
Holiday rentals 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
ValueLocationWifi
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.
FamilyValueAccuracy
4.98 out of 5 average rating, 483 reviews
School Of Law - Whole House Full of Amenities
Enjoy your stay at The Law office 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 LawOffice Retreat offers all the amenities of home, and ideal location to spend a couple nights close to it all!
LocationValueHospitality
4.85 out of 5 average rating, 382 reviews
The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ
Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures. *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger
LocationValueBiking
5.0 out of 5 average rating, 489 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.
LocationValueDecor
4.97 out of 5 average rating, 184 reviews
Yellow Breeches Creekfront | Kayaks & Fishing
Creekfront on the Yellow Breeches. The first thing you notice is the water. This home sits on the bank of the Yellow Breeches, a renowned central-PA trout stream, with four kayaks at the water's edge, a firepit, and room for eight. Mornings move slowly: coffee on the porch, mist off the creek, a heron on the bank. Paddle or cast a line by day, then gather around the fire after dark. Minutes from Boiling Springs and Allenberry Resort. Come to fish, unplug, or bring everyone together.
ValueFamilyOutdoor spaces
5.0 out of 5 average rating, 61 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!
FamilyLocationLayout
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.
LocationValueGetting around
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.
LocationFamilyKitchen
4.95 out of 5 average rating, 174 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.
LocationValuePets
4.93 out of 5 average rating, 461 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.
ValueFamilyAir conditioning
4.95 out of 5 average rating, 139 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.
ValueFamilyCheck-in
4.91 out of 5 average rating, 125 reviewsPopular amenities for South Middleton holiday rentals
Other great holiday rentals in South Middleton

Walkable Carlisle Getaway 3BR College & Downtown
LocationFamilyComfort
4.98 out of 5 average rating, 47 reviews
Spacious Family Home (Sleeps 10)
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5.0 out of 5 average rating, 19 reviews
Edge of Town
FamilyValueCleanliness
5.0 out of 5 average rating, 96 reviews
Historic Carlisle Queen Anne
LocationFamilyPets
4.86 out of 5 average rating, 69 reviews
Peaceful Dillsburg Apartment
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5.0 out of 5 average rating, 42 reviews
Holly Mansion Carriage House
FamilyValueKitchen
4.97 out of 5 average rating, 32 reviews
Hershey Park, Gettysburg, Carlisle, & Ski Roundtop
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4.98 out of 5 average rating, 52 reviews
Castle by the creek
FamilyLocationAmenities
5.0 out of 5 average rating, 15 reviewsDestinations to explore
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- Hersheypark
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