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Aug 20 - Aug 21
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Aug 21 - Aug 22
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Aug 22 - Aug 24
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Top 10 trending Windsor hotels

Our top choices for Windsor hotels

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Wonderful place to stay"
The price is P7,643
P8,537 total
includes taxes & fees
Sep 18 - Sep 19
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is P7,233
P8,080 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (687)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is P9,131
P10,199 total
includes taxes & fees
Aug 26 - Aug 27
Berkshires Untold
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1959)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is P6,174
P7,521 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great location!"
The price is P8,669
P9,683 total
includes taxes & fees
Aug 24 - Aug 25
Hotel Downstreet, Ascend Hotel Collection
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, (1000)
"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 P7,277
P10,357 total
includes taxes & fees
Sep 2 - Sep 3
The Cornell Inn, Lenox & The Berkshires
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (523)
"Great place , love it, will return"
The price is P8,524
P9,521 total
includes taxes & fees
Sep 15 - Sep 16
The Constance by the Lenox Collection
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (581)
"Amazing place to stay. Can’t wait to go again. "
The price is P3,758
P5,473 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1008)
"Loved our visit"
The price is P10,795
P14,609 total
includes taxes & fees
Aug 26 - Aug 27
The Red Lion Inn
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, (697)
"Pleasant stay"
The price is P5,227
P6,636 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is P4,052
P4,527 total
includes taxes & fees
Sep 2 - Sep 3
FairBridge Inn Express
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, (863)
"Consistently a clean room with welcoming staff."
The price is P6,555
P7,321 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (19)
"Really enjoyed my stay here, definitely need a car to get around"
The price is P7,703
P8,604 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (867)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is P5,711
P6,379 total
includes taxes & fees
Aug 21 - Aug 22
Howard Johnson by Wyndham Williamstown
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (435)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is P3,847
P4,308 total
includes taxes & fees
Aug 27 - Aug 28
Berkshire Travel Lodge
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (728)
"Great quiet stay. "
The price is P5,083
P5,678 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (625)
"It was lovely!"
The price is P3,641
P4,067 total
includes taxes & fees
Sep 3 - Sep 4
Econo Lodge Lee - Great Barrington
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (289)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is P5,078
P5,673 total
includes taxes & fees
Sep 2 - Sep 3
Williamstown Motel
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 P6,055
P6,764 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (756)
"Staff were excellent and welcoming."
The price is P10,202
P11,396 total
includes taxes & fees
Sep 8 - Sep 9
Hotel On North
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

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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

10/10 Excellent
"None "
Maurice 2-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, 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 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'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.