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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Windsor vacation rentals

Exterior

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 ￥23,735
￥66,889 total
includes taxes & fees
Sep 8 - Sep 9
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
Interior

2. 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, (38 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 ￥12,208
￥22,247 total
includes taxes & fees
Aug 24 - Aug 25
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Exterior

3. 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, (42 reviews)
"Everything was clean and as described. Great location, and easy check in/out."
United States
Joseph S.
The price is ￥16,718
￥46,914 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Interior

4. 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, (19 reviews)
"It was very clean and very fun staying there"
United States
Henry g.
The price is ￥23,147
￥58,523 total
includes taxes & fees
Sep 10 - Sep 11
The Conestoga Cottage | Hot Tub, Rustic Charm, Near Downtown Lancaster
Exterior

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 ￥24,646
￥63,095 total
includes taxes & fees
Sep 8 - Sep 9
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Comfort House | Living area

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 ￥27,356
￥77,755 total
includes taxes & fees
Sep 16 - Sep 17
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
Outdoor pool

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 ￥17,235
￥44,914 total
includes taxes & fees
Aug 30 - Aug 31
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
Smart TV, fireplace, books

8. 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, (60 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
The price is ￥19,779
￥34,931 total
includes taxes & fees
Sep 20 - Sep 21
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
Interior

9. The Loft at Riverside

The Loft at Riverside
Lancaster
9.4 out of 10, Exceptional, (60 reviews)
"We had a great stay. The apartment was clean and cozy. It was exactly as described and perfect for our needs. The driveway parking was convenient and the host was very responsive. Will definitely stay again if we are in the area. "
United States
Jennifer L.
The price is ￥12,184
￥33,357 total
includes taxes & fees
Sep 13 - Sep 14
The Loft at Riverside
TV

10. 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 ￥23,439
￥61,381 total
includes taxes & fees
Sep 1 - Sep 2
The Conservatory-20 min to Lanc!
Interior

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 ￥27,767
￥62,539 total
includes taxes & fees
Sep 16 - Sep 17
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
Property grounds

12. 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, (2 reviews)
"We had a perfect weekend at this little cabin get-away! The listing pictures portrayed the site perfectly. Well before check-in, the D-Lux team was in touch to make sure we had check-in codes and to answer any questions if we would have had them. Upon arrival the place was spotless and very inviting. It was adequately stocked with necessities and even had a few extra touches that we appreciated. The hammock, hottub, and sauna were clean and perfect and helped us have a truly relaxing weekend....
United States
Megan K.
The price is ￥24,799
￥61,539 total
includes taxes & fees
Aug 24 - Aug 25
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
Coffee/tea maker, fridge, microwave, oven

13. 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 ￥21,424
￥53,236 total
includes taxes & fees
Aug 30 - Aug 31
The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature
Smart TV, fireplace, books

14. Luxury Stay in Elizabethtown

Luxury Stay in Elizabethtown
Elizabethtown
10.0 out of 10, Exceptional, (13 reviews)
"Everything worked and the place was exactly as advertised. Would definitely stay there again"
United States
Daniel M.
The price is ￥31,215
￥71,617 total
includes taxes & fees
Aug 25 - Aug 26
Luxury Stay in Elizabethtown
Smart TV, DVD player, books, video library

15. "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 ￥18,527
￥28,545 total
includes taxes & fees
Sep 1 - Sep 2
"City Hideaway: Off-Grid Luxe"
Interior

16. 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, (8 reviews)
"Very clean….convenient location "
United States
Paris
The price is ￥21,203
￥26,890 total
includes taxes & fees
Sep 2 - Sep 3
Quaint -2-bedroom house in Lancaster with cool AC breeze
Property grounds

17. THE WINTER HOUSE - HISTORIC DOWNTOWN LANCASTER

THE WINTER HOUSE - HISTORIC DOWNTOWN LANCASTER
Musser Park
8.4 out of 10, Very Good, (5 reviews)
"A great place to sleep. It had everything we needed from a coffee pot and toaster to a great shower and comfy bed. We were very comfortable there. "
United Kingdom
Sierra G.
The price is ￥21,065
￥44,660 total
includes taxes & fees
Aug 24 - Aug 25
THE WINTER HOUSE - HISTORIC DOWNTOWN LANCASTER
Exterior

18. 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 ￥19,150
￥49,856 total
includes taxes & fees
Sep 1 - Sep 2
Modern Farmhouse Getaway I 2 BR, Sleeps 6
Exterior

19. The Roundtop Chalet romantic couple’s getaway

The Roundtop Chalet romantic couple’s getaway
Wrightsville
9.8 out of 10, Exceptional, (13 reviews)
"Our stay the Roundtop Chalet was a wonderful retreat. We had stunning views of the snowfall and enjoyed delicious espresso & waffles. The recommend the comfortable bed and the hot tub. "
United States
Amy S.
The price is ￥49,901
￥77,649 total
includes taxes & fees
Aug 24 - Aug 25
The Roundtop Chalet romantic couple’s getaway
Exterior detail

20. Sunrise Balcony, private back porch centrally located minutes to 83 & Rt 30

Sunrise Balcony, private back porch centrally located minutes to 83 & Rt 30
York
6.8 out of 10, (9 reviews)
"Lots of space, very inviting and cozy space and the host was so accommodating. Thank you for the stay!"
United States
Valerie R.
The price is ￥19,937
￥38,243 total
includes taxes & fees
Aug 27 - Aug 28
Sunrise Balcony, private back porch centrally located minutes to 83 & Rt 30
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
"Everything and location"
Brandon 3-night trip
Posted 1 hour ago
Eden Resort and Suites, BW Premier Collection

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we offer vacation rentals near popular points of interest in Windsor, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental that Windsor has to offer?

Quaint -2-bedroom house in Lancaster with cool AC breeze: This vacation home rental near 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 Chickies Rock Park. Heritage Hill Golf Course and AvalancheXpress are a couple of places you'll find in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are private properties you can stay in for a long or short time in Windsor. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.