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Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
17 Jan - 19 Jan
Next weekend
24 Jan - 26 Jan

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Top hotels and accommodation in Windsor

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (402)
"Great! Love the coffee bar on each floor. "
The price is AU$337
includes taxes & fees
16 Jan - 17 Jan
The Williams Inn
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (475)
"This is a fantastic property. Excellent use of space in the rooms. Would highly recommend this establishment. "
The price is AU$160
includes taxes & fees
27 Jan - 28 Jan
Life House Berkshires
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1755)
"that was safe and clean good for relax"
The price is AU$348
includes taxes & fees
27 Jan - 28 Jan
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (723)
"Stayed at this Hotel, my kids and I loved it. It is very clean and comfortable place to stay. Thank you so much "
The price is AU$191
includes taxes & fees
24 Jan - 25 Jan
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Friendly, helpful management & staff. Excellent breakfast, made to order omelettes. Quiet. great pool & jacuzzi. Clean."
The price is AU$186
includes taxes & fees
27 Jan - 28 Jan
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (675)
"Nice warm place "
The price is AU$235
includes taxes & fees
20 Jan - 21 Jan
Hotel On North
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AU$335
includes taxes & fees
27 Jan - 28 Jan
Jiminy Peak Mountain Resort
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1001)
"The Hotel Downstreet is the best hotel. We always enjoy our stay here and never hesitate to stay again when in the area. "
The price is AU$210
includes taxes & fees
9 Feb - 10 Feb
Hotel Downstreet
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Nice pool and breakfast. Exactly like my previous experiences at Hampton Inn except this was probably the the fewest people I've encountered when staying with this chain. It was very quiet. Had the pool to ourselves for an hour."
The price is AU$229
includes taxes & fees
27 Jan - 28 Jan
Hampton Inn & Suites Berkshires-Lenox
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (419)
"Good"
The price is AU$300
includes taxes & fees
16 Jan - 17 Jan
Berkshire Mountain Lodge
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (544)
"Staff were pleasant and helpful. Limited menu at the hotel's bistro, but two restaurants across the busy road. Pool is much smaller than it looks in the photo and hot tub was too hot. Rooms somewhat small but well laid-out."
The price is AU$251
includes taxes & fees
10 Feb - 11 Feb
Courtyard by Marriott Lenox Berkshires
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Service was excellent. Very friendly front desk and breakfast staff. "
The price is AU$170
includes taxes & fees
20 Jan - 21 Jan
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (372)
"Our favorite place to stay. Rooms, amenities, service and breakfast are top notch. So close to great museums and restaurants. "
The price is AU$286
includes taxes & fees
12 Feb - 13 Feb
The Porches Inn at Mass MoCA
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (313)
"Stay was solid "
The price is AU$251
includes taxes & fees
20 Jan - 21 Jan
Fairfield Inn & Suites by Marriott Williamstown
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (623)
"Excellent place "
The price is AU$263
includes taxes & fees
16 Jan - 17 Jan
Hilton Garden Inn Lenox Pittsfield
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (497)
"The "
Club Wyndham Bentley Brook
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (760)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is AU$155
includes taxes & fees
15 Jan - 16 Jan
Berkshire Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (705)
"The room was clean and spacious. The parking lot still had a lot of snow and especially ice"
The price is AU$143
includes taxes & fees
15 Jan - 16 Jan
Howard Johnson by Wyndham Lenox
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (678)
"Very comfortable room in a lovely town! Easy check in and check out."
The price is AU$125
includes taxes & fees
16 Jan - 17 Jan
The Villager Motel
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (407)
"Historic Inn that is clean. If you are looking for something modern this is not for you. If you love a historic inn with all the old charm and character then this is your place. Staff was friendly and the bed comfortable. WiFi password provided upon picking up the room key. Internet worked well. Room was spacious for a family of 4."
The price is AU$171
includes taxes & fees
15 Jan - 16 Jan
1896 House Country Inn & Motels
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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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 Life House Berkshires and The Yankee, Trademark Collection by Wyndham. 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 Crane Museum of Papermaking, 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.