Search Windsor hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Aug - 19 Aug
Tomorrow
19 Aug - 20 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout curtains, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1004)
"Friendly staff and good place for the price. You get everything you need, is clean and close to dinning/shopping. I recommend it. "
The price is NZ$202
includes taxes & fees
21 Aug - 22 Aug
Red Roof Inn PLUS+ South Deerfield – Amherst
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is NZ$277
includes taxes & fees
14 Sept - 15 Sept
Blooming Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Lovely setting on the lake."
The price is NZ$239
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is NZ$185
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (939)
"Comfortable, clean, and great continental breakfast options! "
The price is NZ$168
includes taxes & fees
1 Sept - 2 Sept
Willows Motel Williamstown
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (682)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NZ$302
includes taxes & fees
24 Aug - 25 Aug
Berkshires Untold
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Great staff! Comfortable bed! "
The price is NZ$271
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Berkshires-Lenox
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (728)
"Great quiet stay. "
The price is NZ$168
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.0 out of 10, Wonderful, (11)
"Self check in was easy. Rooms were spacious and clean. Great place."
The price is NZ$340
includes taxes & fees
19 Aug - 20 Aug
The Revival House
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (408)
"Very comfortable room that worked great for our family. "
The price is NZ$373
includes taxes & fees
16 Sept - 17 Sept
The Porches Inn at Mass MoCA
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is NZ$307
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
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, (1005)
"Great location!"
The price is NZ$271
includes taxes & fees
16 Sept - 17 Sept
Hotel Downstreet, Ascend Hotel Collection
Element Lenox Berkshires
Free daily continental breakfast

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is NZ$287
includes taxes & fees
1 Sept - 2 Sept
Element Lenox Berkshires
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (846)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is NZ$186
includes taxes & fees
3 Sept - 4 Sept
Cozy Corner Motel
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (570)
"Fabulous place"
The price is NZ$287
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (571)
"The staff, room and property was wonderful! "
The price is NZ$212
includes taxes & fees
2 Sept - 3 Sept
Maple Terrace Motel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (576)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (18)
"Really enjoyed my stay here, definitely need a car to get around"
The price is NZ$255
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (485)
"The property was spacious but still had a cozy feel. "
The price is NZ$435
includes taxes & fees
15 Sept - 16 Sept
The Williams Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is NZ$207
includes taxes & fees
1 Sept - 2 Sept
Quality Inn
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Windsor

Explore Windsor: its dining and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Liked the fact there are 2 pools, an indoor and an outdoor."
MARK 2-night trip
Posted 14 hours ago
Vacation Village in the Berkshires

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.

What are some of the best holiday rentals that Windsor has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself 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 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 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.