Winterstown Holiday Rentals

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Holiday Rentals in Winterstown

2-bedroom 2nd Floor apartment in Mount Joy with off street parking

2.0 star property
Mount Joy
9.8 out of 10, Exceptional, (27)
"Loved the AC"
United States
Ben N.
The price is NZ$271
includes taxes & fees
16 Nov - 17 Nov
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Cozy Cape Cod Bungalow

3.5 star property
York
10.0 out of 10, Exceptional, (1)
"I have been looking at this property for a few years, wanting a place with a full kitchen and a private house. I gave 5 stars because it was pretty much what I was looking for. The plastic covering on the beds was a bit uncomfortable. I realize it’s more sanitary although I would suggest a washable fitted cover over the plastic mattress pad and then the sheets. It would cut the extra sweating that occurs lying on a sheet over the plastic. Also there was only one extremely worn out dish...
United States
Judith
Cozy Cape Cod Bungalow

Restful and Quaint Cottage

Conestoga
9.8 out of 10, Exceptional, (124)
"Loved the house and the fact it had everything you could need during your stay!"
United States
Kaci P.
The price is NZ$431
includes taxes & fees
19 Nov - 20 Nov
Restful and Quaint Cottage

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Yorkana
10.0 out of 10, Exceptional, (124)
"Amazing stay! Owners very polite."
United States
Amber C.
The price is NZ$751
includes taxes & fees
19 Nov - 20 Nov
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Stone Cottage at Roundtop Estate couples Retreat

Wrightsville
10.0 out of 10, Exceptional, (5)
"This property is pretty secluded and quiet. The pool and hot tub were a super plus. The pool cottage was very charming for my wife and myself. I wouldn't go with friends or children. The space is small but just right for a romantic getaway. The stringlights at dark, eating our late night snack on the patio, made for a very enchanting evening. The walking trails were nice also. We enjoyed it very much. "
United States
Ron H.
The price is NZ$684
includes taxes & fees
16 Nov - 17 Nov
Stone Cottage at Roundtop Estate couples Retreat

Cozy Farm Home Near I83. Minutes from wedding venues!

White Hall
10.0 out of 10, Exceptional, (36)
"We chose this property since it is located reasonably close to our family (grandchildren) and to the Manor Tavern and Oregon Grille our favorite restaurants in the area. Beautiful, private area in Maryland horse country!!"
United States
Donald F.
The price is NZ$483
includes taxes & fees
17 Nov - 18 Nov
Cozy Farm Home Near I83. Minutes from wedding venues!

Enola Trail Getaway *bikes*rural

Pequea
10.0 out of 10, Exceptional, (2)
"I had a great time and the place was very beautiful and peaceful "
United States
Brittany R.
The price is NZ$772
includes taxes & fees
17 Nov - 18 Nov
Enola Trail Getaway *bikes*rural

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

Airville
9.0 out of 10, Wonderful, (4)
"The gun shots were a little alarming every night."
United States
David W.
The price is NZ$748
includes taxes & fees
18 Nov - 19 Nov
The River Shack *kayaks*hottub*fishing*quiet*family

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

Willow Street
9.8 out of 10, Exceptional, (268)
"We had a wonderful stay. The place was beautifully decorated and comfortable. Very relaxing with every imaginable amenity needed. "
United States
Kevin M.
The price is NZ$499
includes taxes & fees
17 Nov - 18 Nov
River Rock Room at Muse House: Secluded Luxury in horse country.

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

Conestoga
10.0 out of 10, Exceptional, (2)
"Secluded getaway with historic history. Definitely great for those who love the outdoors. Several cool hikes nearby. "
United States
George
The price is NZ$777
includes taxes & fees
29 Nov - 30 Nov
The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature

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

Airville
10.0 out of 10, Exceptional, (5)
"The property is gorgeous and has all the necessary amenities! The host was quick to respond whenever we reached out! It was tucked away just enough but close enough to some restaurants and a winery. The only downside is the driveway is tricky, but the host gave us a tip & heads up before we arrived! Overall, it was a great spot and I’d definitely recommend it to others and come back again!"
United States
Amanda E.
The price is NZ$758
includes taxes & fees
18 Nov - 19 Nov
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

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

Columbia
9.8 out of 10, Exceptional, (9)
"We loved the house. Beautifully decorated, very clean, good mattresses... lol (it matters) loved the location."
United States
Vera
The price is NZ$701
includes taxes & fees
17 Nov - 18 Nov
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom

Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Fawn Grove
9.6 out of 10, Exceptional, (12)
"It was a quiet calm retreat for us to stay during our family time "
United States
Mary R.
The price is NZ$605
includes taxes & fees
14 Nov - 15 Nov
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Walking distance to Wellspan York Hospital, York College. Comfortably sleeps 8.

2.0 star property
York
8.8 out of 10, Excellent, (5)
"Everyone was super comfy and the hosts are quick to reply with any questions. We all loved staying."
United States
Brandy H.
The price is NZ$773
includes taxes & fees
26 Nov - 27 Nov
Walking distance to Wellspan York Hospital, York College. Comfortably sleeps 8.

Cozy Cape Cod Bungalow|King|Queen|WD|Full Kitchen|Wifi|Desk

York
7.0 out of 10, Good, (8)
"It is a very cozy home near York College, with lovely woodwork inside. Perfect local. The back & neck massagers in the dining room a very welcome surprise. Street Parking was a ease right outside the front door. We will return when visiting our York family again."
United States
Heather B.
The price is NZ$421
includes taxes & fees
14 Nov - 15 Nov
Cozy Cape Cod Bungalow|King|Queen|WD|Full Kitchen|Wifi|Desk

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Lancaster
9.8 out of 10, Exceptional, (33)
"Exceeded our expectations, would definitely rebook if we were to be in the area again"
United States
Melissa F.
The price is NZ$507
includes taxes & fees
14 Nov - 15 Nov
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

the BoatHouse waterfront

York
10.0 out of 10, Exceptional, (4)
"Great house and great location! Wished we could’ve stayed longer ! "
United States
Kelly S.
The price is NZ$766
includes taxes & fees
16 Nov - 17 Nov
the BoatHouse waterfront

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

Conestoga
8.0 out of 10, Very good, (5)
"Very beautiful property very clean. Great hosts ! Will definitely stay again"
United States
Charles
The price is NZ$844
includes taxes & fees
21 Nov - 22 Nov
Lady Grey Cottage | Hot Tub, Fireplace, King Bed, Countryside Escape

The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

3.5 star property
York
The price is NZ$559
includes taxes & fees
19 Nov - 20 Nov
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

The Quiet House on Main Street minutes from Everywhere

2.0 star property
Shrewsbury
The price is NZ$427
includes taxes & fees
22 Nov - 23 Nov
The Quiet House on Main Street minutes from Everywhere
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

Find out more about Winterstown

Everything you need to know about Winterstown 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 Winterstown 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 Winterstown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winterstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterstown. 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 Winterstown 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 Winterstown holiday rentals we have selected for you start as low as NZ$271 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winterstown rentals

At Expedia, we put the best Winterstown 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 Winterstown 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 Winterstown 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 Winterstown. 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 Winterstown?

Yes, there are holiday rentals close to the most popular sights in Winterstown, 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 Winterstown has to offer?

LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB: This holiday home rental outside of Winterstown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Winterstown?

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

What’s a holiday rental in Winterstown like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterstown. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.