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Check prices for these dates

Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Windsor holiday rentals

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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, (2170)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ₹9,396
₹11,486 total
includes taxes & fees
14 Dec - 15 Dec
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ₹15,372
₹17,170 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

The Ponds at Foxhollow
3.0 star property
Lenox
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
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, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ₹16,225
₹18,124 total
includes taxes & fees
15 Dec - 16 Dec
Jiminy Peak Mountain Resort
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Lovely little elegant hotel. Beautiful well appointed rooms. Comfortable bed. Reasonably price. Great find. "
Elizabeth 1-night trip
Posted 2 days ago
Berkshires Untold

Find out more about Windsor

Holiday Rentals in Windsor

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

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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 Wahconah Falls State Park. Crane Museum of Papermaking and Mount Greylock State Reservation Visitor Center 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.