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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Windsor holiday rentals

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is Rp1.746.522
Rp2.135.138 total
includes taxes & fees
12 Jan - 13 Jan
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (988 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is Rp3.678.762
Rp4.109.178 total
includes taxes & fees
15 Jan - 16 Jan
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is Rp3.212.617
Rp3.588.493 total
includes taxes & fees
11 Jan - 12 Jan
Huttopia Berkshires
House (3 Bedrooms) | Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is Rp3.292.408
Rp9.299.877 total
includes taxes & fees
11 Jan - 12 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The staff were very nice, the room was clean and generally pleasant. the beds were not bad. They provide a continental-style breakfast, which is something. They are also dog-friendly! And there is a wonderful Indian restaurant that is adjacent to the hotel, and it is good! The only negative was a bit of mold, presumably causing some sinus issues, but that is to be expected in a hotel right on a lake like this. Otherwise, we would certainly stay there again."
Jonathan 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation Visitor Center. Adams Theater and Swift River are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.