Find hotels in Windsor, MA from ￥11,947

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windsor hotels

Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst

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 ￥13,332
￥14,892 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Red Roof Inn PLUS+ South Deerfield – Amherst
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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)
"Very friendly and good Breakfast."
United States
Jesse
The price is ￥11,910
￥13,304 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is ￥12,351
￥21,437 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Blooming Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ￥14,448
￥16,139 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ￥15,641
￥17,471 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥13,754
￥15,363 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
The price is ￥11,102
￥13,124 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Cozy Corner Motel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ￥19,485
￥21,765 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Hotel Downstreet, an Ascend Collection Hotel
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is ￥13,122
￥14,657 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Quality Inn Lee - Lenox South
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is ￥27,849
￥29,437 total
includes taxes & fees
Dec 28 - Dec 29
Blue Vista Motor Lodge
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ￥21,052
￥23,516 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (767)
"It's very good for stay over"
United States
Frances
The price is ￥10,760
￥12,018 total
includes taxes & fees
Dec 28 - Dec 29
The Villager Motel
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ￥19,942
￥22,275 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ￥22,456
￥32,051 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Red Lion Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ￥16,218
￥18,116 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Berkshires-Lenox
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,319
￥13,760 total
includes taxes & fees
Dec 28 - Dec 29
Howard Johnson by Wyndham Lenox
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (996)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is ￥11,929
￥13,325 total
includes taxes & fees
Dec 28 - Dec 29
Willows Motel Williamstown
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (592)
"Cute place"
United States
Lisa
The price is ￥15,438
￥17,244 total
includes taxes & fees
Dec 28 - Dec 29
Maple Terrace Motel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
The price is ￥17,964
￥19,707 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Shaker Mill Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ￥15,409
￥20,699 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Berkshire Mountain Lodge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ￥12,319 per night from Dec 28 to Dec 29
￥12,319
￥13,760 total
Dec 28 - Dec 29
includes taxes & fees
7.4/10 Good! (827 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 The Williams Inn. 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, 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.

Explore a world of travel with Expedia