Find hotels in Windsor, MA from SAR 259

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21 Jul - 22 Jul
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22 Jul - 23 Jul
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25 Jul - 27 Jul
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Compare 993 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1003)
"Good Location"
The price is SAR 435
SAR 486 total
includes taxes & fees
31 Jul - 1 Aug
Red Roof Inn PLUS+ South Deerfield – Amherst
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (105)
"Great Place to stay in Small town"
The price is SAR 330
SAR 515 total
includes taxes & fees
18 Aug - 19 Aug
Blooming Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is SAR 321
SAR 484 total
includes taxes & fees
29 Jul - 30 Jul
Becket Motel
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (175)
"Lovely stay!"
The price is SAR 789
SAR 834 total
includes taxes & fees
22 Jul - 23 Jul
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (131)
"Stayed only one night Very cosy, quiet place "
The price is SAR 670
SAR 749 total
includes taxes & fees
22 Jul - 23 Jul
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
Romantic Room, 1 King Bed (Room 4) | 1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (5)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is SAR 675
SAR 754 total
includes taxes & fees
22 Jul - 23 Jul
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great place"
The price is SAR 603
SAR 673 total
includes taxes & fees
19 Aug - 20 Aug
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is SAR 794
SAR 971 total
includes taxes & fees
19 Aug - 20 Aug
The Porches Inn at Mass MoCA
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is SAR 885
SAR 936 total
includes taxes & fees
23 Jul - 24 Jul
Harbour House Inn
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is SAR 294
SAR 329 total
includes taxes & fees
3 Aug - 4 Aug
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Friendly staff, easy parking"
The price is SAR 507
SAR 566 total
includes taxes & fees
4 Aug - 5 Aug
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (392)
"No frills but it was a great stay!"
The price is SAR 392
SAR 438 total
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (749)
"Close to our target event a plus"
The price is SAR 267
SAR 298 total
includes taxes & fees
3 Aug - 4 Aug
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (611)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is SAR 239
SAR 267 total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful location!"
The price is SAR 730
SAR 816 total
includes taxes & fees
30 Jul - 31 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (678)
"Had a great time"
The price is SAR 620
SAR 745 total
includes taxes & fees
24 Jul - 25 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is SAR 666
SAR 744 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is SAR 719
SAR 803 total
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield
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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Learn more about Windsor

Explore Windsor: its food and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"We enjoyed the unique character and flavor of the hotel!"
Brad 3-night trip
Posted 2 days ago
Berkshires Untold

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 Red Roof Inn PLUS+ South Deerfield – Amherst and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental in Windsor?

Spacious 5-bedroom house in charming Lee with WiFi: This vacation home rental outside of Windsor offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly. 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 Bas Ridge Golf Course, Mount Greylock State Reservation Visitor Center, and Mount Greylock. You'll also find Barrington Stage Company and Berkshire Museum 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.