Find hotels in Windsor, MA from AED 217

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Compare 935 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (80)
"Quaint and comfortable escape in a quiet village"
The price is AED 242
AED 414 total
includes taxes & fees
9 Apr - 10 Apr
Blooming Inn

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is AED 349
AED 513 total
includes taxes & fees
6 Apr - 7 Apr
Becket Motel

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (167)
"We had such a great stay at the Blue Vista Motor Lodge. The staff we encountered were welcoming and lovely. The room was super clean and had everything we needed for a comfortable stay. And the view! Incredible. "
The price is AED 656
AED 693 total
includes taxes & fees
14 Apr - 15 Apr
Blue Vista Motor Lodge

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (128)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is AED 638
AED 713 total
includes taxes & fees
6 Apr - 7 Apr
The Trail in Adams - Berkshires’ Art Hotel

The Revival House

3.0 star property
The price is AED 643
AED 718 total
includes taxes & fees
15 Apr - 16 Apr
The Revival House

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"We have been here about 5 times. Greay location. Good price."
The price is AED 465
AED 520 total
includes taxes & fees
27 Apr - 28 Apr
Hotel Downstreet, Ascend Hotel Collection

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (381)
"love porches!"
The price is AED 559
AED 780 total
includes taxes & fees
20 Apr - 21 Apr
The Porches Inn at Mass MoCA

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 988
AED 1,044 total
includes taxes & fees
7 Apr - 8 Apr
Harbour House Inn

Pilgrim Inn

2.5 star property
5.8 out of 10, (304)
"Very comfortable and in a convenient location"
The price is AED 253
AED 283 total
includes taxes & fees
4 May - 5 May
Pilgrim Inn

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Rooms wer clean and staff accomodating"
The price is AED 309
AED 345 total
includes taxes & fees
20 Apr - 21 Apr
Quality Inn

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is AED 307
AED 343 total
includes taxes & fees
14 Apr - 15 Apr
Sunset Inn

FairBridge Inn Express

2.5 star property
5.4 out of 10, (711)
"Friendly staff and quick checkin "
The price is AED 261
AED 292 total
includes taxes & fees
19 Apr - 20 Apr
FairBridge Inn Express

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 882
AED 985 total
includes taxes & fees
11 Apr - 12 Apr
Chambery Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 239
AED 267 total
includes taxes & fees
6 Apr - 7 Apr
Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is AED 915
AED 1,022 total
includes taxes & fees
6 Apr - 7 Apr
Devonfield Inn B&B

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Excellent"
The price is AED 340
AED 380 total
includes taxes & fees
17 Apr - 18 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection

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

3.5 star property
9.0 out of 10, Wonderful, (615)
"Clean and great location "
The price is AED 437
AED 540 total
includes taxes & fees
6 Apr - 7 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (629)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is AED 514
AED 575 total
includes taxes & fees
4 May - 5 May
Hilton Garden Inn Lenox Pittsfield

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is AED 217
AED 242 total
includes taxes & fees
9 Apr - 10 Apr
Wagon Wheel Inn

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (717)
"Staff friendly. Room comfortable. Location great."
The price is AED 275
AED 308 total
includes taxes & fees
1 May - 2 May
Howard Johnson by Wyndham Lenox
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

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Frequently asked questions

What's the best place to stay in Windsor?

Life House Berkshires, located 14.4 mi (23.1 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 The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental in Windsor?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Windsor is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books 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, Adams Theater, and Mount Greylock State Reservation Visitor Center. You'll also find Swift River 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.