Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

9.4 out of 10, Exceptional, (9 reviews)
"Lovely, clean, and comfortable accommodations!Perfect location, would definitely stay here again!"
United States
Diane C.
The price is AU$190
includes taxes & fees
8 Mar - 9 Mar
15 Minutes To Sight & Sound Near Downtown Lancaster w/ Firepit
10.0 out of 10, Exceptional, (75 reviews)
"Everything was wonderful, from the location to the house!"
United States
Amelia F.
The price is AU$404
includes taxes & fees
8 Mar - 9 Mar
Modern Farmhouse Getaway I 2 BR, Sleeps up to 6
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Cute property!"
United States
Becky R.
The price is AU$237
includes taxes & fees
8 Mar - 9 Mar
Lancaster Carriage House w/ Fireplace & Jacuzzi
9.2 out of 10, Wonderful, (11 reviews)
"The house was perfect, they’ve made every convenience available for a smooth stay. "
United States
O'Delle H.
The price is AU$278
includes taxes & fees
8 Mar - 9 Mar
A Cozy Getaway 5 min from the heart of Lancaster!

Holiday Home in Chestnut Hill

The Garden House
9.8 out of 10, Exceptional, (10 reviews)
"A cheerful, unique little house in historic district. Sparkling clean, beautifully decorated, everything you need is provided, smooth entry, great host communication. Would stay again in a heartbeat!"
United States
Nancy D.
The price is AU$410
includes taxes & fees
9 Mar - 10 Mar
The Garden House

Cottage in Conestoga

Restful and Quaint Cottage
9.8 out of 10, Exceptional, (128 reviews)
"This place is fantastic, the neighborhood is quiet, clean, and beautiful. The cottage was clean, cozy, and fully equipped. Definitely, I would love to go back again."
United States
Danna C.
The price is AU$393
includes taxes & fees
9 Mar - 10 Mar
Restful and Quaint Cottage
9.8 out of 10, Exceptional, (34 reviews)
"Host communication was great! Instructions for check in and check out were easy to read and follow. There were plenty of supplies, place was clean and cozy. Price was reasonable and hope to stay again in future visit!"
United States
Dora F.
The price is AU$377
includes taxes & fees
9 Mar - 10 Mar
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
9.8 out of 10, Exceptional, (44 reviews)
"This was a beautiful home for our weekend girls trip. The house was clean with a modern vibe. Lots of extra touches that went above and beyond (k-cups for morning coffee win!). Host was very responsive and helpful with suggested restaurants etc. Will definitely stay here again when visiting Lancaster in the future. "
United States
Jennifer B.
The price is AU$400
includes taxes & fees
9 Mar - 10 Mar
Getaway on Grant, heart of Downtown with parking
9.4 out of 10, Exceptional, (3 reviews)
"Great location close to everything downtown, Peter was very responsive when we reached out with questions. "
United States
Andy L.
The price is AU$276
includes taxes & fees
11 Mar - 12 Mar
The Church Street Suite - Downtown, Cozy, Parking
10.0 out of 10, Exceptional, (44 reviews)
"This has been our 4th stay and as always it was top notch."
United States
Bradley K.
The price is AU$279
includes taxes & fees
10 Mar - 11 Mar
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
9.8 out of 10, Exceptional, (15 reviews)
"Enjoyed our stay, plenty to do in the neighborhood and walkable to downtown."
United States
Ted S.
The price is AU$370
includes taxes & fees
9 Mar - 10 Mar
Comfy renovated townhome - heart of Downtown Lancaster
9.6 out of 10, Exceptional, (37 reviews)
"Excelente"
Mexico
Jairo
The price is AU$427
includes taxes & fees
10 Mar - 11 Mar
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Holiday Home in Historic Downtown Lancaster

Beautiful Boho Villa on Vine in the heart of Lancaster
9.4 out of 10, Exceptional, (51 reviews)
"Access to the house was easy and simple. Street parking was never a hassle. The location was great to be able to walk everywhere downtown."
United States
Steven A. S.
The price is AU$430
includes taxes & fees
9 Mar - 10 Mar
Beautiful Boho Villa on Vine in the heart of Lancaster

Holiday Home in Pequea

Enola Trail Getaway *bikes*rural
10.0 out of 10, Exceptional, (3 reviews)
"I had a great time and the place was very beautiful and peaceful "
United States
Brittany R.
The price is AU$600
includes taxes & fees
8 Mar - 9 Mar
Enola Trail Getaway *bikes*rural
9.6 out of 10, Exceptional, (14 reviews)
"Two night stay was very nice. Great living, kitchen and bedroom spaces. Very quiet area."
United States
Rene S.
The price is AU$487
includes taxes & fees
6 Mar - 7 Mar
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.
9.4 out of 10, Exceptional, (24 reviews)
"It was a lovely place to stay that was close to Hershey where we were visiting."
United States
Karin B.
The price is AU$228
includes taxes & fees
8 Mar - 9 Mar
An adorable tiny home perfect for your tiny getaway!
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay all in all"
United States
Mary C.
The price is AU$325
includes taxes & fees
9 Mar - 10 Mar
Don't miss this Cute, Quaint Brick Cottage which is is located in York, PA.
9.0 out of 10, Wonderful, (6 reviews)
"Nicely remodeled place."
United States
Didier S.
The price is AU$261
includes taxes & fees
11 Mar - 12 Mar
Modern Downtown Lancaster Apt – Walk to Train & Amtrak

Holiday Home in Ross

Lovely Downtown Townhome
8.8 out of 10, Excellent, (110 reviews)
"The host was kind and the home was very clean and fit our needs perfectly!"
United States
Emily J.
The price is AU$293
includes taxes & fees
9 Mar - 10 Mar
Lovely Downtown Townhome
9.6 out of 10, Exceptional, (21 reviews)
"Our first impression of the property was WOW! It was very functional and it was great for a short stay. Very quiet and peaceful stay. "
United States
Kristen T.
The price is AU$226
includes taxes & fees
8 Mar - 9 Mar
Unique tiny home experience in a one of a kind tiny home community!
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$221 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.