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Check prices for these dates

Tonight
9 Apr - 10 Apr
Tomorrow
10 Apr - 11 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

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Our top choices for Windsor hotels

Reception

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)
"Comfy bed, nice front desk staff."
United States
Christina
The price is NZ$167
includes taxes & fees
14 Apr - 15 Apr
Red Roof Inn PLUS+ South Deerfield – Amherst
Front of property

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 NZ$277
includes taxes & fees
12 Apr - 13 Apr
Blooming Inn
Desk, laptop workspace, blackout curtains, iron/ironing board

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 NZ$134
includes taxes & fees
10 Apr - 11 Apr
Pleasant Valley Motel West Stockbridge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (892 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 NZ$178
includes taxes & fees
12 Apr - 13 Apr
Berkshires Untold
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,002 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 NZ$212
includes taxes & fees
13 Apr - 14 Apr
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 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 NZ$194
includes taxes & fees
23 Apr - 24 Apr
Quality Inn Lee - Lenox South
Lobby lounge

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 NZ$274
includes taxes & fees
15 Apr - 16 Apr
Element Lenox Berkshires
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (897 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 NZ$160
includes taxes & fees
13 Apr - 14 Apr
Cozy Corner Motel
55-inch LCD TV with digital channels, printers

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 NZ$288
includes taxes & fees
12 Apr - 13 Apr
The Revival House
Standard Room, 1 King Bed, Non Smoking

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 NZ$147
includes taxes & fees
15 Apr - 16 Apr
Rodeway Inn
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is NZ$247
includes taxes & fees
10 Apr - 11 Apr
Becket Motel
Garden

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 NZ$189
includes taxes & fees
13 Apr - 14 Apr
Shaker Mill Inn
Reception

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 NZ$151
includes taxes & fees
13 Apr - 14 Apr
The Villager Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (897 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is NZ$204
includes taxes & fees
10 May - 11 May
Berkshire Mountain Lodge
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is NZ$151
includes taxes & fees
10 Apr - 11 Apr
Howard Johnson by Wyndham Lenox
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is NZ$201
includes taxes & fees
21 Apr - 22 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Indoor pool

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, (88 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 NZ$226
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
View from property

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.4 out of 10, Exceptional, (315 reviews)
"Great location with easy parking"
United Kingdom
David
The price is NZ$141
includes taxes & fees
27 Apr - 28 Apr
Williamstown Motel
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (852 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is NZ$150
includes taxes & fees
3 May - 4 May
Berkshire Inn
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"Very comfortable bed and good hot shower. A good value for your money. Nice staff at front desk."
United States
Kathleen
The price is NZ$192
includes taxes & fees
13 Apr - 14 Apr
Sunset Inn
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

Hotel On North

Hotel On North

10/10 Excellent
"Charming hotel in the middle of Pittsfield. Love the art, decor and overall fell. Rooms are charming and cozy. Staff is friendly and welcoming. Great spot to stay with the kids (playroom downstairs is awesome). Love the touch of complementary coffee/tea/hot chocolate - always beautifully stocked and well maintained with great selection of products."
Karina 2-night trip
Posted 10 hours ago
Hotel On North

More cheap accommodation in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is NZ$151 per night from 10 Apr to 11 Apr
NZ$151
10 Apr - 11 Apr
includes taxes & fees
7.6/10 Good! (846 reviews)

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.
What are some of the best holiday rentals that Windsor has to offer?
Peace and quiet on the lake: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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! 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 Skyline Trail and Swift River 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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