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Our top choices for Windsor hotels

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is NZ$808
includes taxes & fees
20 Jan - 21 Jan
Inn at Kenmore Hall

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NZ$182
includes taxes & fees
6 Jan - 7 Jan
The Central Downtown Inn & Suites

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is NZ$327
includes taxes & fees
6 Jan - 7 Jan
Blue Vista Motor Lodge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841)
"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$158
includes taxes & fees
29 Jan - 30 Jan
Berkshire 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, (1002)
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$148
includes taxes & fees
7 Jan - 8 Jan
Best Western Plus Berkshire Hills Inn & Suites

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NZ$248
includes taxes & fees
9 Jan - 10 Jan
Hilton Garden Inn Lenox Pittsfield

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (451)
"It is the perfect place to stay!"
United States
Darrell
The price is NZ$317
includes taxes & fees
3 Feb - 4 Feb
The Porches Inn at Mass MoCA

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is NZ$153
includes taxes & fees
6 Jan - 7 Jan
Howard Johnson by Wyndham Lenox

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (811)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is NZ$289
includes taxes & fees
7 Jan - 8 Jan
Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1007)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NZ$190
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is NZ$250
includes taxes & fees
7 Jan - 8 Jan
Inn at Silver Maple Farm

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
"great stall and friendly pet friendly place"
United States
bonnie
The price is NZ$230
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (461)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is NZ$131
includes taxes & fees
6 Jan - 7 Jan
Berkshire Travel Lodge

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is NZ$366
includes taxes & fees
20 Jan - 21 Jan
Harbour House Inn

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, (72)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is NZ$237
includes taxes & fees
8 Jan - 9 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is NZ$767
includes taxes & fees
18 Jan - 19 Jan
33 Main

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (988)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is NZ$424
includes taxes & fees
6 Jan - 7 Jan
Jiminy Peak Mountain Resort

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
"Room spotless and staff helpful."
United States
William
The price is NZ$155
includes taxes & fees
18 Jan - 19 Jan
FairBridge Inn Express

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is NZ$486
includes taxes & fees
6 Jan - 7 Jan
The Inn at Stockbridge
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 accommodation 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 The Williams Inn. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. 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 Adams Theater, Mount Greylock State Reservation Visitor Center and Swift River. You'll also find Mount Greylock and Barrington Stage Company 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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