Windsor Hotels from S$102

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Top 10 trending Windsor hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is S$182
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Wonderful place to stay"
The price is S$180
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (691)
"Great property. Would stay again"
The price is S$230
includes taxes & fees
26 Aug - 27 Aug
Berkshires Untold

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1966)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is S$170
includes taxes & fees
28 Aug - 29 Aug
Vacation Village in the Berkshires

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great location!"
The price is S$207
includes taxes & fees
22 Sept - 23 Sept
Hotel Downstreet, Ascend Hotel Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is S$234
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (525)
"Great place , love it, will return"
The price is S$215
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (700)
"Pleasant stay"
The price is S$149
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is S$318
includes taxes & fees
26 Aug - 27 Aug
The Red Lion Inn

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (584)
"Amazing place to stay. Can’t wait to go again. "
The price is S$124
includes taxes & fees
21 Sept - 22 Sept
Berkshire Mountain Lodge

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is S$102
includes taxes & fees
4 Sept - 5 Sept
FairBridge Inn Express

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (863)
"Consistently a clean room with welcoming staff."
The price is S$157
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is S$194
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (435)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is S$97
includes taxes & fees
27 Aug - 28 Aug
Berkshire Travel Lodge

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (867)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is S$158
includes taxes & fees
24 Aug - 25 Aug
Howard Johnson by Wyndham Williamstown

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (729)
"Great quiet stay. "
The price is S$128
includes taxes & fees
2 Sept - 3 Sept
The Villager Motel

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (625)
"It was lovely!"
The price is S$92
includes taxes & fees
4 Sept - 5 Sept
Econo Lodge Lee - Great Barrington

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is S$153
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is S$120
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"People live there. I'd stay again. I wouldn't take family. "
The price is S$154
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst
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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Learn more about Windsor

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Top Windsor Hotel 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 FairBridge Inn Express. 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 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, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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.