Windsor Hotels from S$97

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Tonight
22 Jun - 23 Jun
Tomorrow
23 Jun - 24 Jun
Next weekend
27 Jun - 29 Jun
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4 Jul - 6 Jul

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Top 10 trending Windsor hotels

Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (559)
"A great place to stay in Williamstown. Beautiful garden, friendly staff, very comfortable."
The price is S$165
includes taxes & fees
25 Jun - 26 Jun
Maple Terrace Motel
Blue Vista Motor Lodge
1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (172)
"Lovely stay!"
The price is S$272
includes taxes & fees
23 Jun - 24 Jun
Blue Vista Motor Lodge
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (825)
"Great classic motel. Clean. Friendly, helpful staff."
The price is S$135
includes taxes & fees
29 Jun - 30 Jun
Cozy Corner Motel
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (737)
"Best hotel in the Berkshire! "
The price is S$216
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (390)
"Phenomenal room, staff and location! We loved The Porches!!"
The price is S$312
includes taxes & fees
29 Jun - 30 Jun
The Porches Inn at Mass MoCA
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is S$326
includes taxes & fees
25 Jun - 26 Jun
The Red Lion Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (126)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (922)
"Clean, conscientious service, great breakast spread. "
The price is S$115
includes taxes & fees
23 Jun - 24 Jun
Willows Motel Williamstown
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."
The price is S$207
includes taxes & fees
21 Jul - 22 Jul
Hotel Downstreet, Ascend Hotel Collection
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (493)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$282
includes taxes & fees
25 Jun - 26 Jun
Hilton Garden Inn Lenox Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great place to stay "
The price is S$145
includes taxes & fees
1 Jul - 2 Jul
Best Western Plus Berkshire Hills Inn & Suites
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (348)
"It's a quick drive to Williams campus."
The price is S$229
includes taxes & fees
26 Jun - 27 Jun
Fairfield Inn & Suites by Marriott Williamstown
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (313)
"Gorgeous place with clean room and excellent areas to have breakfast, read, and relax. Friendly staff and easy checking process. Would stay here again!"
The price is S$224
includes taxes & fees
30 Jun - 1 Jul
The Dewey
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (546)
"Very clean and very nice staff. Breakfast was great"
The price is S$213
includes taxes & fees
24 Jun - 25 Jun
Berkshire Valley Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Quiet, clean, great proximity to places and destinations. "
The price is S$171
includes taxes & fees
30 Jun - 1 Jul
The Yankee, Trademark Collection by Wyndham
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (45)
"Springs Motel has a one of a kind vibe, loved the Double bed room! & managed by experienced, friendly people. Can’t wait to book a cabin next time with my family !! "
The price is S$188
includes taxes & fees
23 Jun - 24 Jun
The Springs Motel
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The price is S$330
includes taxes & fees
13 Jul - 14 Jul
The Ponds at Foxhollow
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Stayed only one night Very cosy, quiet place "
The price is S$250
includes taxes & fees
23 Jun - 24 Jun
The Trail in Adams - Berkshires’ Art Hotel
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

Explore Windsor: its dining and more!

See all hotels in Windsor

Frequently asked questions

What's the best place to stay in Windsor?

Red Roof Inn PLUS+ South Deerfield – Amherst, located 22.1 mi (35.5 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 The Yankee, Trademark Collection by Wyndham and Vacation Village in the Berkshires. 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 Wahconah Falls State Park, 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.