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Our top choices for Windsor hotels

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, (1,001 reviews)
"Clean room, nice staff, lots of parking. "
United States
Ben
The price is ฿3,448
฿3,851 total
includes taxes & fees
7 May - 8 May
Red Roof Inn PLUS+ South Deerfield – Amherst

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 ฿3,651
฿5,656 total
includes taxes & fees
27 Apr - 28 Apr
Blooming Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (912 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
The price is ฿2,758
฿3,081 total
includes taxes & fees
28 Apr - 29 Apr
Berkshires Untold

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is ฿3,216
฿3,593 total
includes taxes & fees
26 Apr - 27 Apr
The Yankee Inn

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)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is ฿3,274
฿3,657 total
includes taxes & fees
28 Apr - 29 Apr
Best Western Plus Berkshire Hills Inn & Suites

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (900 reviews)
"Immaculate room, great staff, very complete breakfast, best coffee I've had in any motel. Highly recommend for anyone visiting the Williamstown area "
United States
James
The price is ฿2,550
฿3,005 total
includes taxes & fees
30 Apr - 1 May
Cozy Corner Motel

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is ฿4,445
฿4,965 total
includes taxes & fees
30 Apr - 1 May
The Revival House

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is ฿3,509
฿3,850 total
includes taxes & fees
27 Apr - 28 Apr
Shaker Mill Inn

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 ฿2,289
฿2,511 total
includes taxes & fees
26 Apr - 27 Apr
Pleasant Valley Motel West Stockbridge

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 location "
United States
Edith
The price is ฿3,313
฿3,700 total
includes taxes & fees
19 May - 20 May
Quality Inn Lee - Lenox South

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is ฿2,543
฿2,841 total
includes taxes & fees
27 Apr - 28 Apr
The Villager Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is ฿3,348
฿3,740 total
includes taxes & fees
28 Apr - 29 Apr
Maple Terrace Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is ฿2,543
฿2,841 total
includes taxes & fees
26 Apr - 27 Apr
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (915 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is ฿2,672
฿3,710 total
includes taxes & fees
30 Apr - 1 May
Berkshire Mountain Lodge

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, (91 reviews)
"Clean rooms, friendly staff, pool was very clean and so is the hot tub. Breakfast was okay. Overall our stay was excellent. Highly recommended."
United States
Camille
The price is ฿4,185
฿4,675 total
includes taxes & fees
25 May - 26 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (241 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 ฿2,737
฿3,057 total
includes taxes & fees
27 Apr - 28 Apr
Rodeway Inn

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 ฿6,519
฿6,891 total
includes taxes & fees
26 Apr - 27 Apr
UU Rowe Camp and Conference Center

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
The price is ฿3,455
฿3,790 total
includes taxes & fees
26 Apr - 27 Apr
The Springs Motel

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
"A nice stay at an affordable price. "
United States
Brian
The price is ฿2,600
฿2,904 total
includes taxes & fees
26 Apr - 27 Apr
Willows Motel Williamstown

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ฿5,719
฿6,389 total
includes taxes & fees
3 May - 4 May
Element Lenox Berkshires
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?
Berkshires Untold, located 14.4 mi (23.1 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 Vacation Village in the Berkshires 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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