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Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

1. 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 €256
includes taxes & fees
26 Oct - 27 Oct
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

2. 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 €215
includes taxes & fees
8 Nov - 9 Nov
Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk

3. 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 €432
includes taxes & fees
16 Nov - 17 Nov
Lancaster County Townhome Near Amish Country

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, (44 reviews)
"Great space, much more spacious than the photos appear!"
United States
Angela B.
The price is €141
includes taxes & fees
26 Oct - 27 Oct
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

5. 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 €400
includes taxes & fees
27 Oct - 28 Oct
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!

6. 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 €277
includes taxes & fees
26 Oct - 27 Oct
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

7. 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, (69 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
The price is €210
includes taxes & fees
26 Oct - 27 Oct
1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly

8. 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.
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

9. The Pop Loft | Downtown Lancaster

The Pop Loft | Downtown Lancaster
West End
The price is €233
includes taxes & fees
26 Oct - 27 Oct
The Pop Loft | Downtown Lancaster

10. "City Hideaway: Off-Grid Luxe"

"City Hideaway: Off-Grid Luxe"
Cabbage Hill
10.0 out of 10, Exceptional, (24 reviews)
"Really cute and well done tiny home. We really enjoyed our stay."
United States
Kyle M.
The price is €197
includes taxes & fees
22 Nov - 23 Nov
"City Hideaway: Off-Grid Luxe"

11. 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 €309
includes taxes & fees
26 Oct - 27 Oct
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

12. 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 €364
includes taxes & fees
27 Oct - 28 Oct
Stone Cottage at Roundtop Estate couples Retreat with hot tub

13. Getaway on Grant, heart of Downtown with parking

Getaway on Grant, heart of Downtown with parking
Chestnut Hill
9.8 out of 10, Exceptional, (51 reviews)
"Terrific accommodations within walking distance to some shops and restaurants! Will definitely stay at this location again! "
United States
Jennifer M.
Getaway on Grant, heart of Downtown with parking

14. 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 €327
includes taxes & fees
26 Oct - 27 Oct
Beautiful Boho Villa on Vine in the heart of Lancaster

15. The River Shack *kayaks*hottub*fishing*quiet*family

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.8 out of 10, Exceptional, (13 reviews)
"This property was great, everything you could need was provided. We really enjoyed our stay"
United States
Barb R.
The price is €392
includes taxes & fees
26 Oct - 27 Oct
The River Shack *kayaks*hottub*fishing*quiet*family

16. Comfy renovated townhome - heart of Downtown Lancaster

Comfy renovated townhome - heart of Downtown Lancaster
Chestnut Hill
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay, plenty to do in the neighborhood and walkable to downtown."
United States
Ted S.
The price is €301
includes taxes & fees
9 Nov - 10 Nov
Comfy renovated townhome - heart of Downtown Lancaster

17. 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, (16 reviews)
"Owner was excellent"
United States
Clint R.
The price is €294
includes taxes & fees
26 Oct - 27 Oct
The Quiet House on Main Street minutes from Everywhere

18. Quaint 2 BDRM With Fenced in Backyard

Quaint 2 BDRM With Fenced in Backyard
Chestnut Hill
9.4 out of 10, Exceptional, (6 reviews)
"Easy access to downtown Lancaster."
United States
Debbie
The price is €354
includes taxes & fees
9 Nov - 10 Nov
Quaint 2 BDRM With Fenced in Backyard

19. The Churchtowne Hideaway | Downtown | Central

The Churchtowne Hideaway | Downtown | Central
Churchtowne
8.0 out of 10, Very good, (8 reviews)
"Beautiful, spotless apartment in a great location! Easy walk to the Central Market and so many great eating spots. "
United States
Theresa B.
The price is €178
includes taxes & fees
28 Oct - 29 Oct
The Churchtowne Hideaway | Downtown | Central

20. 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 €354
includes taxes & fees
2 Nov - 3 Nov
The Conservatory-20 min to Lanc!
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, apart-hotels, 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 favorite 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 depends 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 €141 per night. Entering your travel dates in the search wizard you might find 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.