Vacation rentals in South Middleton

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Top-rated vacation rentals in South Middleton

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Top guest favorite
The entrance features a set of double black doors framed by wooden paneling, inviting guests inside. Lanterns are positioned on either side, and seasonal wreaths adorn the doors, contributing to a warm welcome. The surrounding walls showcase a rustic white barn aesthetic.
Barn in Mechanicsburg
4.98 out of 5 average rating, 477 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.

Superhost
Home in Dillsburg
4.79 out of 5 average rating, 105 reviews

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

Top guest favorite
The living area features a comfortable black leather sofa, accompanied by a cozy reading lamp and a coffee table. A large window allows natural light to illuminate the space, revealing views of colorful autumn foliage outside. A dining table is visible, set for meals.
Cottage in Dillsburg
4.96 out of 5 average rating, 371 reviews

Country Cottage by the Redwoods.

This quaint country cottage is nestled in the Redwoods on our Dillsburg property away from the hustle and bustle of a busy life. Relaxing, quiet, not visible from the road but close to: ~ Round Top Mountain Resort ~Paulus Mt Airy Orchards ~Yellow Breeches Creek ~Messiah University. (all within 3 miles) We are central to Gettysburg and Hershey (30 miles), Harrisburg,Carlisle, Boiling Springs, Allen Berry Play house, the Appalachian Trail, and LeTort Spring Run! (all within15 miles)

Top guest favorite
Place to stay in Shippensburg
5.0 out of 5 average rating, 484 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

Guest favorite
A sleek sectional sofa with green accent pillows is positioned around a round coffee table. The area features a neutral color palette and modern wall mirrors. A view into the dining area and kitchen is visible in the background, enhancing the open layout.
Home in Carlisle
4.93 out of 5 average rating, 386 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!

Top guest favorite
The charming creek-front home is set against a backdrop of tall trees, reflecting in the clear water. A spacious deck and landscaped yard are visible, providing a serene outdoor space. The house features a modern exterior with large windows, allowing for natural light.
Cottage in Boiling Springs
5.0 out of 5 average rating, 59 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.

Guest favorite
A spacious backyard features a large in-ground pool with two fountains, surrounded by a concrete deck. Lounge chairs are positioned around the pool, and vibrant flowers add color. A screened gazebo is visible in the background, providing shaded seating for relaxation.
Home in Mechanicsburg
4.89 out of 5 average rating, 101 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!

Top guest favorite
The front exterior of the Carlisle Cottage is shown, featuring a light-colored facade and a welcoming green door. A wooden porch is accessible via a set of steps, furnished with two chairs and a small table. An awning provides shade above the entrance.
Home in Carlisle
4.98 out of 5 average rating, 199 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.

Top guest favorite
The bright living area features a comfortable gray sofa and a cozy accent chair, complemented by a vintage rug. A small dining table is visible, and a staircase leads to a lofted sleeping area. Natural light streams through the windows, highlighting the warm wooden accents.
Guesthouse in Boiling Springs
4.95 out of 5 average rating, 171 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.

Guest favorite
A bedroom showcases a wooden bed frame with a patterned white bedspread, accompanied by decorative pillows. Soft lighting is provided by wall sconces on either side. A sleek plant and small bedside table add a touch of greenery, while a natural area rug complements the wooden floor.
Apartment in Carlisle
4.93 out of 5 average rating, 456 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.

Top guest favorite
A spacious bedroom features two queen beds with soft blue bedding. A cozy armchair with a floral pattern is positioned beside a wooden bench. Natural light is provided by a window, and a decorative area rug adds a colorful touch to the floor.
Apartment in Carlisle
4.95 out of 5 average rating, 132 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.

Guest favorite
The living room features a light-colored sofa accented by teal and gray throw pillows. Two armchairs in contrasting colors provide additional seating. A textured area rug anchors the space, while natural light filters in through the windows, enhancing the homey atmosphere.
Home in Carlisle
4.91 out of 5 average rating, 124 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.

Popular amenities for South Middleton vacation rentals