Windsor Holiday Rentals

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Holiday Rentals in Windsor

Cottage in Yorkana

10.0 out of 10, Exceptional, (126)
"Amazing stay! Owners very polite."
United States
Amber C.
The price is AU$615
includes taxes & fees
10 Dec - 11 Dec
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Holiday Home in Ross

8.6 out of 10, Excellent, (101)
"House was more spacious than we expected. It was well kept and in a fantastic location. My family had a wonderful trip!!!"
United States
Cardboard E.
The price is AU$294
includes taxes & fees
8 Dec - 9 Dec
Lovely Downtown Townhome

Cottage in Conestoga

9.8 out of 10, Exceptional, (124)
"We loved staying in this cottage. It is in a quiet location. Loved the hot tub. "
United States
Anonymous traveller
The price is AU$402
includes taxes & fees
3 Dec - 4 Dec
Restful and Quaint Cottage

Holiday Home in Lancaster

9.4 out of 10, Exceptional, (38)
"Nice location for visit the Lancaster area!"
United States
Bill S.
The price is AU$290
includes taxes & fees
20 Dec - 21 Dec
The Loft at Riverside

Cottage in Lancaster

9.8 out of 10, Exceptional, (91)
"We enjoyed our stay and would recommend! Host is very helpful and location was great. "
United States
Kara S.
Perfect family getaway with pool and hot tub close to everything!

Cabin in Marietta

10.0 out of 10, Exceptional, (247)
"The cabin had everything we needed.The very friendly goats made the stay extra fun."
United States
Lisa G.
Farmstay with pool and firepit

Holiday Home in Willow Street

9.8 out of 10, Exceptional, (269)
"Very comfortable and cozy place that stay! "
United States
Terri H.
The price is AU$436
includes taxes & fees
2 Dec - 3 Dec
River Rock Room at Muse House: Secluded Luxury in horse country.

Holiday Home in Lancaster

5,100 Sq Ft Mansion w/ Firepit & Grill Near Sight & Sound In Lancaster

Holiday Home in Pequea

10.0 out of 10, Exceptional, (141)
"Beautiful house and property that my extended family consisting of 14 people (ranging from ages 8 to 81) thoroughly enjoyed. Just bring your own groceries and the kitchen is stocked with everything else anyone could need. My brother-in-law brought his own kayaks and body boards so we could explore the river and tiny island across from the property. Brian was a great host; always available to answer all of our questions (and we had a lot) about the house and things to do in the area."
United States
Nicole K.
Waters Edge

Cabin in Wrightsville

9.6 out of 10, Exceptional, (158)
"We have been around for a bit and this is still one of our favorite places to stay. It’s just…. A little bridge to relaxation. The check I. Situation is very easy and the check out part is almost nonexistent. This place is a steal. "
United States
Adam W.
Wrightsville Cabin: Outdoor Fire Pit: Hammock by the creek: Long Level Marina

Holiday Home in New Providence

10.0 out of 10, Exceptional, (49)
"Add a wonderful stay with my family."
United States
Sheryl P.
Historic Stone House on Beaver Creek

Apartment in Lancaster

10.0 out of 10, Exceptional, (2)
"Lovely, clean, and comfortable accommodations!Perfect location, would definitely stay here again!"
United States
Diane C.
The price is AU$188
includes taxes & fees
2 Dec - 3 Dec
15 Minutes To Sight & Sound Near Downtown Lancaster w/ Firepit

Holiday Home in Stadium District

2.0 star property
9.8 out of 10, Exceptional, (20)
"Great place, very well appointed and very stylish decor. "
United States
thomas b.
The price is AU$621
includes taxes & fees
2 Dec - 3 Dec
Cityside on North Prince, in Historic Downtown Lancaster

Holiday Home in Manheim

9.8 out of 10, Exceptional, (39)
"Great location and accommodations! Would definitely stay again! "
United States
Louis R.
The price is AU$857
includes taxes & fees
7 Dec - 8 Dec
Calla Lily Farmhouse w/ Creekview by Nook

Holiday Home in Lancaster

2.0 star property
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay at the Red Rose Cottage. The place was updated and very warm and inviting. There's plenty of room for everyone, and we will stay here once we visit this area again."
United States
Matt K.
Historic 3 Bedroom 1875 Farmhouse 1 Mile from Lancaster City, Sleeps 8

Holiday Home in Millersville

10.0 out of 10, Exceptional, (75)
"The accommodations exceeded our expectations- the place is updated and well maintained, and had everything we needed."
United States
Kimberly W.
Private home has WIFI, Fireplace, Fire pit, Full Kitchen, 4 mile from Lancaster!

Holiday Home in Lancaster

9.0 out of 10, Wonderful, (18)
"Lovely home. Very clean and had everything we needed."
United States
Chizara N.
Cozy Lancaster County Retreat: 3 Bedroom, 2 Full Bath w/ AC, WiFi, and Fire Pit

Cottage in Willow Street

10.0 out of 10, Exceptional, (208)
"A superb property - exceptionally clean and very well equipped with everything you could possibly need! The location was perfect for exploring the local area and further afield and the hot tub was an added bonus for relaxing in the evenings."
United Kingdom
Gillian P.
Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

Holiday Home in Mount Joy

10.0 out of 10, Exceptional, (46)
"This property was great. Very well furnished with an amazing game room. "
United States
David O.
Resort Pickleball Pool Hot Tub Theater Arcade Golf

Holiday Home in Pequea

9.8 out of 10, Exceptional, (284)
"We loved the spacious rooms. We used the hot tub every night. The view from this property is so serene and relaxing. 100% recommend!"
United States
Carrie D.
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
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 favourite 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 depend 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 AU$188 per night. Entering your travel dates in the search wizard might find you 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 Field of Screams, or get out into nature at a spot like Rocky Ridge Park. Heritage Hill Golf Course and AvalancheXpress 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.