Windsor Holiday Rentals

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Holiday Rentals in Windsor

Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

10.0 out of 10, Exceptional, (199)
"Nice place to stay. Ioved visiting covered bridges in area."
Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

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

9.8 out of 10, Exceptional, (44)
"Beautiful property "
The price is NZ$640
includes taxes & fees
21 Sept - 22 Sept
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.

Lovely Downtown Townhome

8.6 out of 10, Excellent, (91)
"We had a comfortable stay. Parking was the most challenging but it was fine too! "
The price is NZ$341
includes taxes & fees
23 Sept - 24 Sept
Lovely Downtown Townhome

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

10.0 out of 10, Exceptional, (122)
"This was a great overnight in a cute spot that we have seen along the higheay for years. Glad our fanily was finally able to check it out!"
The price is NZ$659
includes taxes & fees
22 Sept - 23 Sept
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Beautiful Boho Villa on Vine in the heart of Lancaster

9.6 out of 10, Exceptional, (38)
"Very clean and updated property, nestled in the heart of downtown with a short walk to great food, drinks and etc."
The price is NZ$555
includes taxes & fees
23 Sept - 24 Sept
Beautiful Boho Villa on Vine in the heart of Lancaster

"City Hideaway: Off-Grid Luxe"

2.0 star property
10.0 out of 10, Exceptional, (19)
"Perfect stay for our night in Lancaster. Everything was super clean and the truck was an amazing clever design. "
The price is NZ$301
includes taxes & fees
21 Sept - 22 Sept
"City Hideaway: Off-Grid Luxe"

1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

10.0 out of 10, Exceptional, (34)
"This was a cute little space that was perfect for our short stay and have everything that we needed."
The price is NZ$340
includes taxes & fees
2 Oct - 3 Oct
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

Waters Edge

10.0 out of 10, Exceptional, (135)
"Our stay was cut short but Brian and his wife were amazing host. We will definitely be returning "
Waters Edge

Spacious 5 bedroom home with large deck and hot tub

9.6 out of 10, Exceptional, (31)
"Had a great time. Communication with owner was excellent and timely."
Spacious 5 bedroom home with large deck and hot tub

Perfect family getaway with pool and hot tub close to everything!

9.8 out of 10, Exceptional, (82)
"It was close to the Sight & Sound theater and the Country Kettle Kitchen stores. The swimming pool and hot tub were very nice, but it should be noted that they are shared with the family and other guests. "
Perfect family getaway with pool and hot tub close to everything!

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

9.8 out of 10, Exceptional, (247)
"Beautiful, well cared for rental with a spectacular view."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

Unique tiny home experience in a one of a kind tiny home community!

9.4 out of 10, Exceptional, (17)
"It's a cute tiny home. Area is really nice and close to everything."
The price is NZ$266
includes taxes & fees
23 Sept - 24 Sept
Unique tiny home experience in a one of a kind tiny home community!

Restful and Quaint Cottage

9.8 out of 10, Exceptional, (123)
"It was a very restful place to visit.Very close to to many attractions...."
The price is NZ$587
includes taxes & fees
24 Sept - 25 Sept
Restful and Quaint Cottage

Log cabin nestled beside Chiques Creek in historic Lancaster County

9.4 out of 10, Exceptional, (116)
"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

Spacious Hilltop Escape with Basketball, Pingpong & Sunset Firepit

10.0 out of 10, Exceptional, (72)
"It was so nice to stay at this property. Plenty of room for our 7 member family. Loved the layout of the house. We even had a campfire one night. Nice and private too. Didn’t have to worry about neighbors right next door. Highly recommend staying at this vacation rental! "
Spacious Hilltop Escape with Basketball, Pingpong & Sunset Firepit

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

9.8 out of 10, Exceptional, (30)
"We had a great time and found the house well appointed for our needs. "
The price is NZ$551
includes taxes & fees
22 Sept - 23 Sept
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

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

2.0 star property
9.8 out of 10, Exceptional, (22)
"Cozy accommodations and quiet but bustling area! Definitely made the trip more enjoyable!! Would definitely stay again next time I’m in the area! "
The price is NZ$258
includes taxes & fees
21 Sept - 22 Sept
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

The Garden House

10.0 out of 10, Exceptional, (8)
"Lovely, cozy, vibrant home in a great part of the city. Lots of restaurants to walk to. Easy checkin and checkout process. Home had everything you needed."
The price is NZ$636
includes taxes & fees
20 Oct - 21 Oct
The Garden House

An adorable tiny home perfect for your tiny getaway!

9.8 out of 10, Exceptional, (21)
"So thankful I was able to stay in The Getaway Home. I grew to think of it as my home over my extended stay. Would recommend to others"
The price is NZ$267
includes taxes & fees
23 Sept - 24 Sept
An adorable tiny home perfect for your tiny getaway!

Inn the Barn

9.6 out of 10, Exceptional, (12)
"Inn the Barn was perfect - fun building, great decor, and every comfort we could have possibly needed. My tween/teen kids loved it, and we will definitely stay here again!"
Inn the Barn
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

Find out more about Windsor

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$258 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lovely Downtown Townhome: This holiday home rental outside of Windsor offers a garden, a selection of books and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.