Windsor Hotels from S$103

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Check Windsor hotel prices

Tonight
21 Nov - 22 Nov
Tomorrow night
22 Nov - 23 Nov
This weekend
22 Nov - 24 Nov
Next weekend
29 Nov - 1 Dec

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Top 10 trending Windsor hotels

The Williams Inn
Front of property – evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (371)
"This is the only hotel near Williams College but given that they have no competition it could have been much worse. They messed up our room type reservation (they gave us 2 queen beds instead of a king bed) and didn’t compensate us for that even though they said they would and we had to ask for our complimentary bottle of wine, but despite this, it’s still a nice hotel. Rooms are clean and restaurant is good. Very close to Williams College. I would stay again vs. staying further down the road at...
The price is S$296
includes taxes & fees
4 Dec - 5 Dec
The Williams Inn
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is S$262
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the Berkshires
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (442)
"Loved the stay, only two things kept me from saying it was 5 stars. The WiFi connection was spotty so if you were watching tv (because they use Apple TV) it was freezing every 2 mins. Also, you can’t lower the room temp passed 65 and their 65 wasn’t a normal 65. It was still really warm. Besides that I love it. Super clean and quiet. "
The price is S$180
includes taxes & fees
24 Nov - 25 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1002)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is S$140
includes taxes & fees
1 Dec - 2 Dec
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
8.0 out of 10, Very good, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is S$142
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is S$219
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Mountain Resort
Hotel On North
Front of property – evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (650)
"Beautiful room & exceptional staff. Highly recommend!"
The price is S$217
includes taxes & fees
25 Nov - 26 Nov
Hotel On North
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1042)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is S$174
includes taxes & fees
8 Dec - 9 Dec
Hotel Downstreet
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (411)
"Loved our room. Very clean"
The price is S$274
includes taxes & fees
23 Nov - 24 Nov
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1010)
"Staff very helpful and friendly "
The price is S$177
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn & Suites Berkshires-Lenox
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (747)
"Good. No highlights."
The price is S$129
includes taxes & fees
24 Nov - 25 Nov
Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is S$135
includes taxes & fees
3 Dec - 4 Dec
Best Western Plus Berkshire Hills Inn & Suites
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is S$177
includes taxes & fees
11 Dec - 12 Dec
Courtyard by Marriott Lenox Berkshires
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.4 out of 10, (678)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is S$118
includes taxes & fees
24 Nov - 25 Nov
FairBridge Inn Express
The Porches Inn at Mass MoCA
Exterior
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (369)
"We had an excellent time and loved all the beautiful details. Will definitely stay here again."
The price is S$264
includes taxes & fees
22 Dec - 23 Dec
The Porches Inn at Mass MoCA
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is S$118
includes taxes & fees
23 Nov - 24 Nov
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Pool
Howard Johnson by Wyndham Williamstown
2.0 star property
6.4 out of 10, (824)
"Staff was very kind and welcoming!"
The price is S$150
includes taxes & fees
24 Nov - 25 Nov
Howard Johnson by Wyndham Williamstown
Hilton Garden Inn Lenox Pittsfield
Terrace/patio
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is S$206
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Fairfield Inn & Suites by Marriott Williamstown
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (308)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is S$201
includes taxes & fees
8 Dec - 9 Dec
Fairfield Inn & Suites by Marriott Williamstown
Wagon Wheel Inn
Property grounds
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is S$103
includes taxes & fees
26 Nov - 27 Nov
Wagon Wheel 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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Frequently asked questions

What's the best place to stay in Windsor?

The Red Lion Inn, located 20.7 mi (33.4 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 Life House Berkshires and The Yankee, Trademark Collection by Wyndham. 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 are some hotels with pools in Windsor?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are two additional hotels that feature an on-site pool. View all hotels with pools 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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest. You'll also find Mount Greylock and Berkshire Museum 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.