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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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Our top choices for Windsor hotels

Exterior
Blue Vista Motor Lodge

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
12 Jan - 13 Jan
Blue Vista Motor Lodge
Outdoor pool
Berkshire Travel 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$122
includes taxes & fees
11 Jan - 12 Jan
Berkshire Travel Lodge
Exterior
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (452)
"It is the perfect place to stay!"
United States
Darrell
The price is NZ$317
includes taxes & fees
9 Feb - 10 Feb
The Porches Inn at Mass MoCA
Exterior
Harbour House Inn

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$394
includes taxes & fees
12 Jan - 13 Jan
Harbour House Inn
Lobby
Inn at Kenmore Hall

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
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (353)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NZ$182
includes taxes & fees
9 Feb - 10 Feb
The Central Downtown Inn & Suites
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is NZ$336
includes taxes & fees
10 Jan - 11 Jan
The Trail in Adams - Berkshires’ Art Hotel
Luxury Room, 1 King Bed, Bathtub
33 Main

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$770
includes taxes & fees
18 Jan - 19 Jan
33 Main
Exterior detail
Hampton Terrace Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is NZ$423
includes taxes & fees
13 Jan - 14 Jan
Hampton Terrace Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

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$157
includes taxes & fees
9 Feb - 10 Feb
Berkshire Inn
55-inch LCD TV with digital channels, printers
The Revival House

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
"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$290
includes taxes & fees
11 Jan - 12 Jan
The Revival House
Exterior
Jiminy Peak Mountain Resort

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
11 Jan - 12 Jan
Jiminy Peak Mountain Resort
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

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
22 Jan - 23 Jan
FairBridge Inn Express
Front of property
Gateways Inn & Restaurant

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (195)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is NZ$321
includes taxes & fees
2 Feb - 3 Feb
Gateways Inn & Restaurant
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NZ$248
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

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
11 Jan - 12 Jan
Howard Johnson by Wyndham Lenox
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1002)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is NZ$190
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Whitlock

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (283)
"great location"
United States
Brian
The price is NZ$244
includes taxes & fees
11 Jan - 12 Jan
The Whitlock
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Best Western Plus Berkshire Hills Inn & Suites

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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$148
includes taxes & fees
8 Feb - 9 Feb
Best Western Plus Berkshire Hills Inn & Suites
Aerial view
Inn at Silver Maple Farm

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
21 Jan - 22 Jan
Inn at Silver Maple Farm
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The staff were very nice, the room was clean and generally pleasant. the beds were not bad. They provide a continental-style breakfast, which is something. They are also dog-friendly! And there is a wonderful Indian restaurant that is adjacent to the hotel, and it is good! The only negative was a bit of mold, presumably causing some sinus issues, but that is to be expected in a hotel right on a lake like this. Otherwise, we would certainly stay there again."
Jonathan 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

More cheap accommodation in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is NZ$153 per night from 11 Jan to 12 Jan
NZ$153
11 Jan - 12 Jan
includes taxes & fees
7.4/10 Good! (827 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 Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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 Mount Greylock State Reservation Visitor Center, Skyline Trail 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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