Windsor Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Windsor

Vacation Village in the Berkshires
Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1933)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is S$170
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Set amidst lush greenery, this hotel complex offers a serene escape with pathways connecting its various buildings.

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (958)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is S$228
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort
Huttopia Berkshires
Situated in a lush forest, this cabin offers a serene retreat with a picnic table for outdoor dining or relaxation.

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (1)
"Huttopia Berkshires was wonderful! Very peaceful and a beautiful view. We enjoyed the on-site coffee shop/cafe and our tent with a deck and indoor plumbing! The staff was extremely friendly and helpful. The pool is lovely. Highly recommend!"
The price is S$141
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Steps lead down to the tranquil lake's edge, surrounded by trees and a rustic stone wall.

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."
Mitchell 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires

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. Mount Greylock and Barrington Stage Company 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.