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Check prices for these dates

Tonight
17 Jul - 18 Jul
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18 Jul - 19 Jul
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18 Jul - 20 Jul
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25 Jul - 27 Jul

Top Holiday Rentals in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1877)
"Great stay with all plenty of things to do…"
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is ₹13,846
₹15,465 total
includes taxes & fees
31 Jul - 1 Aug
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Huttopia Berkshires
Deluxe Tent | 2 bedrooms

Huttopia Berkshires

1.0 star property
Huttopia Berkshires
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

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. Bas Ridge Golf Course and Mount Greylock 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.