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Jun 12 - Jun 14
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Jun 19 - Jun 21

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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, (1,009 reviews)
"Clean room, great staff, parking"
United States
Gail
The price is ￥16,697
￥18,651 total
includes taxes & fees
Jul 1 - Jul 2
Red Roof Inn PLUS+ South Deerfield – Amherst
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, (1,001 reviews)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is ￥18,495
￥20,659 total
includes taxes & fees
Jun 15 - Jun 16
Best Western Plus Berkshire Hills Inn & Suites
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, (1,012 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ￥17,853
￥19,942 total
includes taxes & fees
Jun 14 - Jun 15
The Yankee Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ￥17,500
￥19,548 total
includes taxes & fees
Jun 14 - Jun 15
Quality Inn Lee - Lenox South
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ￥23,815
￥26,124 total
includes taxes & fees
Jun 17 - Jun 18
Shaker Mill Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (104 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is ￥23,922
￥26,720 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (913 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 ￥13,583
￥15,981 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Corner Motel
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, (1,009 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is ￥27,310
￥30,505 total
includes taxes & fees
Jun 18 - Jun 19
Hotel Downstreet, an Ascend Collection Hotel
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (611 reviews)
"Very well run property with good amenities and a lovely pool and sitting area. Lots of good attention to detail to make it a desirable place to stay!"
United States
Carolyn
The price is ￥18,463
￥20,624 total
includes taxes & fees
Jun 16 - Jun 17
Maple Terrace Motel
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, (864 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ￥12,683
￥14,167 total
includes taxes & fees
Jun 14 - Jun 15
Howard Johnson by Wyndham Lenox
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, (1,005 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is ￥22,573
￥25,214 total
includes taxes & fees
Jun 14 - Jun 15
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, (213 reviews)
"The whole place was beautifully well kept and the view couldn't be beat. Would definitely recommend to others and hope to return in the future."
United States
Jared
The price is ￥31,334
￥33,120 total
includes taxes & fees
Jun 24 - Jun 25
Blue Vista Motor Lodge
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (26 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ￥34,037
￥38,019 total
includes taxes & fees
Jun 17 - Jun 18
Element by Marriott Lenox Berkshires
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, (681 reviews)
"Five Star stay!"
United States
Adeline
The price is ￥25,527
￥28,513 total
includes taxes & fees
Jun 14 - Jun 15
Hilton Garden Inn Lenox Pittsfield
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (789 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is ￥14,289
￥15,960 total
includes taxes & fees
Jun 15 - Jun 16
The Villager Motel
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ￥12,146
￥13,566 total
includes taxes & fees
Jun 30 - Jul 1
Econo Lodge Lee - Great Barrington
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (975 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is ￥19,528
￥25,400 total
includes taxes & fees
Jun 14 - Jun 15
Berkshire Mountain Lodge
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (825 reviews)
"Quiet"
United States
William
The price is ￥11,187
￥12,497 total
includes taxes & fees
Jun 25 - Jun 26
FairBridge Inn Express
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (982 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is ￥22,764
￥25,428 total
includes taxes & fees
Jun 16 - Jun 17
Berkshires Untold
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (911 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is ￥17,659
￥19,725 total
includes taxes & fees
Jun 14 - Jun 15
Howard Johnson by Wyndham Williamstown
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"It's a beautiful resort. The room was literally like a home away from home. Very cozy, very clean. Has a full kitchen with a dishwasher"
Eileen 1-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

More cheap stays in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
The price is ￥16,697 per night from Jul 1 to Jul 2
￥16,697
￥18,651 total
Jul 1 - Jul 2
includes taxes & fees
7.2/10 Good! (1,009 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 Vacation Village in the Berkshires and Berkshires Untold. See all available top hotels, or vacation rentals in Windsor.
What's the top vacation rental in Windsor?
120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views: This vacation home rental outside of Windsor offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all 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 Mount Greylock 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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