A rustic barn surrounded by autumn foliage and a field.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Windsor holiday rentals

Front of property

Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,513
HK$2,512 total
includes taxes & fees
5 Aug - 6 Aug
Bristol Condo Near Espn HQ & Lake Compounce!
Living area

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is HK$3,666
HK$5,335 total
includes taxes & fees
30 Jul - 31 Jul
Newly Renovated 2 floor Getaway
Living area

Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
The price is HK$1,517
HK$2,372 total
includes taxes & fees
30 Jul - 31 Jul
Trumbull Apartments
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

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

10/10 Excellent
"The proximity to the airport is wonderful for the price. The staff are very pleasant, and the rooms are comfortable and clean. For an economical stay, it is highly recommended."
Tiffany 3-night trip
Posted 2 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! 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 holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Windsor Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What are some of the best holiday rentals that Windsor has to offer?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated holiday home rental in Windsor has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Windsor?

Expedia has 7 holiday rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Historical Society and Oliver Ellsworth Homestead, whereas Keney Park and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Windsor Arts Center and Loomis Chaffee School.

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 feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.