
Holiday houses in South Middleton
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Top-rated holiday rentals in South Middleton
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Golf course home with patio, sauna and fenced area
Private house on the Range End golf course w/ sauna and fenced pet area along with amazing sunsets. Right off RT15 in Dillsburg w/access to restaurants and nature. Close to Gettysburg battlefields and visitors center. Easy access to turnpike, Hershey, Lancaster, York and Carlisle. Minutes to Yellow breeches best trout stream in PA Messiah/Dickinson College close w/easy access to Carlisle for car show -garage available for extra fee. Sauna available for extra fee. Pets welcome for fee
4.79 out of 5 average rating, 107 reviews
Farm Escape at Deputy Farms
Luxury 2 bedroom apartment in the renovated lower level of a barn. Reconnect with nature at this peaceful,unforgettable escape. Our farmette is nestled away in beautiful countryside, plenty of mountains, with creeks for fishing less than 1 mile away. The famous Appalachian trail entrance is about 1.5 miles away. Stroll our cut flower gardens ( in season) and beautiful property grounds with unparalleled views. Our desire is for folks to unwind, rest, restore, and rediscover the beauty of nature.
4.98 out of 5 average rating, 482 reviews
Lovely 2BR apt between Hershey, Gettysburg
This in-law apartment is connected to the host's home, but with private entrance, and has everything you need to feel at home away from home. Beautiful quiet country setting but only 5 miles from turnpike and other major routes, as well as grocery stores, gas stations, restaurants and shopping. Midway between Gettysburg, Hershey, Harrisburg & Lancaster Amish country . Near Ski Roundtop, Messiah College, Naval Depot. Sightings of turkeys, deer and more in the back yard are not unusual.
4.97 out of 5 average rating, 184 reviews
Downtown Retreat - whole house full of amenities
Welcome to The Downtown Retreat! Just a few short blocks from the campus of Dickinson College and a quick stroll to historic downtown Carlisle restaurants and shopping. Visit one of the many car shows at Carlisle Fairgrounds, or tour the Army Heritage Center. A short drive to historic Gettysburg, the orchards of Adams County, and the capital city Harrisburg, and more! The Downtown Retreat offers all the amenities of home, and the ideal location to spend a couple nights close to it all!
4.93 out of 5 average rating, 388 reviews
POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!
Hershey, Gettysburg, and the Dutch Country are at your fingertips, yet you'll enter your own private retreat in this comfortable home on a large corner lot with mature trees in a peaceful neighborhood. Newly remodeled kitchen! Conveniently located to all the attractions of Central PA, with Hershey 30 minutes to the east, Gettysburg 30 minutes west, and the Amish Country 45 minutes South. Ski Roundtop is only 9 miles from the house! Easy access to PA Interstates and the PA Turnpike!
4.89 out of 5 average rating, 102 reviews
Cute Carlisle Cottage-studio home
Welcome to the Carlisle Cottage. Small, cute & clean. 1 Q bed & addtl. Q air bed avx upon request. Sleeps 2 adults & up to 2 children. Centrally located to shops, restaurants, US Army War College, Dickinson College, Keystone Aquatics & Fairgrounds but not walkable to these locations. Easy I81 on/off access. Minutes to the PA Turnpike. Smoking not allowed indoors but ok on the porch. Receptacle provided. Outdoor cameras for security. Host lives on property in house next door.
4.98 out of 5 average rating, 203 reviews
Cozy Farmhouse Cottage
This cottage was once the washhouse for the adjoining 1790's farmhouse and has been recently renovated into a cozy retreat, overlooking the quiet fields and rolling mountains of Boiling Springs. The queen bed in the loft and double bed in the back room offers flexibility for a quick getaway or long-term stays. Head to the private deck for a meal and view of the sunset in the evening. Carlisle is just up the road and Harrisburg is only a 25-minute drive. Come and be refreshed.
4.95 out of 5 average rating, 174 reviews
Creekview Cottage
Escape to a charming WATERFRONT cottage 🐟🦆 hardwood floors, lots of windows with views for days! Tons of wildlife, geese, ducks, cozy fire pit, pond, and direct creek access! Enjoy swimming, fishing, and relaxing on the large deck. Sleeping: comfortable queen bed (private room) and full daybed in sunroom( no door) Book your stay and create lasting memories! 20 steps to access. Nearby: Messiah Univ. , Dickinson College, Farm Show Complex, Carlisle Fairgrounds, Hershey Park
4.85 out of 5 average rating, 119 reviews
Historic Home in Downtown Carlisle - Free Parking!
Enjoy this 2 bedroom historic home in Downtown Carlisle, PA. This home is recently renovated, has free on street parking, and is within walking distance to downtown Carlisle. This rental is located UP a flight of steep steps! This rental is a townhouse, there are neighbors on both sides and below! This space is IN TOWN, please expect to hear the noises associated with living in town. Please do not book if you are not used to townhouse, in town, noise level! Space is SMALL.
4.93 out of 5 average rating, 460 reviews
The Teal Door
The whole group will enjoy easy access to everything from this centrally located place. Just five minutes from the Carlisle Fairgrounds, one block from a park with disc golf, playground, and a walking path alongside a peaceful creek. The historic district of Carlisle is only a fifteen minute drive. Large bedroom comfortably sleeps four with two queen beds. Kitchen includes refrigerator, microwave, toaster and coffee maker. Includes a private entrance and parking.
4.95 out of 5 average rating, 136 reviews
Modern 2-Bedroom Home with Courtyard
Enjoy the luxuries of home in this fully renovated downtown retreat. Within close proximity of popular downtown Carlisle restaurants, bars, Carlisle Fairgrounds, pickleball courts, and Dickinson College, this 2 BR, 1 bath home with ample street parking is the ideal location to stay a few nights or longer. This Modern Parkside Retreat is close enough to town for convenience, but sits right next to Letort Park, giving you just enough peace and quiet.
4.91 out of 5 average rating, 125 reviews
A charming cottage Victorian-style house.
Conveniently situated in walking distance to the Army War College, to gate number 1 of the Fairgrounds, and downtown restaurants and shops. This 2nd floor cozy apartment is part of a charming Victorian-style house built, in 1870. There is a eat-in kitchen with full-size appliances, the 2 bedrooms share a private bathroom and the comfortable living room provides a great place for relaxing. Apartment comes with off-street parking for 2 cars.
4.91 out of 5 average rating, 191 reviewsPopular amenities for South Middleton holiday rentals
Other great holiday rentals in South Middleton

Mountainside Hideaway - Hot Tub - Secluded
5.0 out of 5 average rating, 98 reviews
Yellow Breeches Creekfront | Kayaks & Fishing
5.0 out of 5 average rating, 60 reviews
Walkable Carlisle Getaway 3BR College & Downtown
4.98 out of 5 average rating, 47 reviews
Holly Mansion Carriage House
4.97 out of 5 average rating, 32 reviews
Spacious Family Home (Sleeps 10)
5.0 out of 5 average rating, 19 reviews
Edge of Town
5.0 out of 5 average rating, 96 reviews
Historic Carlisle Queen Anne
4.86 out of 5 average rating, 69 reviews
Hershey Park, Gettysburg, Carlisle, & Ski Roundtop
4.98 out of 5 average rating, 52 reviewsDestinations to explore
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- Hersheypark
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- Hershey's Chocolate World
- Spooky Nook Sports
- Roundtop Mountain Resort
- Cowans Gap State Park
- Cunningham Falls State Park
- South Mountain State Park
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- Franklin & Marshall College
- Pennsylvania Farm Show Complex & Expo Center
- Greenbrier State Park
- Hersheypark Stadium
- Giant Center
- Lancaster County Convention Center
- Broad Street Market
- Middle Creek Wildlife Management Area
- National Civil War Museum
- Messiah University
- Lititz Springs Park
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