Windsor Hotels

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Jul 1 - Jul 2
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Jul 4 - Jul 6
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Jul 11 - Jul 13

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Top 10 trending Windsor hotels

Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (562)
"Good place to spend one night. Helpful and kind staff "
The price is P7,831
P8,747 total
includes taxes & fees
Jul 8 - Jul 9
Maple Terrace 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 P8,811
P9,842 total
includes taxes & fees
Jul 8 - Jul 9
Berkshire Valley Inn
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 P12,782
P16,804 total
includes taxes & fees
Jul 14 - Jul 15
The Red Lion Inn
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (827)
"This is a hidden gem. Owners we so nice and the property was well taken care of, along with newly updated fixtures. "
The price is P5,521
P6,473 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Corner Motel
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, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P8,770
P11,999 total
includes taxes & fees
Jul 6 - Jul 7
The Cornell Inn, Lenox & The Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Nice place to stay. Good breakfast. "
The price is P8,093
P9,039 total
includes taxes & fees
Jul 9 - Jul 10
The Yankee, Trademark Collection by Wyndham
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (392)
"Perfect for our needs"
The price is P12,165
P14,852 total
includes taxes & fees
Jul 13 - Jul 14
The Porches Inn at Mass MoCA
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, (1005)
"Very cute hotel. The room was huge and the staff were friendly. "
The price is P8,569
P9,571 total
includes taxes & fees
Jul 20 - Jul 21
Hotel Downstreet, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great place"
The price is P15,779
P17,626 total
includes taxes & fees
Jul 6 - Jul 7
The Black Swan Lee - Lenox, Ascend Hotel Collection
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1003)
"Friendly staff, easy parking"
The price is P6,656
P7,435 total
includes taxes & fees
Jul 21 - Jul 22
Quality Inn
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (923)
"Clean, conscientious service, great breakast spread. "
The price is P4,530
P5,061 total
includes taxes & fees
Jul 2 - Jul 3
Willows Motel Williamstown
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
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, (172)
"Lovely stay!"
The price is P11,252
P11,893 total
includes taxes & fees
Jul 2 - Jul 3
Blue Vista Motor Lodge
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (366)
"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
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P12,656
P14,137 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Lenox Pittsfield
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (458)
"Wonderful stay. Helpful, professional staff. "
The price is P13,981
P15,617 total
includes taxes & fees
Jul 9 - Jul 10
The Williams Inn
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (271)
"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 P6,704
P7,488 total
includes taxes & fees
Jul 2 - Jul 3
Williamstown Motel
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (351)
"conveniently located close to Williams and to 2 grocery stores, easy parking. Very new and clean"
The price is P11,380
P12,711 total
includes taxes & fees
Jul 8 - Jul 9
Fairfield Inn & Suites by Marriott Williamstown
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (942)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
The price is P10,084
P11,264 total
includes taxes & fees
Jul 2 - Jul 3
Jiminy Peak Mountain Resort
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (558)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is P12,394
P13,844 total
includes taxes & fees
Jul 6 - Jul 7
Courtyard by Marriott Lenox Berkshires
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?

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 Red Roof Inn PLUS+ South Deerfield – Amherst and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. 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 Swift River. You'll also find Mount Greylock and Barrington Stage Company 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.