Find hotels in Windsor, MA from AED 253

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Check Windsor hotel prices

Tonight
26 Dec - 27 Dec
Tomorrow night
27 Dec - 28 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

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Compare 898 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (390)
"Just an overnight stay during pre Christmas lull. However, my wife and I were delighted with the excellent accommodations and sevice. They did a beautiful job creating a 21st Century version of this inn at their new location behind Main Street. I would happily stay there again. "
The price is AED 615
AED 687 total
includes taxes & fees
1 Jan - 2 January 2025
The Williams Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (458)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."
The price is AED 326
AED 364 total
includes taxes & fees
1 Jan - 2 January 2025
Life House Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (703)
"Staff was very accommodating. The pool area was quite nice and it was deep"
The price is AED 364
AED 406 total
includes taxes & fees
5 Jan - 6 January 2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great check in experience. "
The price is AED 356
AED 398 total
includes taxes & fees
2 Jan - 3 January 2025
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (668)
"Very large room with a huge desk and two arm chairs. The bathroom was nice with a large walk-in shower and a rain shower head. My room faced North street, so I noticed the noise from the road, but most wouldn’t notice. Very pleased"
The price is AED 477
AED 533 total
includes taxes & fees
2 Jan - 3 January 2025
Hotel On North
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Hotel Downstreet
Exterior

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1001)
"Stayed for a weekend wedding and it was a great location. Room was large "
The price is AED 426
AED 476 total
includes taxes & fees
9 Jan - 10 January 2025
Hotel Downstreet
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"nice & quiet at night with a good solid breakfast in the morning"
The price is AED 465
AED 520 total
includes taxes & fees
7 Jan - 8 January 2025
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Exterior

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (542)
"Staff were pleasant and helpful. Limited menu at the hotel's bistro, but two restaurants across the busy road. Pool is much smaller than it looks in the photo and hot tub was too hot. Rooms somewhat small but well laid-out."
The price is AED 529
AED 591 total
includes taxes & fees
13 Jan - 14 January 2025
Courtyard by Marriott Lenox Berkshires
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (417)
"Good"
The price is AED 606
AED 750 total
includes taxes & fees
1 Jan - 2 January 2025
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Super friendly front desk staffs. We had wonderful time. "
The price is AED 346
AED 387 total
includes taxes & fees
6 Jan - 7 January 2025
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (371)
"The Porches is always a treasure in the midst of chain hotels. Just the right balance of "old school" with contemporary charm. It's the place to stay in North Adams if you can get in!!"
The price is AED 528
AED 651 total
includes taxes & fees
26 Jan - 27 January 2025
The Porches Inn at Mass MoCA
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (753)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is AED 316
AED 353 total
includes taxes & fees
29 Dec - 30 Dec
Berkshire Inn
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (687)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is AED 253
AED 283 total
includes taxes & fees
27 Dec - 28 Dec
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (622)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is AED 515
AED 575 total
includes taxes & fees
12 Jan - 13 January 2025
Hilton Garden Inn Lenox Pittsfield
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (405)
"It’s unique historical property. The front desk allowed us to check in three hours early due to it’s a snowy day. We had a lovely thanksgiving dinner in the restaurant belongs to the hotel. "
The price is AED 278
AED 310 total
includes taxes & fees
31 Dec - 1 January 2025
1896 House Country Inn & Motels
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (309)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is AED 558
AED 624 total
includes taxes & fees
13 Jan - 14 January 2025
Fairfield Inn & Suites by Marriott Williamstown
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (703)
"Manager was helpful. The heating system was loud and although the manager tried to fix it , the noise disrupted sleep. "
The price is AED 290
AED 324 total
includes taxes & fees
1 Jan - 2 January 2025
Howard Johnson by Wyndham Lenox
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (493)
"Amazing location and service!"
Club Wyndham Bentley Brook
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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Frequently asked questions

What's the best place to stay in Windsor?

Hotel Downstreet, located 13.6 mi (21.9 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 Life House Berkshires and The Red Lion Inn. 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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center, and Mohawk Trail State Forest. You'll also find Mount Greylock and Berkshire Athenaeum 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.