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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Windsor holiday rentals

A unique, modern building with a curved facade, a central entrance with a staircase, and a small porch area.

1. Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!

Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
Yorkana
10.0 out of 10, Exceptional, (150 reviews)
"Fun house to stay in. Despite uniqueness of home, it has everything you need for a comfortable stay. We enjoyed the hot tub in the evening and a couple trip to York for good food."
United States
Abigail H.
The price is AU$576
includes taxes & fees
8 Sept - 9 Sept
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

2. 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, (43 reviews)
"Everything was clean and as described. Great location, and easy check in/out."
United States
Joseph S.
The price is AU$413
includes taxes & fees
8 Sept - 9 Sept
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
A modern kitchen with white cabinets, a dining area with a round table and chairs, and a living room with a brown sofa and cushions.

3. Close to Wellspan, York College, Appell! Washer/dryer in unit.

Close to Wellspan, York College, Appell! Washer/dryer in unit.
York
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay "
United States
Eugene-Marinel B.
The price is AU$395
includes taxes & fees
18 Sept - 19 Sept
Close to Wellspan, York College, Appell! Washer/dryer in unit.
A staircase with a handrail and a door at the bottom.

4. 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, (40 reviews)
"The property was clean the communication with the owner was very clear for parking and how to access the property, and everything was in working order."
United States
Craig
The price is AU$206
includes taxes & fees
8 Sept - 9 Sept
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

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

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Mountville
10.0 out of 10, Exceptional, (42 reviews)
"Great house in a great location"
United States
Kate H.
The price is AU$546
includes taxes & fees
8 Sept - 9 Sept
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
A living room with a television, a sofa, a chair, and a patterned rug.

6. The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
3.5 star property
York
The price is AU$653
includes taxes & fees
21 Sept - 22 Sept
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A swimming pool with a covered patio area, a two-story house, and a small shed.

7. 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, (41 reviews)
"Property was very clean very homey"
United States
Anna
The price is AU$387
includes taxes & fees
6 Sept - 7 Sept
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
A fireplace with a fire, a television mounted above it, and a potted plant to the right.

8. The Conestoga Cottage | Hot Tub, Rustic Charm, Near Downtown Lancaster

The Conestoga Cottage | Hot Tub, Rustic Charm, Near Downtown Lancaster
Conestoga
9.8 out of 10, Exceptional, (20 reviews)
"It was very clean and very fun staying there"
United States
Henry g.
The price is AU$513
includes taxes & fees
10 Sept - 11 Sept
The Conestoga Cottage | Hot Tub, Rustic Charm, Near Downtown Lancaster
A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

9. 1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
Lancaster
10.0 out of 10, Exceptional, (62 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
The price is AU$327
includes taxes & fees
8 Sept - 9 Sept
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
A modern interior with a sofa, rug, wooden accents, and a view through a door.

10. "City Hideaway: Off-Grid Luxe"

"City Hideaway: Off-Grid Luxe"
Cabbage Hill
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful and cozy tiny house, helpful and accommodating host. "
United States
Sarah B.
The price is AU$250
includes taxes & fees
7 Sept - 8 Sept
"City Hideaway: Off-Grid Luxe"
A living room with a teal sofa, a brown ottoman, and a wooden coffee table. There is a dining area with a table and chairs.

11. The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.6 out of 10, Exceptional, (45 reviews)
"The house was as advertised. Very clean and easy check in process. Close and easy drive to Spooky Nook Sports."
United States
Julie L.
The price is AU$503
includes taxes & fees
8 Sept - 9 Sept
The Conservatory-20 min to Lanc!
A kitchen with a black backsplash, white countertops, a black faucet, and a window with greenery above the sink.

12. The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature

The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature
Conestoga
10.0 out of 10, Exceptional, (4 reviews)
"Secluded getaway with historic history. Definitely great for those who love the outdoors. Several cool hikes nearby. "
United States
George
The price is AU$457
includes taxes & fees
27 Sept - 28 Sept
The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature
A glass-top table with chairs, a potted plant, and a tray with glasses and plates on a deck with a white sofa and wooden railing.

13. Modern Farmhouse Getaway I 2 BR, Sleeps 6

Modern Farmhouse Getaway I 2 BR, Sleeps 6
Elizabethtown
10.0 out of 10, Exceptional, (86 reviews)
"Was awesome, quiet, clean, kitchen stocked, beds very comfortable. "
United States
Sharon W.
The price is AU$398
includes taxes & fees
7 Sept - 8 Sept
Modern Farmhouse Getaway I 2 BR, Sleeps 6
A modern kitchen with granite countertops, white cabinetry, and a built-in seating area.

14. The Loft at Riverside

The Loft at Riverside
Lancaster
9.4 out of 10, Exceptional, (61 reviews)
"We stayed for 2 nights and all the amenities were wonderful - clean, comfortable, and gave us easy access to all the sites in Lancaster."
United States
Deborah R.
The price is AU$296
includes taxes & fees
13 Sept - 14 Sept
The Loft at Riverside
A hallway with wooden floors, a floral rug, a chair, a radiator, and a door with blinds.

15. Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
York
4.6 out of 10, (8 reviews)
"The house itself has beautiful antique features, particularly the wooden entryway. Despite the unusual cold snap, the radiators kept us very warm."
United States
Stephen N.
The price is AU$505
includes taxes & fees
6 Sept - 7 Sept
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A two-story wooden deck with a staircase leading to a covered patio area.

16. Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country

Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country
Columbia
10.0 out of 10, Exceptional, (12 reviews)
"Great hosts! Super cute rental with everything we needed and even more than we expected. The property is beautiful and felt like an oasis! We will be back! Thankful for a peaceful place to stay and a great ride with the horses! "
United States
Sarah M.
The price is AU$390
includes taxes & fees
22 Sept - 23 Sept
Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country
A living room with a sectional sofa, a flat-screen TV mounted on the wall, a ceiling fan, and a large window with curtains.

17. Luxury Stay in Elizabethtown

Luxury Stay in Elizabethtown
Elizabethtown
10.0 out of 10, Exceptional, (14 reviews)
"Everything worked and the place was exactly as advertised. Would definitely stay there again"
United States
Daniel M.
The price is AU$514
includes taxes & fees
8 Sept - 9 Sept
Luxury Stay in Elizabethtown
A modern kitchen with dark cabinetry, stainless steel appliances, and pendant lighting.

18. Modern Downtown Lancaster Apt – Walk to Train & Amtrak

Modern Downtown Lancaster Apt – Walk to Train & Amtrak
Ross
8.6 out of 10, Excellent, (10 reviews)
"Nicely remodeled place."
United States
Didier S.
The price is AU$313
includes taxes & fees
7 Sept - 8 Sept
Modern Downtown Lancaster Apt – Walk to Train & Amtrak
A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

19. Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom

Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
Columbia
9.6 out of 10, Exceptional, (15 reviews)
"We loved staying here. Perfect for what our family needed."
United States
Debbie E.
The price is AU$596
includes taxes & fees
8 Sept - 9 Sept
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
A modern kitchen with white cabinets, stainless steel appliances, a dining area with two chairs, and a trash bin.

20. 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, (48 reviews)
"The property was perfect for us. It had everything we needed, was comfortable, clean and spacious. We will definitely be back."
United States
Robert T.
The price is AU$485
includes taxes & fees
7 Sept - 8 Sept
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
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

Eden Resort and Suites, BW Premier Collection

Eden Resort and Suites, BW Premier Collection

10/10 Excellent
"Love, love love to staying here again 💕"
ruso 2-night trip
Posted 16 hours ago
Eden Resort and Suites, BW Premier Collection

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$245 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?

Quaint -2-bedroom house in Lancaster with cool AC breeze: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Haines Shoe House 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.