Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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

2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Mount Joy
9.8 out of 10, Exceptional, (32 reviews)
"Spacious, comfortable beds, convenient to restaurants, great price, 5 minutes to Spooky Nook. Clean, nice towels. Host left some drinks and snacks. I definitely recommend. We will be back."
United States
Kimberly
The price is AU$219
includes taxes & fees
10 June - 11 June
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market
3.0 star property
York
The price is AU$545
includes taxes & fees
10 June - 11 June
Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market
York
7.2 out of 10, Good, (5 reviews)
"House was in a good, central location. Cute home. Nice, comforting touches to the house. Beds were comfortable. "
United States
Melissa
The price is AU$543
includes taxes & fees
10 June - 11 June
Work & Play! Home 1 Mi to Dtwn & Central Market

Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (39 reviews)
"My family had a wonderful stay at this Pennsylvania home! The house was extremely clean, beautifully decorated, and very comfortable. It had everything we needed during our stay, and you can tell the owners put a lot of thought into making guests feel welcome. We truly enjoyed our time there and would definitely stay again. Highly recommend!"
United States
Jodi
The price is AU$415
includes taxes & fees
7 June - 8 June
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

Restful and Quaint Cottage

Restful and Quaint Cottage
Conestoga
9.8 out of 10, Exceptional, (132 reviews)
"My husband and I had such a wonderful stay here. Kevin was an excellent host who promptly responded to any questions we had. The cabin itself was beautiful and well maintained and was nestled in such a peaceful area. The hot tub was definitely an added bonus with such beautiful scenery! We would highly recommend a stay here and hope to stay here again ourselves!"
United States
Maureen H.
The price is AU$390
includes taxes & fees
8 June - 9 June
Restful and Quaint Cottage

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6
Elizabethtown
10.0 out of 10, Exceptional, (83 reviews)
"The house was wonderful, great spaces, very well equipped and decorated. The host was very kind and attentive to our needs throughout the stay. The area is rural and provides a quiet and beautiful backdrop for your adventure or getaway."
United States
Brian J.
Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

The Pop Loft | Downtown Lancaster

The Pop Loft | Downtown Lancaster
West End
The price is AU$362
includes taxes & fees
10 June - 11 June
The Pop Loft | Downtown Lancaster

Quaint -2-bedroom house in Lancaster with cool AC breeze

Quaint -2-bedroom house in Lancaster with cool AC breeze
Prospect Heights
8.0 out of 10, Very good, (3 reviews)
"Very clean….convenient location "
United States
Paris
The price is AU$258
includes taxes & fees
9 June - 10 June
Quaint -2-bedroom house in Lancaster with cool AC breeze

The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.4 out of 10, Exceptional, (41 reviews)
"We had a great time. Good location. Would stay again. "
United States
Deborah P.
The price is AU$492
includes taxes & fees
7 June - 8 June
The Conservatory-20 min to Lanc!

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (38 reviews)
"A group of coaches loved our stay here!! It was a beautiful home, clean, cozy, spacious, great location."
United States
Alexandra M.
The price is AU$533
includes taxes & fees
8 June - 9 June
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

Getaway on Grant, heart of Downtown with parking

Getaway on Grant, heart of Downtown with parking
Chestnut Hill
9.8 out of 10, Exceptional, (49 reviews)
"Terrific accommodations within walking distance to some shops and restaurants! Will definitely stay at this location again! "
United States
Jennifer M.
The price is AU$447
includes taxes & fees
7 June - 8 June
Getaway on Grant, heart of Downtown with parking

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
West Lancaster
9.4 out of 10, Exceptional, (40 reviews)
"Parking was no problem, in driveway or near in the street. "
United States
Maria
The price is AU$489
includes taxes & fees
10 June - 11 June
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

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

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Elizabethtown
10.0 out of 10, Exceptional, (41 reviews)
"As advertised, was perfect for our stay. "
United States
Jason M.
The price is AU$512
includes taxes & fees
10 June - 11 June
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

Enola Trail Getaway *bikes*rural

Enola Trail Getaway *bikes*rural
Pequea
10.0 out of 10, Exceptional, (6 reviews)
"I had a great time and the place was very beautiful and peaceful "
United States
Brittany R.
The price is AU$623
includes taxes & fees
8 June - 9 June
Enola Trail Getaway *bikes*rural

Lovely Downtown Townhome

Lovely Downtown Townhome
Ross
8.8 out of 10, Excellent, (118 reviews)
"Amazing host and stay! My family and I had a wonderful time here visiting Lancaster. My daughter forgot her stuffed animal and the host helped and returned it to her. Thank you!"
United States
Patrick S.
The price is AU$294
includes taxes & fees
16 June - 17 June
Lovely Downtown Townhome

Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents

Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents
East Side
10.0 out of 10, Exceptional, (29 reviews)
"Great bachelorette stay with a small group of ladies!"
United States
Tiffany N.
The price is AU$693
includes taxes & fees
10 June - 11 June
Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents

Beautiful Boho Villa on Vine in the heart of Lancaster

Beautiful Boho Villa on Vine in the heart of Lancaster
Historic Downtown Lancaster
9.4 out of 10, Exceptional, (53 reviews)
"Had a very comfortable stay. The house is beautifully renovated! "
United States
susan t.
The price is AU$503
includes taxes & fees
10 June - 11 June
Beautiful Boho Villa on Vine in the heart of Lancaster

Historic Stone House on Beaver Creek

Historic Stone House on Beaver Creek
New Providence
10.0 out of 10, Exceptional, (55 reviews)
"House was beautiful...we had everything we needed for our over night stay. "
United States
Jamie F.
The price is AU$566
includes taxes & fees
10 June - 11 June
Historic Stone House on Beaver Creek

The Garden House

The Garden House
Chestnut Hill
10.0 out of 10, Exceptional, (13 reviews)
"Cute and cozy home, all the right amenities stocked, easy in easy out, communicative host, excellent location! All the things we needed."
United States
Eleanor L.
The price is AU$463
includes taxes & fees
8 June - 9 June
The Garden House

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

Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
East Side
9.8 out of 10, Exceptional, (57 reviews)
"The amenities, the clear communication, and the accommodations are always superb! We love spending time here!"
United States
Laura H.
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
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$219 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 Dallastown Lions Club Community 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.