Default HTG hotel image

Windsor Hotels from S$86

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
17 Jul - 19 Jul
Next weekend
24 Jul - 26 Jul

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Windsor hotels

Hotel
Exterior

Historic Beaver Mill Inn

Historic Beaver Mill Inn
2.0 star property
North Adams
The price is S$199
includes taxes & fees
15 Jul - 16 Jul
Historic Beaver Mill Inn
Exterior

Shelburne Springs

Shelburne Springs
2.0 star property
Shelburne
The price is S$583
includes taxes & fees
10 Aug - 11 Aug
Shelburne Springs
Reception

Red Roof Inn PLUS+ South Deerfield ā€“ Amherst

Red Roof Inn PLUS+ South Deerfield ā€“ Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,011 reviews)
"Clean and convenient!"
United States
Katie
The price is S$143
includes taxes & fees
4 Aug - 5 Aug
Red Roof Inn PLUS+ South Deerfield ā€“ Amherst
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (141 reviews)
The price is S$234
includes taxes & fees
26 Jul - 27 Jul
Blooming Inn
In-room safe, desk, laptop workspace, blackout curtains

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, (1,006 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is S$172
includes taxes & fees
26 Jul - 27 Jul
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (133 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is S$251
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (852 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is S$86
includes taxes & fees
2 Aug - 3 Aug
FairBridge Inn Express
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, (36 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is S$239
includes taxes & fees
15 Jul - 16 Jul
The Revival House
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (928 reviews)
"Very nice and cute place to stay. Staff was very friendly and helpful. Room was nice and clean. Very quiet with beautiful outside property. The only problem was no coffee or breakfast until 8am."
United States
Tracy
The price is S$138
includes taxes & fees
21 Jul - 22 Jul
Cozy Corner Motel
Childrenā€™s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,003 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is S$96
includes taxes & fees
23 Jul - 24 Jul
Pleasant Valley Motel West Stockbridge
Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (257 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
The price is S$116
includes taxes & fees
20 Jul - 21 Jul
Rodeway Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,013 reviews)
"Great place"
United States
Michelle
The price is S$191
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Lee - Lenox South
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is S$201
includes taxes & fees
15 Jul - 16 Jul
Becket Motel
View from property

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (331 reviews)
"Clean rooms and the staff was extremely friendly and helpful"
United States
Graham
The price is S$132
includes taxes & fees
21 Jul - 22 Jul
Williamstown Motel
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is S$262
includes taxes & fees
30 Jul - 31 Jul
Berkshire Lake Lodge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (800 reviews)
"The price in this area is expensive and this motel provides a reasonable alternative!"
United States
qing
The price is S$143
includes taxes & fees
22 Jul - 23 Jul
The Villager Motel
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (424 reviews)
"Nice place for a stay"
United States
Jay
The price is S$158
includes taxes & fees
22 Jul - 23 Jul
Sunset Inn
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, (883 reviews)
"Great place"
United States
Luciane
The price is S$143
includes taxes & fees
15 Jul - 16 Jul
Howard Johnson by Wyndham Lenox
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (491 reviews)
"We needed a bed for a quick crash session on the way through. The gentleman at the front desk was pleasant and so helpful and kind."
United States
Kyle
The price is S$98
includes taxes & fees
15 Jul - 16 Jul
Berkshire Travel Lodge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Property and hotel was very clean. The staff was pleasant and helpful."
Michael 1-night trip
Posted 12 hours ago
Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is S$86 per night from 2 Aug to 3 Aug
S$86
2 Aug - 3 Aug
includes taxes & fees
5.4/10 (852 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 The Yankee Inn and Berkshire Mountain Lodge. 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 Susan B. Anthony Birthplace Museum, Mount Greylock State Reservation Visitor Center and Skyline Trail. 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 17Ā°C, while the coldest months are January and February, with an average of -4Ā°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia