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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Windsor hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is €121
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Wonderful place to stay"
The price is €119
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is €153
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1968)
"Beautiful location!"
The price is €111
includes taxes & fees
7 Sept - 8 Sept
Vacation Village in the Berkshires

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great location!"
The price is €137
includes taxes & fees
22 Sept - 23 Sept
Hotel Downstreet, Ascend Hotel Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is €155
includes taxes & fees
2 Sept - 3 Sept
The Cornell Inn, Lenox & The Berkshires

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (527)
"Great place , love it, will return"
The price is €142
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection

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

3.5 star property
9.0 out of 10, Wonderful, (704)
"Pleasant stay"
The price is €99
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is €228
includes taxes & fees
7 Sept - 8 Sept
The Red Lion Inn

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (587)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is €68
includes taxes & fees
7 Sept - 8 Sept
FairBridge Inn Express

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (863)
"Consistently a clean room with welcoming staff."
The price is €104
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (22)
"Really enjoyed my stay here, definitely need a car to get around"
The price is €129
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (436)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is €65
includes taxes & fees
14 Sept - 15 Sept
Berkshire Travel Lodge

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (867)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is €105
includes taxes & fees
24 Aug - 25 Aug
Howard Johnson by Wyndham Williamstown

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (729)
"Great quiet stay. "
The price is €85
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (625)
"It was lovely!"
The price is €61
includes taxes & fees
7 Sept - 8 Sept
Econo Lodge Lee - Great Barrington

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is €101
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Berkshire Hills Inn & Suites

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is €85
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"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 €102
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst
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

Learn more about Windsor

Explore Windsor: its dining and more!

Top Windsor Hotel 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 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 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.