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Our top choices for Windsor hotels

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, (1,000 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is Rp1.801.797
Rp2.012.608 total
includes taxes & fees
30 Mar - 31 Mar
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (24 reviews)
"The hotel is very nice the lobby is nice for hang out with water tea and coffee, the rooms are new and modern and I loved the kitchenette it had all the amenities you need, the only downside is th rooms are very small like city hotel room small and there’s not enough light in the room not making it ideal to hang out in the room, other then that it was a nice pleasent stay."
United States
Chaya
The price is Rp2.349.656
Rp2.624.567 total
includes taxes & fees
9 Apr - 10 Apr
Element Lenox Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is Rp1.424.669
Rp1.591.355 total
includes taxes & fees
14 Apr - 15 Apr
Quality Inn Lee - Lenox South

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (881 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is Rp1.180.575
Rp1.318.703 total
includes taxes & fees
1 Apr - 2 Apr
Berkshires Untold

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (27 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is Rp2.536.952
Rp2.833.618 total
includes taxes & fees
29 Mar - 30 Mar
The Revival House

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is Rp1.842.536
Rp2.021.261 total
includes taxes & fees
31 Mar - 1 Apr
Shaker Mill Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is Rp1.582.214
Rp2.595.630 total
includes taxes & fees
29 Mar - 30 Mar
Blooming Inn

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, (1,000 reviews)
"Comfy bed, nice front desk staff."
United States
Christina
The price is Rp1.436.508
Rp1.604.579 total
includes taxes & fees
19 Apr - 20 Apr
Red Roof Inn PLUS+ South Deerfield – Amherst

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (599 reviews)
"Very clean room. Service excellent. "
United States
John
The price is Rp1.673.496
Rp1.869.244 total
includes taxes & fees
29 Mar - 30 Mar
Maple Terrace Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (896 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is Rp1.338.797
Rp1.577.819 total
includes taxes & fees
29 Mar - 30 Mar
Cozy Corner Motel

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is Rp1.665.738
Rp1.860.668 total
includes taxes & fees
29 Mar - 30 Mar
The Yankee, Trademark Collection by Wyndham

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (783 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is Rp1.267.800
Rp1.416.217 total
includes taxes & fees
29 Mar - 30 Mar
The Villager Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is Rp2.241.360
Rp2.503.531 total
includes taxes & fees
6 Apr - 7 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is Rp3.803.400
Rp4.020.194 total
includes taxes & fees
29 Mar - 30 Mar
UU Rowe Camp and Conference Center

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is Rp988.884
Rp1.084.805 total
includes taxes & fees
29 Mar - 30 Mar
Pleasant Valley Motel West Stockbridge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (207 reviews)
"Great stay! "
United States
ALEKSey
The price is Rp3.072.946
Rp3.248.103 total
includes taxes & fees
1 Apr - 2 Apr
Blue Vista Motor Lodge

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is Rp1.217.088
Rp1.359.487 total
includes taxes & fees
5 Apr - 6 Apr
Rodeway Inn

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great stay, great breakfast"
United States
Peter
The price is Rp1.752.336
Rp1.957.359 total
includes taxes & fees
5 Apr - 6 Apr
Hampton Inn & Suites Berkshires-Lenox

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is Rp1.616.496
Rp1.805.625 total
includes taxes & fees
19 Apr - 20 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (840 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is Rp1.335.416
Rp1.491.609 total
includes taxes & fees
29 Mar - 30 Mar
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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Top Windsor Hotel Reviews

More cheap stays in Windsor

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 traveller 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.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
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 accommodation options 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, Susan B. Anthony Birthplace Museum and Mount Greylock State Reservation Visitor Center. You'll also find Swift River and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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