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Top Holiday Rentals in Windsor

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

10.0 out of 10, Exceptional, (118)
"Loved our Shoe House stay! The house is adorable. The décor is super cute and comfortable. And the hosts have thought of everything to make your stay enjoyable. A fun, whimsical, and memorable experience for all ages. Many thanks!"
The price is £358
includes taxes & fees
4 Aug - 5 Aug
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Mountville Rental w/ Private Patio & Gas Grill!

9.8 out of 10, Exceptional, (13)
"We really enjoyed our stay. It was very go again clean and cozy. The host was exremley nice and friendly. Would definitly go again!"
Mountville Rental w/ Private Patio & Gas Grill!

2-bedroom 2nd Floor apartment in Mount Joy with off street parking

2.0 star property
9.6 out of 10, Exceptional, (17)
"Highly recommended!"
The price is £114
includes taxes & fees
30 Jul - 31 Jul
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

A working horse farm in Southern Lanc Co., nestled in Amish country.

2.0 star property
10.0 out of 10, Exceptional, (11)
"Beautiful place , peaceful, just a breathe of fresh air . They were great and responsive "
A working horse farm in Southern Lanc Co., nestled in Amish country.

Farmstay with pool and firepit

10.0 out of 10, Exceptional, (229)
"Very nice and quiet. The host were very helpful and we would stay again. "
Farmstay with pool and firepit

Lovely Downtown Townhome

8.6 out of 10, Excellent, (81)
"Beautiful place to stay to experience the city of Lancaster and still be close enough to enjoy the Amish country to. Thanks for letting us stay in your place for a few days!"
The price is £194
includes taxes & fees
25 Aug - 26 Aug
Lovely Downtown Townhome

Charming 2-bedroom cabin in lovely Lancaster County

6.6 out of 10, (4)
"We had a good stay."
Charming 2-bedroom cabin in lovely Lancaster County

The Loft at Riverside

9.6 out of 10, Exceptional, (24)
"Super clean, quiet, easy parking, feel like home, definitely will be back soon!"
The price is £151
includes taxes & fees
1 Aug - 2 Aug
The Loft at Riverside

Waters Edge

10.0 out of 10, Exceptional, (130)
"Beautiful scenery, Breath of fresh air. Very clean and comfortable. Very modern, we truly enjoyed our stay. Extra over the top amenities was a definite plus."
Waters Edge

Modern Farmhouse Getaway Close to Hershey

10.0 out of 10, Exceptional, (64)
"Excellent site for family stay. Many amenities and options to enjoy."
The price is £269
includes taxes & fees
30 Jul - 31 Jul
Modern Farmhouse Getaway Close to Hershey

Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.

9.8 out of 10, Exceptional, (40)
"Lovely property! It was beautifully decorated with lots of charm, thoughtful amenities (snacks!), and the beds were comfortable. We spent a lot of time in the hot tub and had a restful girls weekend. Would definitely stay again! "
The price is £284
includes taxes & fees
30 Jul - 31 Jul
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.

Modern 1-BR Apt by Train Station

9.4 out of 10, Exceptional, (3)
"Cozy and well-equipped apartment"
The price is £140
includes taxes & fees
30 Jul - 31 Jul
Modern 1-BR Apt by Train Station

Beautiful Boho Villa on Vine in the heart of Lancaster

9.6 out of 10, Exceptional, (34)
"Such a cool town, the property was close"
The price is £260
includes taxes & fees
30 Jul - 31 Jul
Beautiful Boho Villa on Vine in the heart of Lancaster

Calla Lily Farmhouse w/ Creekview by Nook

10.0 out of 10, Exceptional, (34)
"Was excellent for the family in be together in one place "
The price is £400
includes taxes & fees
12 Aug - 13 Aug
Calla Lily Farmhouse w/ Creekview by Nook

"City Hideaway: Off-Grid Luxe"

2.0 star property
10.0 out of 10, Exceptional, (17)
"Everything is fabulous. Cute & charming. Michelle was super friendly and was available if we needed her for anything. It is super clean and stocked. I'd give 10 stars if they let me! "
The price is £135
includes taxes & fees
4 Aug - 5 Aug
"City Hideaway: Off-Grid Luxe"

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

10.0 out of 10, Exceptional, (237)
"Nice, scenic location and very comfortable. It had everything we needed. We hope to come back again!"
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

The River Shack *kayaks*hottub*fishing*quiet*family

The price is £356
includes taxes & fees
4 Aug - 5 Aug
The River Shack *kayaks*hottub*fishing*quiet*family

Log cabin nestled beside Chiques Creek in historic Lancaster County

9.4 out of 10, Exceptional, (113)
"We loved our stay in this log cabin. The setting was beautiful, and the spacious cabin was furnished nicely, including with kitchenware. I had a number of questions before arrival, and the host's responses were quick and helpful. We wish we could have stayed longer!"
Log cabin nestled beside Chiques Creek in historic Lancaster County

River Rock Room at Muse House: Secluded Luxury in horse country.

9.8 out of 10, Exceptional, (258)
"Everything as promised and more! Beautiful place "
The price is £214
includes taxes & fees
3 Aug - 4 Aug
River Rock Room at Muse House: Secluded Luxury in horse country.

Wrightsville Cabin: Outdoor Fire Pit: Hammock by the creek: Long Level Marina

9.6 out of 10, Exceptional, (152)
"Just what we were seeking - quiet, secluded, comfortable place to enjoy winter delights."
Wrightsville Cabin: Outdoor Fire Pit: Hammock by the creek: Long Level Marina
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

Frequently asked questions

Can I find holiday rentals 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.

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

A working horse farm in Southern Lanc Co., nestled in Amish country. : This holiday home rental outside of Windsor is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Corn Cob Acres Field of Fun, or get out into nature at a spot like Rocky Ridge Park. Heritage Hill Golf Course and Moon Dancer Winery are a couple of places you'll find in the wider area.

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 such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.