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Compare 980 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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, (1000)
"Beautiful location!"
The price is NT$3,795
NT$4,239 total
includes taxes & fees
Sep 1 - Sep 2
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, (1000)
"Wonderful place to stay"
The price is NT$4,288
NT$4,789 total
includes taxes & fees
Sep 1 - Sep 2
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, (1935)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is NT$3,245
NT$3,954 total
includes taxes & fees
Aug 27 - Aug 28
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, (663)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NT$4,813
NT$5,376 total
includes taxes & fees
Sep 1 - Sep 2
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 NT$4,521
NT$5,050 total
includes taxes & fees
Sep 2 - Sep 3
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, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is NT$3,826
NT$5,445 total
includes taxes & fees
Sep 1 - Sep 2
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, (1000)
"Clean,friendly staff and great location."
The price is NT$4,304
NT$4,808 total
includes taxes & fees
Sep 7 - Sep 8
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, (686)
"Had a great time"
The price is NT$3,035
NT$3,808 total
includes taxes & fees
Sep 2 - Sep 3
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, (852)
"Consistently a clean room with welcoming staff."
The price is NT$3,446
NT$3,849 total
includes taxes & fees
Sep 1 - Sep 2
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, (763)
"Close to our target event a plus"
The price is NT$2,128
NT$2,377 total
includes taxes & fees
Aug 20 - Aug 21
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, (1000)
"Loved our visit"
The price is NT$5,663
NT$7,664 total
includes taxes & fees
Aug 27 - Aug 28
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, (546)
"Excellent stay!"
Berkshire Mountain Lodge
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, (621)
"It was lovely!"
The price is NT$1,908
NT$2,131 total
includes taxes & fees
Aug 20 - Aug 21
Econo Lodge Lee - Great Barrington
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, (1004)
"Very nice stay"
The price is NT$3,565
NT$3,982 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
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 NT$2,235
NT$2,414 total
includes taxes & fees
Aug 20 - Aug 21
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, (862)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is NT$3,291
NT$3,676 total
includes taxes & fees
Aug 19 - Aug 20
Howard Johnson by Wyndham Williamstown
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 NT$2,667
NT$2,979 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel
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 NT$2,670
NT$2,982 total
includes taxes & fees
Sep 2 - Sep 3
Williamstown 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 NT$4,982
NT$5,565 total
includes taxes & fees
Aug 19 - Aug 20
Berkshire Valley Inn
Red Roof Inn PLUS+ South Deerfield – Amherst
Relax in this inviting space with a large bed, desk, and TV, surrounded by a window and decorative touches.

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1004)
"Quiet and nice stay. Wish the area had better bus service ."
The price is NT$3,209
NT$3,584 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn PLUS+ South Deerfield – Amherst
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 food and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 20 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 traveler data. Other good options for your visit to the area are Berkshire Mountain Lodge and FairBridge Inn Express. See all available top hotels, or vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

Where can I learn more about changing or cancelling my trip to Windsor?

For more information about updating your trip to Windsor or cancelling it, click here.

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 with an onsite pool. View all hotels with pools in Windsor.

What's the best hotel for staying near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations 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. Check out what more to see and do in Expedia's Windsor guide.

What's the seasonal 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.