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Winterstown Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winterstown vacation rentals

A two-story house with a balcony, a front door, and a small porch area.

1. 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, (12 reviews)
"Owner was excellent"
United States
Clint R.
The price is AED 774
AED 1,195 total
includes taxes & fees
7 Oct - 8 Oct
The Quiet House on Main Street minutes from Everywhere
An outdoor patio area with string lights, seating, and planters.

2. 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 AED 1,462
AED 1,783 total
includes taxes & fees
5 Oct - 6 Oct
Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
A unique, modern building with a curved facade, a central entrance with a staircase, and a small porch area.

3. 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 AED 731
AED 1,756 total
includes taxes & fees
5 Oct - 6 Oct
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

4. 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 AED 547
AED 1,430 total
includes taxes & fees
26 Oct - 27 Oct
Work & Play! Home 1 Mi to Dtwn & Central Market
A living room with a television, a sofa, a chair, and a patterned rug.

5. 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 AED 565
AED 1,727 total
includes taxes & fees
27 Oct - 28 Oct
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A cabin with a deck, surrounded by trees and a small stream.

6. 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 AED 858
AED 1,445 total
includes taxes & fees
5 Oct - 6 Oct
The Roundtop Chalet romantic couple’s getaway
A hotel room with a large bed, bedside lamps, a desk, and a chair.

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

Historic Schoolhouse Getaway with Private Hot Tub Retreat in York, Pennsylvania
York
Historic Schoolhouse Getaway with Private Hot Tub Retreat in York, Pennsylvania
A bedroom with a sliding glass door, a bed with white bedding, and a nightstand.

8. Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
Airville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful peaceful spot."
United States
Emily L.
The price is AED 1,098
AED 2,077 total
includes taxes & fees
5 Oct - 6 Oct
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
A wooden cabin with a circular entrance, a fire pit, and a stone pathway leading to it.

9. 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, (3 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 AED 621
AED 1,460 total
includes taxes & fees
5 Oct - 6 Oct
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
A kitchen with a black backsplash, white countertops, a black faucet, and a window with greenery above the sink.

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

The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature
Conestoga
9.8 out of 10, Exceptional, (6 reviews)
"Secluded getaway with historic history. Definitely great for those who love the outdoors. Several cool hikes nearby. "
United States
George
The price is AED 453
AED 1,173 total
includes taxes & fees
8 Oct - 9 Oct
The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

11. 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 AED 400
AED 1,440 total
includes taxes & fees
26 Oct - 27 Oct
Work & Play! Home 1 Mi to Dtwn & Central Market
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

12. 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 AED 313
AED 1,092 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Cozy living room with a blue sectional sofa, neutral decor, and wall art

13. 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
Lady Grey Cottage | Hot Tub, Fireplace, King Bed, Countryside Escape
A cozy outdoor patio area with wicker furniture, string lights, and a dining table set for a meal.

14. 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 AED 518
AED 1,975 total
includes taxes & fees
14 Oct - 15 Oct
Lancaster County Townhome Near Amish Country
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 AED 562
AED 1,327 total
includes taxes & fees
1 Nov - 2 Nov
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A swimming pool with a covered patio area, a two-story house, and a small shed.

16. 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 AED 397
AED 1,034 total
includes taxes & fees
5 Oct - 6 Oct
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
A wooden cabin with a fire pit in the center, surrounded by Adirondack chairs.

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

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.6 out of 10, Exceptional, (10 reviews)
"This property was great, everything you could need was provided. We really enjoyed our stay"
United States
Barb R.
The price is AED 536
AED 1,582 total
includes taxes & fees
5 Oct - 6 Oct
The River Shack *kayaks*hottub*fishing*quiet*family
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

18. 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 AED 472
AED 1,474 total
includes taxes & fees
26 Oct - 27 Oct
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
A covered porch with wicker furniture, a table, and a ceiling fan.

19. 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 AED 753
AED 1,540 total
includes taxes & fees
14 Oct - 15 Oct
THE RIVERFRONT BOATHOUSE
A dining area with a wooden table and chairs, a chandelier, and sheer curtains.

20. 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 AED 826
AED 1,297 total
includes taxes & fees
28 Oct - 29 Oct
4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
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 Winterstown Hotel Reviews

Sleep Inn & Suites of Lancaster County

Sleep Inn & Suites of Lancaster County

10/10 Excellent
"The staff was great and gave us some places to check out while we were there. Next to it was a unique ice cream place that was very cozy with all the colorful umbrellas and table. And they also served food."
Brenda 4-night trip
Posted 1 day ago
Sleep Inn & Suites of Lancaster County

Frequently asked questions

Can I find vacation rentals in Winterstown?

Yes, we have vacation rentals near top local attractions in Winterstown, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Winterstown has to offer?

River Rock Room at Muse House: Secluded Luxury in horse country. : This vacation home rental near Winterstown is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Winterstown?

Explore the area and family-friendly sights such as Shank's Mare, or get out into nature at a spot like Rocky Ridge Park. In the larger area, you’ll find Heritage Hill Golf Course and Penn State York.

What’s a vacation rental in Winterstown like?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winterstown. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.