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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation 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, (152 reviews)
"We had a great time at the Shoe House! It was a fun and unique experience!"
United States
Janelle C.
The price is ￥31,412
￥75,481 total
includes taxes & fees
Oct 6 - Oct 7
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A cabin with a deck, surrounded by trees and a small stream.

2. The Roundtop Chalet romantic couple’s getaway

The Roundtop Chalet romantic couple’s getaway
Wrightsville
9.8 out of 10, Exceptional, (15 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 ￥56,053
￥85,074 total
includes taxes & fees
Nov 5 - Nov 6
The Roundtop Chalet romantic couple’s getaway
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

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, (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 ￥15,684
￥49,715 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
A swimming pool with a covered patio area, a two-story house, and a small shed.

4. 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 ￥17,048
￥44,427 total
includes taxes & fees
Oct 6 - Oct 7
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
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)
"Wonderful stay! Cute, clean, and well stacked. Great communication with host!!"
United States
Shannon S.
The price is ￥21,625
￥84,678 total
includes taxes & fees
Oct 14 - Oct 15
Lancaster County Townhome Near Amish Country
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

6. 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 ￥23,520
￥61,473 total
includes taxes & fees
Oct 26 - Oct 27
Work & Play! Home 1 Mi to Dtwn & Central Market
A living room with a television, a sofa, a chair, and a patterned rug.

7. 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 ￥22,791
￥72,576 total
includes taxes & fees
Nov 2 - Nov 3
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A covered porch with wicker furniture, a table, and a ceiling fan.

8. 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 price is ￥32,377
￥66,196 total
includes taxes & fees
Oct 14 - Oct 15
THE RIVERFRONT BOATHOUSE
An outdoor patio area with string lights, seating, and planters.

9. 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 ￥62,832
￥76,604 total
includes taxes & fees
Oct 6 - Oct 7
Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

10. 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, (44 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 ￥20,287
￥63,330 total
includes taxes & fees
Oct 13 - Oct 14
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
A staircase with a handrail and a door at the bottom.

11. 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, (43 reviews)
"Great space, much more spacious than the photos appear!"
United States
Angela B.
The price is ￥14,522
￥24,722 total
includes taxes & fees
Oct 6 - Oct 7
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
A hallway with wooden floors, a floral rug, a chair, a radiator, and a door with blinds.

12. 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 ￥23,678
￥56,486 total
includes taxes & fees
Nov 2 - Nov 3
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

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

Work & Play! Home 1 Mi to Dtwn & Central Market
York
7.8 out of 10, Good, (6 reviews)
"The house was clean and very well stocked. Check in/check out process is simple. The owner/manager responded quickly when I had a question. Do not hesitate to book this property."
United States
Christopher A.
The price is ￥17,206
￥61,885 total
includes taxes & fees
Oct 26 - Oct 27
Work & Play! Home 1 Mi to Dtwn & Central Market
A two-story house with a balcony, a front door, and a small porch area.

14. 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, (13 reviews)
"Owner was excellent"
United States
Clint R.
The price is ￥31,965
￥50,640 total
includes taxes & fees
Oct 12 - Oct 13
The Quiet House on Main Street minutes from Everywhere
A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

15. 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 ￥35,005
￥78,720 total
includes taxes & fees
Oct 7 - Oct 8
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

16. 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, (66 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
The price is ￥19,731
￥38,676 total
includes taxes & fees
Oct 20 - Oct 21
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
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, (7 reviews)
"Great place to stay for our family!"
United States
Joseph F.
The price is ￥35,516
￥55,752 total
includes taxes & fees
Oct 6 - Oct 7
4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
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.

18. The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.6 out of 10, Exceptional, (46 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 ￥17,730
￥59,991 total
includes taxes & fees
Nov 3 - Nov 4
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.

19. 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, (304 reviews)
"The property was amazing! The host was outstanding in helping us and communicating. I would highly recommend this property as a great escape and a very peaceful place to stay."
United States
Chad C.
The price is ￥35,358
￥44,602 total
includes taxes & fees
Oct 6 - Oct 7
River Rock Room at Muse House: Secluded Luxury in horse country.
A covered deck with a grill and picnic table, a red door, and a view of trees.

20. Enola Trail Getaway *bikes*rural

Enola Trail Getaway *bikes*rural
Pequea
10.0 out of 10, Exceptional, (6 reviews)
"This was a wonderful stay, huge yard, beautiful. Calm and quiet had everything we needed for 3 families "
United States
Ryan B.
The price is ￥26,353
￥73,163 total
includes taxes & fees
Oct 6 - Oct 7
Enola Trail Getaway *bikes*rural
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

Heritage Hotel Lancaster

Heritage Hotel Lancaster

10/10 Excellent
"Great place A+"
dawn 1-night trip
Posted 5 hours ago
Heritage Hotel Lancaster

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:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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 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 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.