A sunset over a calm lake with vibrant orange and blue skies.

Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

Walnut Street Retreat Downtown, Dog Friendly

Walnut Street Retreat Downtown, Dog Friendly
3.5 star property
Windsor
The price is S$545
includes taxes & fees
27 Jul - 28 Jul
Walnut Street Retreat Downtown, Dog Friendly

Family-friendly Townhome ~ 2 Mi to Windsor Lake!

Family-friendly Townhome ~ 2 Mi to Windsor Lake!
3.5 star property
Windsor
8.0 out of 10, Very good, (2 reviews)
"Our stay was absolutely fantastic. The house was impeccably clean, which my OCD LOVED. This house was exactly as described. It truly was a home away from home. Everyone kept commenting on how much they loved the kitchen and the space. The hosts were very responsive, and provided all the necessities of home. "
United States
Kenzey
The price is S$881
includes taxes & fees
19 Jul - 20 Jul
Family-friendly Townhome ~ 2 Mi to Windsor Lake!

Chimney Park Retreat King Suite + Fenced Yard

Chimney Park Retreat King Suite + Fenced Yard
3.5 star property
Windsor
The price is S$590
includes taxes & fees
6 Jul - 7 Jul
Chimney Park Retreat King Suite + Fenced Yard

Oak Haus Group Stay w/ Fenced Yard & Game Room

Oak Haus Group Stay w/ Fenced Yard & Game Room
3.5 star property
Windsor
The price is S$756
includes taxes & fees
7 Jul - 8 Jul
Oak Haus Group Stay w/ Fenced Yard & Game Room

Windshire Retreat Pool, Garage & Pet-friendly

Windshire Retreat Pool, Garage & Pet-friendly
3.5 star property
Windsor
The price is S$803
includes taxes & fees
3 Aug - 4 Aug
Windshire Retreat Pool, Garage & Pet-friendly

The Wandering Key Gather & Unwind, Sleeps 14

The Wandering Key Gather & Unwind, Sleeps 14
3.5 star property
Windsor
The price is S$1,103
includes taxes & fees
12 Jul - 13 Jul
The Wandering Key Gather & Unwind, Sleeps 14

Windsor Farmhouse Family Fun, Yard & Fireplace

Windsor Farmhouse Family Fun, Yard & Fireplace
4.0 star property
Windsor
The price is S$727
includes taxes & fees
7 Jul - 8 Jul
Windsor Farmhouse Family Fun, Yard & Fireplace

New! Family-friendly Home w/ Pool Table, King Beds

New! Family-friendly Home w/ Pool Table, King Beds
4.0 star property
Windsor
The price is S$1,051
includes taxes & fees
6 Jul - 7 Jul
New! Family-friendly Home w/ Pool Table, King Beds
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

Top Windsor Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Karen Suman Park, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its zoo.

How many holiday rentals will I find in Windsor?

Choose from 56 Expedia holiday rentals in Windsor for a memorable holiday.

What’s there to see and do in Windsor?

Windsor Lake and Cache La Poudre River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Karen Suman Park. Other places in town to visit include Pelican Lakes Golf & Country Club and Hunters Moon Meadery.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.