Windsor Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Windsor hotels

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1005)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is €102
includes taxes & fees
19 Dec - 20 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Great stay!"
United States
Ann
The price is €60
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (803)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is €89
includes taxes & fees
30 Nov - 1 Dec
Berkshires Untold
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
The price is €81
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (972)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is €89
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (790)
"Place was great!"
United States
Benjamin
The price is €115
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is €158
includes taxes & fees
30 Nov - 1 Dec
The Cornell Inn, Lenox & The Berkshires
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (62)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is €92
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is €185
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1010)
"Staff was very nice!"
United States
David
The price is €103
includes taxes & fees
20 Dec - 21 Dec
Hotel Downstreet, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (768)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Desk, laptop workspace, blackout curtains, iron/ironing board
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, (1011)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is €86
includes taxes & fees
4 Dec - 5 Dec
Red Roof Inn PLUS+ South Deerfield – Amherst
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is €128
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Lobby sitting area
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, (1003)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is €90
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Berkshire Hills Inn & Suites
Suite, 2 Bedrooms
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (440)
"It is the perfect place to stay!"
United States
Darrell
The price is €166
includes taxes & fees
4 Dec - 5 Dec
The Porches Inn at Mass MoCA
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property – evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (544)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is €190
includes taxes & fees
30 Nov - 1 Dec
The Williams Inn
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (392)
"our stay was great."
United States
nathaniel
The price is €138
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Williamstown
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (762)
"It's very good for stay over"
United States
Frances
The price is €66
includes taxes & fees
1 Dec - 2 Dec
The Villager Motel
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (587)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is €117
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Lenox Berkshires
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

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Loved the lobby fireplace "
John 1-night trip
Posted 1 day ago
The Porches Inn at Mass MoCA

More cheap stays in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
The price is €86 per night from 4 Dec to 5 Dec
€86
4 Dec - 5 Dec
includes taxes & fees
7/10 Good! (1,011 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, Crane Museum of Papermaking and Mount Greylock State Reservation Visitor Center. You'll also find Skyline Trail and Swift River 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