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Top hotels and accommodation in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1005)
"It’s the only place close to the Treehouse so we stayed there, it is definitely a RR Inn."
The price is AU$159
includes taxes & fees
11 Sept - 12 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is AU$226
includes taxes & fees
22 Sept - 23 Sept
Blooming Inn

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (735)
"Great quiet stay. "
The price is AU$152
includes taxes & fees
9 Sept - 10 Sept
The Villager Motel

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (621)
"Very clean place for a very good price "
The price is AU$359
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Lovely setting on the lake."
The price is AU$216
includes taxes & fees
14 Sept - 15 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (64)
"Chris was great!"
The price is AU$166
includes taxes & fees
9 Sept - 10 Sept
The Springs Motel

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (945)
"Comfortable, clean, and great continental breakfast options! "
The price is AU$152
includes taxes & fees
9 Sept - 10 Sept
Willows Motel Williamstown

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (292)
"This motel is a good value considering the location and condition. Simple motel that is fairly dated. Very friendly owners/staff. If you are looking for a basic motel that is not expensive, is clean and convenient to Williamstown, this a good fit."
The price is AU$149
includes taxes & fees
11 Sept - 12 Sept
Williamstown Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Very nice stay"
The price is AU$181
includes taxes & fees
11 Sept - 12 Sept
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is AU$288
includes taxes & fees
21 Sept - 22 Sept
Element Lenox Berkshires

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1005)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is AU$259
includes taxes & fees
11 Sept - 12 Sept
Hotel Downstreet, an Ascend Collection Hotel

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (851)
"We really enjoyed our time at Cozy Corner Motel. 100% recommended "
The price is AU$152
includes taxes & fees
14 Sept - 15 Sept
Cozy Corner Motel

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (800)
"My stay was perfect. I can't wait to stay there again. "
The price is AU$135
includes taxes & fees
9 Sept - 10 Sept
Howard Johnson by Wyndham Lenox

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (573)
"Excellent place. Bountiful view. "
The price is AU$213
includes taxes & fees
9 Sept - 10 Sept
Maple Terrace Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (36)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is AU$241
includes taxes & fees
10 Sept - 11 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Revival House

3.0 star property
8.6 out of 10, Excellent, (14)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is AU$307
includes taxes & fees
9 Sept - 10 Sept
The Revival House

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is AU$277
includes taxes & fees
9 Sept - 10 Sept
The Cornell Inn, Lenox & The Berkshires

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is AU$167
includes taxes & fees
10 Sept - 11 Sept
Huttopia Berkshires

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Staff was excellent. Clean room and facility. location is convenient to many Berkshire attractions "
The price is AU$245
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn & Suites Berkshires-Lenox

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (870)
"Consistently a clean room with welcoming staff."
The price is AU$186
includes taxes & fees
11 Sept - 12 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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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Top Windsor Hotel Reviews

More cheap accommodation in Windsor

More cheap accommodation in Windsor

Explore a world of travel with Expedia

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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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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.