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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (154 reviews)
"We had a great time at the Shoe House! It was a fun and unique experience!"
United States
Janelle C.
The price is AU$720
includes taxes & fees
27 Oct - 28 Oct
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A spacious living area with a stone fireplace, large windows, and a cozy seating arrangement.

2. Stone Cottage at Roundtop Estate couples Retreat with hot tub

Stone Cottage at Roundtop Estate couples Retreat with hot tub
Wrightsville
10.0 out of 10, Exceptional, (10 reviews)
"A beautiful property and such a relaxing space. Everything was top notch. We hated to leave."
United States
Rebecca H.
The price is AU$588
includes taxes & fees
26 Oct - 27 Oct
Stone Cottage at Roundtop Estate couples Retreat with hot tub
An outdoor patio area with string lights, seating, and planters.

3. Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9

Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
York
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great. Enjoyed the outdoor area. Hot tub was clean. Coffee bar was well stocked with coffee. We appreciated that."
United States
Adam B.
The price is AU$724
includes taxes & fees
22 Nov - 23 Nov
Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

4. 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)
"Perfect for the six of us visiting family in the area. The kitchen amenities we needed for breakfast, comfy beds, and a clean house."
United States
Emmy Lou H.
The price is AU$455
includes taxes & fees
17 Nov - 18 Nov
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
A cozy outdoor patio area with wicker furniture, string lights, and a dining table set for a meal.

5. Lancaster County Townhome Near Amish Country

Lancaster County Townhome Near Amish Country
Columbia
10.0 out of 10, Exceptional, (4 reviews)
"Great place"
United States
David S.
The price is AU$692
includes taxes & fees
26 Oct - 27 Oct
Lancaster County Townhome Near Amish Country
A covered porch with wicker furniture, a table, and a ceiling fan.

6. THE RIVERFRONT BOATHOUSE

THE RIVERFRONT BOATHOUSE
York
10.0 out of 10, Exceptional, (11 reviews)
"The house was very clean and well appointed."
United States
Amanda M.
THE RIVERFRONT BOATHOUSE
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, (42 reviews)
"Property was very clean very homey"
United States
Anna
The price is AU$393
includes taxes & fees
25 Oct - 26 Oct
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
A two-story house with a balcony, a front door, and a small porch area.

8. The Quiet House on Main Street minutes from Everywhere

The Quiet House on Main Street minutes from Everywhere
Shrewsbury
9.8 out of 10, Exceptional, (14 reviews)
"Owner was excellent"
United States
Clint R.
The price is AU$449
includes taxes & fees
26 Oct - 27 Oct
The Quiet House on Main Street minutes from Everywhere
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

9. 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, (45 reviews)
"We had a lovely stay for our gaming weekend. The check in process was easy and we enjoyed being within walking distance of a restaurant."
United States
Melissa S.
The price is AU$575
includes taxes & fees
25 Oct - 26 Oct
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
A staircase with a handrail and a door at the bottom.

10. 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, (44 reviews)
"Great space, much more spacious than the photos appear!"
United States
Angela B.
The price is AU$230
includes taxes & fees
26 Oct - 27 Oct
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Cozy living room with a blue sectional sofa, neutral decor, and wall art

11. Lady Grey Cottage | Hot Tub, Fireplace, King Bed, Countryside Escape

Lady Grey Cottage | Hot Tub, Fireplace, King Bed, Countryside Escape
Conestoga
8.4 out of 10, Very good, (7 reviews)
"Very beautiful property very clean. Great hosts ! Will definitely stay again"
United States
Charles
The price is AU$757
includes taxes & fees
13 Nov - 14 Nov
Lady Grey Cottage | Hot Tub, Fireplace, King Bed, Countryside Escape
A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

12. 1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly

1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly
Lancaster
10.0 out of 10, Exceptional, (68 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
The price is AU$330
includes taxes & fees
26 Oct - 27 Oct
1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly
A living room with a fireplace, wooden beams, a television, and a red sofa.

13. Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk

Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk
York
7.4 out of 10, Good, (10 reviews)
"Beautiful home in a quiet, convenient location. The check in process was easy, parking available in front of the house and the home was well equipped with linens and cook ware. I was a little hesitant considering some of the other reviews complaining about the house being hot but the 2 window units provided was more than enough during a very humid summer weekend. Thank Todd for sharing your home!"
United States
Larissa D.
The price is AU$334
includes taxes & fees
8 Nov - 9 Nov
Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk
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.

14. The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.6 out of 10, Exceptional, (47 reviews)
"The property was exactly as described which is always a plus in our book. An eclectic home that was a lot of fun to explore. Well decorated but whimsically, not predictable. Where modernization was essential (kitchen and bathrooms) it was exquisite. We absolutely enjoyed our stay there and would book it again."
United States
John
The price is AU$536
includes taxes & fees
27 Oct - 28 Oct
The Conservatory-20 min to Lanc!
A spacious bedroom with a four-poster bed, a sitting area with a chair and a small table, and large windows with blinds.

15. River Rock Room at Muse House: Secluded Luxury in horse country.

River Rock Room at Muse House: Secluded Luxury in horse country.
Willow Street
9.8 out of 10, Exceptional, (307 reviews)
"Very fully equipped rental- very spacious and quiet."
United States
Greg P.
The price is AU$394
includes taxes & fees
25 Oct - 26 Oct
River Rock Room at Muse House: Secluded Luxury in horse country.
A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

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

Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
Columbia
9.8 out of 10, Exceptional, (17 reviews)
"We loved staying here. Perfect for what our family needed."
United States
Debbie E.
The price is AU$593
includes taxes & fees
3 Nov - 4 Nov
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
A dining area with a wooden table and chairs, a chandelier, and sheer curtains.

17. 4-bedroom house in amazing Lancaster County in quaint village of Conestoga.

4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
Conestoga
8.6 out of 10, Excellent, (8 reviews)
"Great place to stay for our family!"
United States
Joseph F.
The price is AU$488
includes taxes & fees
25 Oct - 26 Oct
4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
A backyard with a pergola, outdoor seating, and a hot tub.

18. Historic Schoolhouse Getaway with Private Hot Tub Retreat in York, Pennsylvania

Historic Schoolhouse Getaway with Private Hot Tub Retreat in York, Pennsylvania
York
The price is AU$840
includes taxes & fees
22 Nov - 23 Nov
Historic Schoolhouse Getaway with Private Hot Tub Retreat in York, Pennsylvania
A hallway with a wooden floor, a brick wall, and a staircase leading to another room.

19. 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, (59 reviews)
"This was a beautiful rental that was exactly as described. The communication was fantastic and the location was perfect."
United States
Lori
The price is AU$516
includes taxes & fees
9 Nov - 10 Nov
Beautiful Boho Villa on Vine in the heart of Lancaster
A wooden cabin with a circular entrance, a fire pit, and a stone pathway leading to it.

20. Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy

Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
Delta
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$646
includes taxes & fees
26 Oct - 27 Oct
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
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

8/10 Good
"Liked that had housekeeping everyday"
Michael 3-night trip
Posted 2 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$230 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 Corn Cob Acres Field of Fun, 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.