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Check prices for these dates

Tonight
19 Feb - 20 Feb
Tomorrow
20 Feb - 21 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

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Top hotels and accommodation in Windsor

Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (78)
"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 AU$237
includes taxes & fees
3 Mar - 4 Mar
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 AU$215
includes taxes & fees
20 Feb - 21 Feb
Becket Motel
Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (165)
"I rarely take the time to review anywhere I’ve stayed, but this place has stolen my heart! Its absolutely breathtaking property is second only to the friendliness of the staff. We couldn’t get enough of the sauna and hot tub with a view of the mountains, as well ans the evening firepit surrounded by andirondak chairs. The rooms and building is well maintained seemingly brand new. One of very few places I would stay again over and over! "
The price is AU$262
includes taxes & fees
10 Mar - 11 Mar
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)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is AU$305
includes taxes & fees
28 Feb - 1 Mar
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, (1002)
"We love this hotel! Our room was clean and spacious, the staff members we interacted with were friendly and helpful, the lobby/common and art galleries were very interesting, and there is so much to do within easy walking distance. "
The price is AU$220
includes taxes & fees
25 Feb - 26 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, (376)
"Lovely place to stay. Wonderful breakfast."
The price is AU$332
includes taxes & fees
25 Feb - 26 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 AU$448
includes taxes & fees
20 Feb - 21 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)
"room was clean heater was noisy bed was too soft pillow mattress no shampoo dont think they checked on our room after 1st night no coffee, cups room 101"
The price is AU$121
includes taxes & fees
20 Feb - 21 Feb
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Nice place. Made fresh waffle mix when I asked. No complaints"
The price is AU$148
includes taxes & fees
16 Mar - 17 Mar
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 AU$139
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, (703)
"Quiet "
The price is AU$109
includes taxes & fees
5 Mar - 6 Mar
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 AU$334
includes taxes & fees
23 Feb - 24 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, (585)
"It was close to Butternut on a snowy day. Very good for the value and what it is."
The price is AU$121
includes taxes & fees
20 Feb - 21 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 AU$438
includes taxes & fees
4 Mar - 5 Mar
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, (1000)
"Clean. Very nice location. Would be beautiful in the summer. Would go there again "
The price is AU$193
includes taxes & fees
2 Mar - 3 Mar
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, (595)
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"
The price is AU$231
includes taxes & fees
24 Feb - 25 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, (245)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is AU$233
includes taxes & fees
21 Feb - 22 Feb
Lakehouse Inn
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (627)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is AU$230
includes taxes & fees
23 Feb - 24 Feb
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (599)
"Great location. Pleasant staff."
The price is AU$121
includes taxes & fees
20 Feb - 21 Feb
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (713)
"spacious room. "
The price is AU$139
includes taxes & fees
20 Feb - 21 Feb
Howard Johnson by Wyndham Lenox
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, Ascend Hotel Collection, 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 Wahconah Falls State Park, Savoy Mountain State Forest and Mount Greylock State Reservation Visitor Center. You'll also find Mohawk Trail State Forest 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.