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Holiday rentals in North Middleton

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Top-rated holiday rentals in North Middleton

Guests agree: these stays are highly rated for location, cleanliness and more.

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A light-filled living area showcases a comfortable sofa adorned with decorative pillows and a stylish coffee table. In the background, a dining space is visible with a table set for four, complemented by modern chairs and artwork on the walls. A potted plant adds a touch of greenery.
Home in Carlisle

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!

4.84 out of 5 average rating, 379 reviews
Top guest favourite
A single-story house is surrounded by lush green grass and a well-maintained landscape. A variety of trees and shrubs can be seen, along with a fenced yard in the background. Bright blue skies and scattered clouds create a serene setting.
Home in Shermans Dale

Country retreat, dogs ok, 15 min 81/76, Carlisle

Make yourself at home at the Country Retreat! Close to many area attractions for visitors & highways for through travelers. Plus, a huge fenced in yard & fire pit! Arriving late? The house is fully equipped with all kitchen necessities, Keurig coffee maker, microwave, coffee, tea, snacks, frozen pizzas, & canned soups. Out all day? Return & enjoy dinner under the covered pergola & a drink by the fire. Enjoy some yard games available in the shed. No cleaning/pet fee. $35/person/night over 2.

4.97 out of 5 average rating, 274 reviews
Top guest favourite
Home in Carlisle

Matt’s dream

Unwind at this peaceful quiet little home 2 miles from historical downtown Carlisle. Beautiful view of the mountains and you can watch deer in the back yard. Come for the stay, stay for the view. Sleeps up to 5, 2 bedrooms, 1 queen size bed and 1 full size bed also full size pull out sofa bed in living room and 1 bathroom. Newly remodeled kitchen, patio has grill, griddle and smoker. North Middleton park is near by as well as Opossum Lake and the fair grounds is 2.5 miles away.

4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Carlisle

Walkable Carlisle Getaway 3BR College & Downtown

Charming 1890s house directly across from Dickinson Science Center—the closest AirBNB to campus. Three bedrooms, 1.5 baths, chic farmhouse style, full kitchen, walkable to Dickinson College, Law School, Army War College, and downtown Carlisle. Quick drive to Carlisle car shows. Cozy, stylish, and perfectly located for campus visits or exploring town. Free street parking, smart lock entry. Historic charm meets unbeatable convenience. We can’t wait to host you in this beautiful space!

4.98 out of 5 average rating, 44 reviews
Guest favourite
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

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, 101 reviews
Top guest favourite
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.
Flat in Carlisle

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, 456 reviews
Top guest favourite
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.
Flat in Carlisle

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, 133 reviews
Guest favourite
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

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, 124 reviews
Top guest favourite
The exterior of a Victorian-style house built in 1870 features a wraparound porch with decorative supports. The house presents red shutters and a mix of light gray and blue siding. Two benches are positioned on the porch, surrounded by greenery, creating an inviting entryway.
Flat in Carlisle

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, 190 reviews
Top guest favourite
A spacious wooden deck is surrounded by lush greenery, featuring a cozy seating arrangement. Stone steps lead to a tidy garden area with seasonal plants and a raised stone terrace, enhancing the inviting outdoor space of the studio apartment.
Flat in Carlisle

Quiet, Cozy, Contemporary

Tucked away behind the main road, this “Fairgrounds Flat” studio apartment is centrally located in historic Carlisle Borough. Sparkling clean, contemporary stying, and filled with amenities, you will feel you are at a home-away-from-home. Enjoy a quiet evening on the beautifully arbored deck. An easy ten minute walk will bring you to the heart of downtown where everything is at your fingertips.

4.95 out of 5 average rating, 442 reviews
Top guest favourite
Cabin in Newport

A-Frame W/ HOTTub, MountainView,Pickleball/tennis

Welcome to Hilltop Haven A-Frame. Perched on top of the ridge and surrounded by trees, this unique getaway offers breathtaking views, total privacy, and a true connection to nature. Designed for both relaxation and recreation, this home has something for everyone—whether you’re unwinding in the hot tub, gathering around the fireplace, or enjoying a friendly competition outdoors.

4.98 out of 5 average rating, 360 reviews
Top guest favourite
A charming cottage is set against a backdrop of greenery, featuring a stone-accented facade and a steeply pitched roof. A clear pathway leads to the front entrance, and large windows invite natural light into the space.
Cottage in Carlisle

The Cottage Overlooking the Conodoguinet

Beautiful cottage with a large deck, a fire pit, and grill, views of the Conodoguinet Creek and amazing sunsets! Located on a private road, just 3 miles from downtown Carlisle. You will enjoy the privacy, scenic beauty and tranquility that this cottage offers. A grocery store, the Carlisle Fairgrounds and Dickinson College are located within 3 miles.

4.98 out of 5 average rating, 59 reviews

Popular amenities for North Middleton holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near North Middleton's top sights

Molly Pitcher Brewing Company

19 locals recommend

Dickinson College

17 locals recommend

US Army Heritage & Education Center

14 locals recommend

Carlisle Events

10 locals recommend

Carlisle Theatre

9 locals recommend

Letort Park

7 locals recommend

Other great holiday rentals in North Middleton

Guest favourite
The exterior of the home is shown, featuring a smooth brick and vinyl façade. A welcoming front door is positioned beneath a small porch light. Lush green grass and flowering shrubs provide a natural landscape, complemented by a neatly manicured garden bed.
Home in Carlisle

Quiet Comfort Near the Fairgrounds

4.96 out of 5 average rating, 28 reviews
Top guest favourite
The exterior of a historic Victorian home features ornate architectural details, including a welcoming front porch with seating. A decorative door adorned with seasonal decor leads into the entryway. Surrounding greenery and brickwork add to the home's charming character.
Home in Carlisle

Historic Carlisle Queen Anne

4.85 out of 5 average rating, 68 reviews
Top guest favourite
A comfortable sun room features a green sofa with decorative pillows and two wooden chairs. A wooden table is positioned between the chairs, set with a wine bottle and glasses. Large windows with blinds offer views of an outdoor patio and garden.
Flat in Carlisle

Spacious Carlisle apartment, quiet rural setting

4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Carlisle

The Fairground Retreat

5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Carlisle

Charming Cabin With Epic Views and Accessibility

4.94 out of 5 average rating, 17 reviews
Top guest favourite
Townhouse in Mechanicsburg

Spacious Family Home (Sleeps 10)

5.0 out of 5 average rating, 17 reviews
Top guest favourite
An aerial view of the house is captured, showcasing a spacious property nestled among trees. The well-maintained lawn surrounds the home, which features a gray roof and white exterior. Fields of crops can be seen in the background, contributing to the serene countryside atmosphere.
Home in Gardners

Mountainside Hideaway - Hot Tub - Secluded

5.0 out of 5 average rating, 97 reviews
Top guest favourite
A spacious living area features a warm-toned leather sofa and a light grey armchair. A round coffee table sits in the center, surrounded by wooden accents. Large windows with sheer curtains allow natural light to fill the room, creating a bright atmosphere.
Home in Carlisle

Charming 2BR Near Fairgrounds and War College!

4.97 out of 5 average rating, 92 reviews

Destinations to explore