Windsor Hotels

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Check prices for these dates

Tonight
26 Feb - 27 Feb
Tomorrow
27 Feb - 28 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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Guest rating
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Our top choices for Windsor hotels

Family House | Terrace/patio

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is €128
includes taxes & fees
27 Feb - 28 Feb
Becket Motel
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (202 reviews)
"Great stay! "
United States
ALEKSey
The price is €160
includes taxes & fees
2 Mar - 3 Mar
Blue Vista Motor Lodge
Lobby sitting area

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "
United States
Cameron
The price is €60
includes taxes & fees
4 Mar - 5 Mar
Berkshire Travel Lodge
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is €534
includes taxes & fees
27 Feb - 28 Feb
Inn at Kenmore Hall
Exterior

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (459 reviews)
"The great people!!!"
United States
Julie
The price is €155
includes taxes & fees
29 Mar - 30 Mar
The Porches Inn at Mass MoCA
Terrace/patio

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is €96
includes taxes & fees
1 Mar - 2 Mar
The Central Downtown Inn & Suites
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is €227
includes taxes & fees
2 Mar - 3 Mar
Harbour House Inn
Exterior

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is €467
includes taxes & fees
5 Mar - 6 Mar
33 Main
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is €207
includes taxes & fees
27 Feb - 28 Feb
Hampton Terrace Inn
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 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 €85
includes taxes & fees
1 Mar - 2 Mar
Berkshire Inn
Daily to-go breakfast for a fee

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is €179
includes taxes & fees
8 Mar - 9 Mar
Jiminy Peak Mountain Resort
Terrace/patio

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 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is €164
includes taxes & fees
1 Mar - 2 Mar
The Trail in Adams - Berkshires’ Art Hotel
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (668 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is €128
includes taxes & fees
22 Mar - 23 Mar
Hilton Garden Inn Lenox Pittsfield
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, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is €65
includes taxes & fees
1 Mar - 2 Mar
Howard Johnson by Wyndham Lenox
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is €113
includes taxes & fees
24 Mar - 25 Mar
Inn at Silver Maple Farm
Restaurant

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, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is €94
includes taxes & fees
28 Feb - 1 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
United States
Miguel
The price is €186
includes taxes & fees
5 Mar - 6 Mar
Gateways Inn & Restaurant
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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is €91
includes taxes & fees
1 Mar - 2 Mar
Best Western Plus Berkshire Hills Inn & Suites
Exterior

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (290 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is €113
includes taxes & fees
2 Mar - 3 Mar
The Whitlock
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, (26 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 €142
includes taxes & fees
1 Mar - 2 Mar
The Revival House
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great! Go annually. Highly recommend "
Joseph 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is €65 per night from 1 Mar to 2 Mar
€65
1 Mar - 2 Mar
includes taxes & fees
7.6/10 Good! (834 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 Berkshire Mountain Lodge 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 Bas Ridge Golf Course, Mount Greylock State Reservation Visitor Center and Skyline Trail. You'll also find Mount Greylock and Berkshire Athenaeum 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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