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May 29 - May 31
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Jun 5 - Jun 7

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Our top choices for Windsor hotels

Reception

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,010 reviews)
"Was great room was clean staff was nice"
United States
Theresa
The price is ₩163,483
₩182,610 total
includes taxes & fees
Jun 1 - Jun 2
Red Roof Inn PLUS+ South Deerfield – Amherst
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is ₩163,498
₩182,623 total
includes taxes & fees
May 31 - Jun 1
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ₩164,818
₩184,102 total
includes taxes & fees
Jun 15 - Jun 16
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (956 reviews)
"Clean and great job staffing "
United States
Pedro
The price is ₩174,147
₩228,033 total
includes taxes & fees
May 31 - Jun 1
Berkshire Mountain Lodge
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (607 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is ₩164,372
₩183,599 total
includes taxes & fees
Jun 1 - Jun 2
Maple Terrace Motel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is ₩157,435
₩249,747 total
includes taxes & fees
Jun 1 - Jun 2
Blooming Inn
Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Loved our stay. This property is very clean, well-maintained, and had everything we needed for a comfortable stay."
United States
Brianna
The price is ₩230,682
₩257,672 total
includes taxes & fees
May 31 - Jun 1
Hotel Downstreet, an Ascend Collection Hotel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Great location "
United States
Edith
The price is ₩169,573
₩189,403 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Lee - Lenox South
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"A nice stay at an affordable price. "
United States
Brian
The price is ₩125,398
₩140,083 total
includes taxes & fees
Jun 2 - Jun 3
Willows Motel Williamstown
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (910 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is ₩126,898
₩149,308 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Corner Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (962 reviews)
"Great stay!"
United States
Aditya
The price is ₩187,297
₩209,211 total
includes taxes & fees
Jun 2 - Jun 3
Berkshires Untold
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is ₩189,522
₩211,692 total
includes taxes & fees
Jun 1 - Jun 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (212 reviews)
"Great stay! "
United States
ALEKSey
The price is ₩304,946
₩322,331 total
includes taxes & fees
Jun 1 - Jun 2
Blue Vista Motor Lodge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (787 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is ₩133,498
₩149,113 total
includes taxes & fees
Jun 1 - Jun 2
The Villager Motel
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
United States
Sharon
The price is ₩182,998
₩204,403 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is ₩128,983
₩144,073 total
includes taxes & fees
Jun 1 - Jun 2
Berkshire Inn
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great breakfast."
United States
Linda
The price is ₩214,017
₩239,057 total
includes taxes & fees
Jun 2 - Jun 3
Hampton Inn & Suites Berkshires-Lenox
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (678 reviews)
"Clean room, staff was friendly and efficient. Great breakfast"
United States
Donna
The price is ₩215,473
₩240,683 total
includes taxes & fees
Jun 4 - Jun 5
Hilton Garden Inn Lenox Pittsfield
Property amenity

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (903 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is ₩174,147
₩223,847 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (856 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ₩118,498
₩132,361 total
includes taxes & fees
May 31 - Jun 1
Howard Johnson by Wyndham Lenox
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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Top Windsor Hotel Reviews

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

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

10/10 Excellent
"We arrived after hours and had a pleasant check in experience with security. We had a presidental room that had two kings and a kitchen plus a large living room for the kids to play. The room was clean and the overall property was clean and in good condition. The room also had a nice patio that overlooked the train tracks and was relaxing. Overall, the room was quiet and it was a great spot to reset. We took advantage of the on-site activities and gameroom. The kids enjoyed the playground behind the game room. We would recommend and stay again!"
Janette 8-night trip
Posted 14 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ₩118,498 per night from May 31 to Jun 1
₩118,498
₩132,361 total
May 31 - Jun 1
includes taxes & fees
7.6/10 Good! (856 reviews)

Frequently asked questions

What's the best place to stay in Windsor?
Berkshire Mountain Lodge, located 13 mi (20.9 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 Berkshires Untold and Vacation Village in the Berkshires. 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 Wahconah Falls State Park, Susan B. Anthony Birthplace Museum, and Adams Theater. You'll also find Mount Greylock State Reservation Visitor Center and Swift River 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.

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