Windsor Hotels

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Check prices for these dates

Tonight
Jul 7 - Jul 8
Tomorrow
Jul 8 - Jul 9
This weekend
Jul 11 - Jul 13
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Jul 18 - Jul 20

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Top 10 trending Windsor hotels

Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (272)
"a perfecf place to stay as we enjoyed the weekend of fun in the berkshires! the owner was extemely friendly, the room was very clean and comfortable and the location is well located. we would definitely return! "
The price is P6,150
P6,870 total
includes taxes & fees
Jul 9 - Jul 10
Williamstown Motel
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (549)
"Very clean and very nice staff. Breakfast was great"
The price is P8,873
P9,911 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Valley Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Everyone was very nice to us! "
The price is P11,463
P12,804 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn & Suites Berkshires-Lenox
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (48)
"Adorable and immaculately clean. This is a super fun aesthetic place to stay. Add a vending machine or two or better - a lobby attendant that stays til 11 and it'll be perfect!! The pool is iconic. "
The price is P7,333
P8,044 total
includes taxes & fees
Jul 8 - Jul 9
The Springs Motel
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (461)
"Wonderful stay. Helpful, professional staff. "
The price is P13,949
P15,580 total
includes taxes & fees
Jul 9 - Jul 10
The Williams Inn
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is P11,943
P14,600 total
includes taxes & fees
Aug 5 - Aug 6
The Porches Inn at Mass MoCA
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (314)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P11,172
P12,480 total
includes taxes & fees
Jul 15 - Jul 16
The Dewey
Blue Vista Motor Lodge
1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (174)
"Lovely stay!"
The price is P11,866
P12,542 total
includes taxes & fees
Jul 8 - Jul 9
Blue Vista Motor Lodge
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"I had excellent stay at the Red Lion Inn "
The price is P12,357
P16,324 total
includes taxes & fees
Aug 4 - Aug 5
The Red Lion Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Great Place to stay in Small town"
The price is P4,977
P7,760 total
includes taxes & fees
Jul 9 - Jul 10
Blooming Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"Friendly staff, easy parking"
The price is P6,667
P7,447 total
includes taxes & fees
Jul 21 - Jul 22
Quality Inn
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, (1004)
"Fantastic place"
The price is P8,106
P9,054 total
includes taxes & fees
Aug 5 - Aug 6
Hotel Downstreet, Ascend Hotel Collection
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (153)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1857)
"Very nice places "
Vacation Village in the Berkshires
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is P14,801
P15,644 total
includes taxes & fees
Jul 8 - Jul 9
Harbour House Inn
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, (1006)
"Great place to stay "
The price is P6,667
P7,447 total
includes taxes & fees
Jul 13 - Jul 14
Best Western Plus Berkshire Hills Inn & Suites
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (717)
"Great quiet stay. "
The price is P5,586
P6,240 total
includes taxes & fees
Jul 8 - Jul 9
The Villager Motel
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Stayed only one night Very cosy, quiet place "
The price is P10,016
P11,187 total
includes taxes & fees
Jul 9 - Jul 10
The Trail in Adams - Berkshires’ Art Hotel
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, (666)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is P8,916
P10,746 total
includes taxes & fees
Jul 10 - Jul 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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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Frequently asked questions

What's the best place to stay in Windsor?

Hotel Downstreet, Ascend Hotel Collection, located 13.6 mi (21.9 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 Vacation Village in the Berkshires and The Williams Inn. 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 Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Mount Greylock. You'll also find Barrington Stage Company and Berkshire Museum 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.