Search 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
22 Apr - 23 Apr
Tomorrow
23 Apr - 24 Apr
This weekend
24 Apr - 26 Apr
Next weekend
1 May - 3 May

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windsor hotels

Reception

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,008 reviews)
"Comfy bed, nice front desk staff."
United States
Christina
The price is AU$153
includes taxes & fees
27 Apr - 28 Apr
Red Roof Inn PLUS+ South Deerfield – Amherst
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is AU$179
includes taxes & fees
23 Apr - 24 Apr
The Yankee Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is AU$167
includes taxes & fees
11 May - 12 May
Quality Inn Lee - Lenox South
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean and cozy room, friendly staff, and fresh fruit for breakfast. Great location right next to Williams College."
United States
Phebe
The price is AU$126
includes taxes & fees
23 Apr - 24 Apr
Willows Motel Williamstown
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, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is AU$123
includes taxes & fees
30 Apr - 1 May
Howard Johnson by Wyndham Lenox
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is AU$123
includes taxes & fees
30 Apr - 1 May
The Villager Motel
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,001 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is AU$158
includes taxes & fees
27 Apr - 28 Apr
Best Western Plus Berkshire Hills Inn & Suites
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is AU$234
includes taxes & fees
23 Apr - 24 Apr
Blooming Inn
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is AU$298
includes taxes & fees
30 Apr - 1 May
UU Rowe Camp and Conference Center
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (899 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is AU$130
includes taxes & fees
30 Apr - 1 May
Cozy Corner Motel
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is AU$233
includes taxes & fees
28 Apr - 29 Apr
The Revival House
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (908 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is AU$152
includes taxes & fees
3 May - 4 May
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AU$235
includes taxes & fees
28 Apr - 29 Apr
Element Lenox Berkshires
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
The price is AU$162
includes taxes & fees
26 Apr - 27 Apr
Maple Terrace Motel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (908 reviews)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is AU$156
includes taxes & fees
26 Apr - 27 Apr
Howard Johnson by Wyndham Williamstown
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,335 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is AU$149
includes taxes & fees
29 Apr - 30 Apr
Vacation Village in the Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is AU$158
includes taxes & fees
5 May - 6 May
Shaker Mill Inn
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Very clean, modern hotel. Would definitely stay here again. "
United States
Debra
The price is AU$200
includes taxes & fees
30 Apr - 1 May
Hampton Inn & Suites Berkshires-Lenox
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AU$109
includes taxes & fees
23 Apr - 24 Apr
Pleasant Valley Motel West Stockbridge
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (674 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AU$207
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Lenox Pittsfield
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

Recent Reviews in Windsor

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

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

10/10 Excellent
"Decent "
Holly 6-night trip
Posted 15 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap accommodation in Windsor

Berkshire Inn

Berkshire Inn

150 W Housatonic St Pittsfield MA
The price is AU$121 per night from 3 May to 4 May
AU$121
3 May - 4 May
includes taxes & fees
7.8/10 Good! (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 Hotel Downstreet, an Ascend Collection Hotel 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?
Peace and quiet on the lake: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. 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, Susan B. Anthony Birthplace Museum and Mount Greylock State Reservation Visitor Center. 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