Default HTG hotel image

Windsor Hotels

  • 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

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

Room
Business centre
Standard Room, 1 King Bed, Non Smoking
Breakfast area

1. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
ERICIA
€59
includes taxes & fees
30 Aug - 31 Aug
FairBridge Inn Express
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Property amenity
Exterior
Room

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Jermaine
€110
includes taxes & fees
20 Sept - 21 Sept
Best Western Plus Berkshire Hills Inn & Suites
Standard Room, 1 King Bed, Non Smoking
Standard Room, 1 King Bed, Non Smoking
Room
Exterior

3. Rodeway Inn

Rodeway Inn
Adams
United States
Andrew
€69
includes taxes & fees
9 Sept - 10 Sept
Rodeway Inn
Room
Property grounds
Pool
Property grounds

4. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Adriana
€86
includes taxes & fees
27 Aug - 28 Aug
Berkshire Inn
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub
Living area
View from room
Superior Room, 1 King Bed, Jetted Tub

5. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
€146
includes taxes & fees
13 Sept - 14 Sept
The Yankee Inn
Living area
Games room
Front of property
Reception

6. The Revival House

The Revival House
Adams
United States
James
€158
includes taxes & fees
31 Aug - 1 Sept
The Revival House
Courtyard
Cabin, 3 Bedrooms, Mountainside | Living area
Breakfast meal
Honeymoon Suite, 1 King Bed, Patio

7. The Springs Motel

The Springs Motel
New Ashford
United States
Shakeila
€115
includes taxes & fees
31 Aug - 1 Sept
The Springs Motel
Pool
Reception
Exterior
Breakfast meal

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ken
€114
includes taxes & fees
24 Sept - 25 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Room
Room
Exterior
Pool

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Myrna
€114
includes taxes & fees
23 Sept - 24 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Room
Property amenity
Lobby
Exterior

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Sheila
€76
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox
Lobby
Property entrance
Lobby
Pool

11. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
€110
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Room
Reception
Exterior
Front of property

12. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Victoria
€142
includes taxes & fees
2 Sept - 3 Sept
Hotel Downstreet, an Ascend Collection Hotel
Breakfast area
Pool
Exterior
Snack bar

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
€122
includes taxes & fees
9 Sept - 10 Sept
Hampton Inn & Suites Berkshires-Lenox
Exterior
Living area
Living area
Deluxe Double Suite- NO PETS ALLOWED

14. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
€95
includes taxes & fees
30 Aug - 31 Aug
The Central Downtown Inn & Suites
Gazebo
Reception
Standard Room, 1 Queen Bed, Non Smoking
Front of property

15. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jeremy
€89
includes taxes & fees
9 Sept - 10 Sept
Cozy Corner Motel
Exterior
Garden
Living area
View from property

16. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
€230
includes taxes & fees
27 Aug - 28 Aug
Harbour House Inn
Lobby lounge
Lobby
Interior
Lobby

17. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
€136
includes taxes & fees
7 Sept - 8 Sept
Berkshires Untold
Property grounds
Property grounds
Exterior
Room

18. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Richard
€99
includes taxes & fees
27 Aug - 28 Aug
Willows Motel Williamstown
Lobby
Standard Room, 1 King Bed, Non Smoking
Standard Room, 1 King Bed, Non Smoking
Lobby

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
€105
includes taxes & fees
15 Sept - 16 Sept
Quality Inn Lee - Lenox South
Property entrance
Lobby sitting area
Lobby
Library Suite, 1 King Bed

20. Hotel On North

Hotel On North
Pittsfield
United States
Drew
€171
includes taxes & fees
7 Sept - 8 Sept
Hotel On North
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This particular room, the mattress on the sifabed is worn and uncomfortable. Needs a real topper, or to be replaced. I slept on the couch, not in the bed, with a sheet on it."
marsha 4-night trip
Posted 10 hours ago
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"My wife and I really enjoyed our stay. It was quiet and clean. Really liked that there was a Stop and Shop right across the street."
Randal L 2-night trip
Posted 15 hours ago
Berkshire Mountain Lodge
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"We have been coming for the last few years. Generally, 4 or 5 times a year. We love the Berkshires. People vote with their feet. It is a good value. We will be back."
Andrew 1-night trip
Posted 20 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."
Barb 1-night trip
Posted 1 day ago
The Yankee Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Fine place to stay in the Lenox area."
Anthony 1-night trip
Posted 1 day ago
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."
Robert 3-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 4 days ago
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
€59
30 Aug - 31 Aug
includes taxes & fees
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
€76
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (903 reviews)
Howard Johnson by Wyndham Lenox
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
€95
7 Sept - 8 Sept
includes taxes & fees
Red Roof Inn PLUS+ South Deerfield – Amherst
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
€110
20 Sept - 21 Sept
includes taxes & fees
8.4/10 Very good! (1,012 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
€114
24 Sept - 25 Sept
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
€146
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,021 reviews)
The Yankee Inn

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.
What are some of the best holiday rentals that Windsor has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Windsor is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease 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 garden and a selection of games. 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 Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center and Pontoosuc Lake. You'll also find Swift River and Mount Greylock 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.

Explore a world of travel with Expedia