Windsor Holiday Rentals

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Holiday Rentals in Windsor

Lancaster Carriage House w/ Fireplace & Jacuzzi
10.0 out of 10, Exceptional, (1)
"The Carriage House was cozy and comfortable. The space is well stocked and designed for an extended stay. I didn't want to leave the next morning and will definitely bring my husband back here for a weekend getaway. "
United States
Holly H.
The price is NZ$275
includes taxes & fees
9 Nov - 10 Nov
Lancaster Carriage House w/ Fireplace & Jacuzzi
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
2.0 star property
9.8 out of 10, Exceptional, (27)
"Stayed here before, still great location for what I needed. Someone near me to it for the event in January:( Any time I head to PA, will be looking to stay here. "
United States
Jeffrey H.
The price is NZ$269
includes taxes & fees
9 Nov - 10 Nov
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
The Loft at Riverside
9.4 out of 10, Exceptional, (32)
"Super clean, quiet, easy parking, feel like home, definitely will be back soon!"
United States
Rey
The Loft at Riverside
"City Hideaway: Off-Grid Luxe"
2.0 star property
10.0 out of 10, Exceptional, (22)
"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! "
United States
Jodi
The price is NZ$312
includes taxes & fees
5 Nov - 6 Nov
"City Hideaway: Off-Grid Luxe"
Cozy Farm home near I83. Surrounded by a private park and hiking trails!
9.8 out of 10, Exceptional, (49)
"Love staying here for the location and the hosts provide a consistent quality each stay."
United States
William D.
The price is NZ$549
includes taxes & fees
9 Nov - 10 Nov
Cozy Farm home near I83. Surrounded by a private park and hiking trails!
Unique tiny home experience in a one of a kind tiny home community!
9.4 out of 10, Exceptional, (17)
"This was a nice tiny house. Very clean and easy to check in. Enjoyed a nice quiet little getaway and got to experience a tiny home in person. Would definitely stay here again."
United States
Brandon
The price is NZ$277
includes taxes & fees
5 Nov - 6 Nov
Unique tiny home experience in a one of a kind tiny home community!
The Quiet House on Main Street minutes from Everywhere
2.0 star property
The price is NZ$433
includes taxes & fees
16 Nov - 17 Nov
The Quiet House on Main Street minutes from Everywhere
A Cozy Getaway 5 min from the heart of Lancaster!
9.2 out of 10, Wonderful, (11)
"The house was perfect, they’ve made every convenience available for a smooth stay. "
United States
O'Delle H.
The price is NZ$347
includes taxes & fees
6 Nov - 7 Nov
A Cozy Getaway 5 min from the heart of Lancaster!
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
3.5 star property
The price is NZ$554
includes taxes & fees
5 Nov - 6 Nov
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
Cityside on North Prince, in Historic Downtown Lancaster
2.0 star property
9.8 out of 10, Exceptional, (18)
"The was in a great spot. The owner/host was "
United States
Leigh I.
The price is NZ$705
includes taxes & fees
6 Nov - 7 Nov
Cityside on North Prince, in Historic Downtown Lancaster
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
9.8 out of 10, Exceptional, (33)
"One of the cleanest houses we’ve ever stayed in! It was exactly as described. Perfect for a family trip to Hershey. We enjoyed some of the other nearby restaurants and attractions too, really couldn’t have asked for anything more. Looking forward to staying there again!! Thanks for sharing your home. "
United States
Keven S.
The price is NZ$598
includes taxes & fees
17 Nov - 18 Nov
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Sears Cottage Kit Home
2.0 star property
The price is NZ$290
includes taxes & fees
5 Nov - 6 Nov
Sears Cottage Kit Home
Quaint 1 bedroom apartment
9.4 out of 10, Exceptional, (40)
"The host was awesome to work with. And I definitely will stay again. "
United States
Michael B.
The price is NZ$214
includes taxes & fees
10 Nov - 11 Nov
Quaint 1 bedroom apartment
The Roundtop Chalet romantic couple’s getaway
9.8 out of 10, Exceptional, (11)
"So beautiful and relaxing"
United States
Christiana O.
The price is NZ$805
includes taxes & fees
13 Nov - 14 Nov
The Roundtop Chalet romantic couple’s getaway
Restful and Quaint Cottage
9.8 out of 10, Exceptional, (124)
"Loved the house and the fact it had everything you could need during your stay!"
United States
Kaci P.
The price is NZ$408
includes taxes & fees
5 Nov - 6 Nov
Restful and Quaint Cottage
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
9.8 out of 10, Exceptional, (48)
"It was clean, comfortable, and well-hosted!"
United States
Amy M.
The price is NZ$724
includes taxes & fees
6 Nov - 7 Nov
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
10.0 out of 10, Exceptional, (124)
"Amazing stay! Owners very polite."
United States
Amber C.
The price is NZ$711
includes taxes & fees
17 Nov - 18 Nov
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
The Sycamore Downtown Modern Home
9.6 out of 10, Exceptional, (76)
"Great convenient location. parking in rear. Nice ambiance. "
United States
duane
The price is NZ$691
includes taxes & fees
5 Nov - 6 Nov
The Sycamore Downtown Modern Home
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
10.0 out of 10, Exceptional, (5)
"The property is gorgeous and has all the necessary amenities! The host was quick to respond whenever we reached out! It was tucked away just enough but close enough to some restaurants and a winery. The only downside is the driveway is tricky, but the host gave us a tip & heads up before we arrived! Overall, it was a great spot and I’d definitely recommend it to others and come back again!"
United States
Amanda E.
The price is NZ$803
includes taxes & fees
12 Nov - 13 Nov
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
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

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$269 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?

Waters Edge: This holiday home rental outside of Windsor is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.