Find hotels in Windsor, MA from ￥11,884

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Compare 978 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Desk, laptop workspace, blackout drapes, iron/ironing board
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, (1000)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is ￥12,161
￥13,583 total
includes taxes & fees
Dec 9 - Dec 10
Red Roof Inn PLUS+ South Deerfield – Amherst
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (123)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
The price is ￥10,472
￥19,297 total
includes taxes & fees
Dec 8 - Dec 9
Blooming Inn
Lobby sitting area
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ￥14,502
￥16,200 total
includes taxes & fees
Dec 8 - Dec 9
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is ￥13,863
￥15,485 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
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, (1003)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ￥16,636
￥18,583 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
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, (980)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,259
￥15,927 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,719
￥17,558 total
includes taxes & fees
Dec 15 - Dec 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is ￥16,084
￥17,643 total
includes taxes & fees
Dec 9 - Dec 10
Shaker Mill Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ￥20,322
￥22,699 total
includes taxes & fees
Dec 21 - Dec 22
Element Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is ￥10,704
￥11,956 total
includes taxes & fees
Dec 7 - Dec 8
The Villager Motel
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
The price is ￥11,588
￥13,679 total
includes taxes & fees
Dec 10 - Dec 11
Cozy Corner Motel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is ￥14,062
￥15,707 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥23,412
￥33,083 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Red Lion Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ￥16,010
￥17,884 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn & Suites Berkshires-Lenox
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,255
￥13,688 total
includes taxes & fees
Dec 7 - Dec 8
Howard Johnson by Wyndham Lenox
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is ￥13,548
￥15,133 total
includes taxes & fees
Dec 14 - Dec 15
Williamstown Motel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (778)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ￥8,074
￥8,857 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ￥13,001
￥14,522 total
includes taxes & fees
Dec 12 - Dec 13
Berkshire Inn
Courtyard
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is ￥16,695
￥18,314 total
includes taxes & fees
Dec 7 - Dec 8
The Springs Motel
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 ￥12,161 per night from Dec 9 to Dec 10
￥12,161
￥13,583 total
Dec 9 - Dec 10
includes taxes & fees
7/10 Good! (1,014 reviews)

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 Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Windsor.
What's the top vacation rental in Windsor?
Peace and quiet on the lake: This vacation home rental outside of Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. 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, Crane Museum of Papermaking, and Mount Greylock State Reservation Visitor Center. You'll also find Skyline Trail 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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