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Check prices for these dates

This weekend
12 June - 14 June
Next weekend
19 June - 21 June

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Our top choices for Windsor hotels

Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (137 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 AU$218
includes taxes & fees
10 June - 11 June
Blooming Inn
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AU$176
includes taxes & fees
22 June - 23 June
The Yankee Inn
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is AU$203
includes taxes & fees
9 June - 10 June
Berkshire Lake Lodge
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, (1,005 reviews)
"Clean room, great staff, parking"
United States
Gail
The price is AU$165
includes taxes & fees
1 July - 2 July
Red Roof Inn PLUS+ South Deerfield – Amherst
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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 AU$176
includes taxes & fees
11 June - 12 June
Best Western Plus Berkshire Hills Inn & Suites
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (912 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 AU$141
includes taxes & fees
9 June - 10 June
Cozy Corner Motel
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is AU$192
includes taxes & fees
13 June - 14 June
Becket Motel
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (32 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is AU$241
includes taxes & fees
8 July - 9 July
The Revival House
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (460 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$211
includes taxes & fees
10 June - 11 June
Shaker Mill Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (977 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is AU$198
includes taxes & fees
11 June - 12 June
Berkshires Untold
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, (863 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AU$125
includes taxes & fees
9 June - 10 June
Howard Johnson by Wyndham Lenox
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (468 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is AU$104
includes taxes & fees
9 June - 10 June
Berkshire Travel Lodge
BBQ/picnic Area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.8 out of 10, Excellent, (5 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is AU$176
includes taxes & fees
9 June - 10 June
Hideaway Inn Lenox
Shower, free toiletries, hair dryer, towels

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (246 reviews)
"Had a great stay."
United States
Trevor
The price is AU$114
includes taxes & fees
15 June - 16 June
Rodeway Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AU$194
includes taxes & fees
11 June - 12 June
Quality Inn Lee - Lenox South
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 AU$141
includes taxes & fees
10 June - 11 June
The Villager Motel
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, (101 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 AU$214
includes taxes & fees
14 June - 15 June
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is AU$97
includes taxes & fees
16 June - 17 June
Pleasant Valley Motel West Stockbridge
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)
"Great stay "
United States
Brian
The price is AU$127
includes taxes & fees
10 June - 11 June
Berkshire Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is AU$303
includes taxes & fees
22 June - 23 June
The Red Lion Inn
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."
Rachel 1-night trip
Posted 3 hours ago
The Yankee Inn

More cheap accommodation 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 AU$165 per night from 1 July to 2 July
AU$165
1 July - 2 July
includes taxes & fees
7.2/10 Good! (1,005 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 traveller 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 are some of the best holiday rentals that Windsor has to offer?
120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views: This holiday home rental outside of Windsor offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
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 accommodation options 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. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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