU$143
includes taxes & fees
29 Mar - 30 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 AU$147
includes taxes & fees
16 Mar - 17 Mar
The Yankee, Trademark Collection by Wyndham

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (895 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is AU$131
includes taxes & fees
15 Mar - 16 Mar
Cozy Corner Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (836 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is AU$126
includes taxes & fees
17 Mar - 18 Mar
Howard Johnson by Wyndham Lenox

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (85 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is AU$210
includes taxes & fees
22 Mar - 23 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (869 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AU$201
includes taxes & fees
5 Apr - 6 Apr
Berkshire Mountain Lodge

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AU$190
includes taxes & fees
22 Mar - 23 Mar
Shaker Mill Inn

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (779 reviews)
"clean modern and spacious room. comfortable king bed. "
United States
William
The price is AU$119
includes taxes & fees
9 Mar - 10 Mar
The Villager Motel

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is AU$338
includes taxes & fees
9 Mar - 10 Mar
UU Rowe Camp and Conference Center

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (596 reviews)
"Cute place"
United States
Lisa
The price is AU$157
includes taxes & fees
9 Mar - 10 Mar
Maple Terrace 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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Recent Reviews in Windsor

More cheap accommodation in Windsor

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Berkshire Mountain Lodge and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
What is staying in Windsor like?
Visitors can enjoy all that Windsor has to offer, including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodation options to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
Places to visit in the wider area include Mount Greylock State Reservation Visitor Center, Swift River and Mount Greylock. You'll also find Berkshire Athenaeum and Berkshire Museum in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia