Windsor Hotels

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Check prices for these dates

Tonight
6 Feb - 7 Feb
Tomorrow
7 Feb - 8 Feb
This weekend
7 Feb - 9 Feb
Next weekend
14 Feb - 16 Feb

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Top 10 trending Windsor hotels

Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (77)
"This waa our second stay at Bloomi g Inn and i hopw to stay again. I like being ablento walk to restaurants nearby. Cute shops too. "
The price is €137
includes taxes & fees
19 Feb - 20 Feb
Blooming Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is €131
includes taxes & fees
8 Feb - 9 Feb
Becket Motel
Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (161)
"Our stay was excellent! The hole stay was excellent… we will definitely spread our recommendations with friends and family! Look forward to our next stay there!"
The price is €144
includes taxes & fees
9 Feb - 10 Feb
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (127)
"Best place I have been. Beautiful place. Excellent host. "
The price is €173
includes taxes & fees
8 Feb - 9 Feb
The Trail in Adams - Berkshires’ Art Hotel
Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1001)
"The hotel was in a very walkable community. I enjoyed the galleries in the lobby and the art museum nearby."
The price is €127
includes taxes & fees
20 Feb - 21 Feb
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (374)
"The historical significance and what they have done to make it look like a rooming house for workers from the 1930's etc was done really well. Staff was nice and the breakfast was very organized and had good options. "
The price is €203
includes taxes & fees
9 Feb - 10 Feb
The Porches Inn at Mass MoCA
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is €267
includes taxes & fees
10 Feb - 11 Feb
Harbour House Inn
Pilgrim Inn
Individually decorated, individually furnished, desk, laptop workspace

Pilgrim Inn

2.5 star property
5.8 out of 10, (302)
"It is a good place and affordable. "
The price is €60
includes taxes & fees
7 Mar - 8 Mar
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"I especially liked the many amenities in the room…fridge,micro,control of heat,the quietness,nice breakfast and available hot beverages.very convenient to get to Stockbridge and Divine Mercy Shrine and very nice Big Y Grocery Store."
The price is €90
includes taxes & fees
23 Feb - 24 Feb
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...
The price is €86
includes taxes & fees
1 Mar - 2 Mar
Sunset Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (700)
"Stay was good as usual, other than a single person hanging out on balcony pacing back and forth making it uncomfortable room was clean other than food found left in microwave. Overall have had good stays and would keep booking"
The price is €74
includes taxes & fees
8 Feb - 9 Feb
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is €204
includes taxes & fees
9 Feb - 10 Feb
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (584)
"Was convenient and inexpensive. The back stairs were a little rickety. Also had to ring the bell to check in later in the evening, but was fine. Room was just the basics, but served the purpose for my one night stay. "
The price is €74
includes taxes & fees
8 Feb - 9 Feb
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is €300
includes taxes & fees
10 Feb - 11 Feb
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again. "
The price is €115
includes taxes & fees
11 Feb - 12 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (594)
"Room was clean and facility was nice"
The price is €141
includes taxes & fees
9 Feb - 10 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (242)
"The staff was very welcoming and courteous. Once you settled in you were offered a drink to help you relax from your travels(hot cider to take off the chill).Very pleasant cozy atmosphere The room was clean and inviting, The view of the lake amazing, We have been there twice once in the fall and again in winter. We will return."
The price is €142
includes taxes & fees
8 Feb - 9 Feb
Lakehouse Inn
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is €257
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (626)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is €140
includes taxes & fees
10 Feb - 11 Feb
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is €74
includes taxes & fees
8 Feb - 9 Feb
Wagon Wheel 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.
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Learn more about Windsor

Explore Windsor: its dining and more!

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Frequently asked questions

What's the best place to stay in Windsor?

Hotel Downstreet, located 13.6 mi (21.9 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 Vacation Village in the Berkshires and Life House Berkshires. See all available top hotels, or vacation rentals in Windsor.

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

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Windsor is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books 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 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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest. You'll also find Mount Greylock and Berkshire Museum 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.