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Vacation rentals in South Middleton Township

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Top-rated vacation rentals in South Middleton Township

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

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Townhouse in Carlisle

4.83 out of 5 average rating, 240 reviews

Blue Retreat in Carlisle

Welcome to Carlisle! Enjoy your stay at The Blue Retreat. Just a few short blocks for a 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 Blue Retreat offers all the amenities of home, and ideal location to spend a couple nights close to it all! Within Walking distance to a Park.

Mar 24 – 31

G$30,839 GYD per night

Cottage in Dillsburg

4.88 out of 5 average rating, 303 reviews

Private Cottage on Horse Farm with covered porch

Now using UV technology to clean which uses extra time to sanitize and ventilate see new check in/out. Lovely cottage enjoy amazing sunsets from the back porch with first floor eat in kitchen- full refrigerator, microwave, stove, coffee bar and grill. The living room features a comfy sofa and chair for reading with queen sofa bed and tv, 1st floor full bath walk in shower. 2nd floor has a lofted ceiling with a queen bed, vanity, tv, desk and chair. Lockbox entry. Pets allowed - extra fee.

Mar 10 – 17

G$26,761 GYD per night

Cottage in Dillsburg

4.95 out of 5 average rating, 174 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)

Mar 10 – 17

G$25,115 GYD per night

Apartment in Dillsburg

4.96 out of 5 average rating, 131 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.

Dec 31 – Jan 7

G$18,976 GYD per night

Apartment in Carlisle

4.93 out of 5 average rating, 218 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.

Mar 27 – Apr 3

G$20,314 GYD per night

Townhouse in Carlisle

4.9 out of 5 average rating, 169 reviews

Wilson House: 2 Blocks to Dickinson! A+ Location!

Location, location, location! Conveniently located in Southwest Carlisle, just 2 blocks from Dickinson School of Law and a short walk to Dickinson campus & Downtown Carlisle. Within walking distance to restaurants, bars, library, and shopping. This private home has amenities you've come to enjoy while away from home including wifi, a dedicated workspace, & smart tv. Enjoy a fresh cup of Keurig coffee in the cozy courtyard patio. The Wilson House - your home away from home!

May 12 – 17

G$26,892 GYD per night

Guesthouse in Carlisle

4.98 out of 5 average rating, 201 reviews

"The Carriage House"

This quaint 1,500 square feet carriage house is on the back of a property that is home to a 19th century Victorian know as "Glass Gable". In 2000 Walt and Diana Brown purchased this property and began restoration and remodeling. The woodwork and other accommodations throughout have all been carefully selected to provide the atmosphere of an European Chalet. The Carriage House is within walking distance to downtown Carlisle and its many historic attractions.

Aug 25 – Sep 1

G$30,721 GYD per night

Townhouse in Carlisle

4.96 out of 5 average rating, 228 reviews

Downtown Charmer

Located in the heart of downtown Carlisle, this home was built in the early 1900's and still holds aspects of it's historical charm. It is in close proximity to all that Carlisle has to offer such as local shopping and restaurants, Dickinson College and Penn State Law School, Army War College and Army Heritage Center, Carlisle Events car shows, and more. We do our best to provide all the comforts of home in order to make your stay as pleasant as possible!

Oct 10 – 17

G$21,812 GYD per night

Guest suite in Carlisle

4.97 out of 5 average rating, 797 reviews

Pup Friendly Private Space with fenced yard

Welcome, I am Debbie a busy Mama/Grandma with a bunch of millennial children (plus five grandchildren and 5 granddogs). I am excited to be able to offer my newly designed space close to Dickinson, the War College, Carlisle Fairgrounds, Appalachian Trail, Harrisburg and Gettysburg. You have your own off-street parking, private entrance and a large bedroom/sitting room with full private bathroom and a microwave/ mini-refrigerator for your convenience.

Oct 19 – 26

G$14,007 GYD per night

Barn in Mechanicsburg

4.97 out of 5 average rating, 203 reviews

Farm Escape at Deputy Farms

Reconnect with nature at this unforgettable escape. Come join us on our new farmette, 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. Enjoy your stay in our barn, where the first floor has been made into a 2 bedroom place where you can enjoy the peaceful outdoors . Stroll our flower gardens in season as well as apple trees.

Nov 16 – 23

G$27,018 GYD per night

Home in Boiling Springs

4.93 out of 5 average rating, 171 reviews

Single Family in Boiling Springs

Enclosed 4 person hot tub. Bluetooth speakers in hot tub area. Accordion doors that open onto a patio. Patio has fire feature. 2 bedrooms with en-suite bathrooms. One has a rain head shower and body jets, the other has a tub/shower combo. Both have comfortable queen size beds. Open concept living area includes a large flat screen smart tv, electric fireplace and full kitchen. A large dining table, and large kitchen island.

Jan 22 – 29

G$43,114 GYD per night

Tiny home in Wellsville

4.97 out of 5 average rating, 600 reviews

Cutest Tiny Home Getaway w/kayaks next to lake

Perched on an outcrop overlooking the Conewago mountains, this sweet tiny home for 2 offers a stylish, relaxing getaway where you can slow down for a few days with your favorite human. Cozy up on the hammock with a good book, spend the day on the lake with our two complimentary kayaks, roast marshmallows over the fire, sip wine to a spectacle of fireflies, settle into rocking chairs for some stargazing, and wake up happy 😊

Oct 15 – 22

G$31,008 GYD per night

Vacation rentals for every style

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Popular amenities for South Middleton Township vacation rentals

Free parking on premises

Air conditioning

Stay near South Middleton Township's top sights

Momma Spriggs Restaurant3 locals recommend

R/C Carlisle Commons Movies 84 locals recommend

Letort Park3 locals recommend

Twirly Top3 locals recommend

Allenberry Resort5 locals recommend

Caffe 1014 locals recommend

Other great vacation rentals in South Middleton Township

Cabin in New Oxford

4.9 out of 5 average rating, 599 reviews

Conewago Cabin - Near Gettysburg!

Nov 1 – 8

G$14,248 GYD per night

Guesthouse in Boiling Springs

4.97 out of 5 average rating, 73 reviews

Cozy Farmhouse Cottage

Jul 29 – Aug 5

G$19,124 GYD per night

Apartment in Mount Holly Springs

4.79 out of 5 average rating, 53 reviews

Angler's Den

Aug 24 – 31

G$22,617 GYD per night

Guest suite in Carlisle

5.0 out of 5 average rating, 17 reviews

Quiet, Spacious, Remodeled Suite Longterm Discount

Feb 7 – 14

G$19,794 GYD per night

Home in Carlisle

4.87 out of 5 average rating, 61 reviews

Modern 2-Bedroom Home with Courtyard

Nov 11 – 18

G$26,615 GYD per night

Home in Carlisle

4.92 out of 5 average rating, 25 reviews

Carlisle Luxury Townhouse

May 20 – 27

G$28,555 GYD per night

Home in Carlisle

4.98 out of 5 average rating, 43 reviews

Civil War Era Row House with Modern Amenities

Sep 19 – 26

G$28,432 GYD per night

Guesthouse in York Springs

4.94 out of 5 average rating, 35 reviews

Pondtown Mill Bridge

Oct 14 – 21

G$20,261 GYD per night

Destinations to explore