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Top hotels and accommodation in Windsor

The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Beautiful location!"
The price is AU$219
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Loved the Yankee Inn!"
The price is AU$263
includes taxes & fees
17 Aug - 18 Aug
The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1931)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$175
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires
Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (659)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is AU$732
includes taxes & fees
8 Aug - 9 Aug
Berkshires Untold
The Constance by the Lenox Collection
Situated in a tranquil setting, The Whittock offers a traditional home with a covered front porch and mature trees surrounding the property.

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (509)
"Property was excellent "
The price is AU$258
includes taxes & fees
2 Sept - 3 Sept
The Constance by the Lenox Collection
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is AU$281
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Hotel Downstreet, Ascend Hotel Collection
Two single beds with white linens and blue accents, accompanied by bedside tables and lamps, offer a functional workspace.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1006)
"Clean,friendly staff and great location."
The price is AU$248
includes taxes & fees
3 Sept - 4 Sept
Hotel Downstreet, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

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

3.5 star property
9.0 out of 10, Wonderful, (684)
"Had a great time"
The price is AU$227
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (847)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is AU$199
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (761)
"Close to our target event a plus"
The price is AU$123
includes taxes & fees
18 Aug - 19 Aug
FairBridge Inn Express
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Food was great!"
The price is AU$385
includes taxes & fees
14 Aug - 15 Aug
The Red Lion Inn
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (542)
"Excellent stay!"
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Very nice stay"
The price is AU$205
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (619)
"It was a clean, well-run, low cost option. "
The price is AU$110
includes taxes & fees
18 Aug - 19 Aug
Econo Lodge Lee - Great Barrington
Berkshire Travel Lodge
Enjoy a refreshing swim in our pool, surrounded by lush greenery and a serene landscape.

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (431)
"Beautiful scenery. Room was not fancy but comfortable and clean. "
The price is AU$114
includes taxes & fees
6 Aug - 7 Aug
Berkshire Travel Lodge
Howard Johnson by Wyndham Williamstown
Enjoy a refreshing swim in the backyard pool surrounded by a fence.

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (861)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is AU$190
includes taxes & fees
6 Aug - 7 Aug
Howard Johnson by Wyndham Williamstown
Williamstown Motel
Autumnal decorations adorn the grounds, featuring carved pumpkins and seasonal figures.

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (282)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is AU$141
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel
The Villager Motel
Enjoy a serene outdoor setting with a well-maintained lawn and a tall tree, picnic tables, and a playground.

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (725)
"Great quiet stay. "
The price is AU$154
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
Berkshire Valley Inn
Relax in a serene, sheltered space with a cushioned bench and potted plant.

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (554)
"Very clean and very nice staff. Breakfast was great"
The price is AU$287
includes taxes & fees
17 Aug - 18 Aug
Berkshire Valley Inn
Fairfield Inn & Suites by Marriott Williamstown
Experience the Fairfield Inn & Suites' modern design, featuring a prominent brick facade and flat roof.

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (365)
"Great location and breakfast."
The price is AU$309
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites by Marriott Williamstown
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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Learn more about Windsor

Explore Windsor: its dining and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Art displays"
Carolyn 1-night trip
Posted 12 hours ago
Hotel Downstreet, Ascend Hotel Collection

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 Hotel Downstreet, Ascend Hotel Collection and Red Roof Inn PLUS+ South Deerfield – Amherst. See all available top hotels, or vacation rentals in Windsor.

What are some of the best holiday rentals that Windsor has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Windsor offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly. 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 are some hotels with pools in Windsor?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are two additional hotels that feature an on-site pool. View all hotels with pools 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, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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.