Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

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Superhost
A living room is depicted with a light-colored sofa and an armchair, complemented by a wooden coffee table. Two large windows are framed by floor-length navy curtains, allowing natural light to brighten the space. Art prints are displayed on the walls.
Apartment in Middletown
4.82 out of 5 average rating, 11 reviews

Two Bedroom Apt. with laundry

Cozy, newly renovated , fully furnished, 2nd and 3rd floor 2 bedroom 1 bathroom apartment. This comfortable cozy apartment is designed to be your home away from home. It is conveniently equipped with a washer and dryer on the main floor. Fully furnished kitchen for all your cooking needs. There is a comfortable living room with a smart TV. (Bus stop is a few houses down the road) This is located in a residential neighborhood. There are several stores and restaurants within a few minutes drive.

Guest favourite
The cottage exterior is illuminated by soft string lights, creating a welcoming entry. A white door with an oval window leads inside, flanked by two large windows. Two adirondack chairs are positioned nearby, with potted plants adding natural touches to the entrance.
Guesthouse in Goldsboro
4.95 out of 5 average rating, 105 reviews

Garden Cottage Charm for 2 - Near Hbg/York/Hershey

This beautifully styled cottage is truly a sanctuary - perfect for those who enjoy travel, personal retreat, or working remotely. Located on a pleasant 1.5 acre setting only 10 mins from Harrisburg and 20 mins to Messiah College, York, and Hersheypark. You will enjoy complete privacy with plenty of space to relax and make memories. A cozy living room, full kitchen, lovely bedroom with garden view (seasonal), and bath. Central AC, fresh linens, free WiFi, and parking provided. Pet/smoke-free.

Top Guest favourite
A cozy sleeping area features a spacious bed adorned with varying patterned bedding. A side table holds a small lamp, while a comfortable chair is positioned beside a dining table for two. Warm lighting enhances the inviting atmosphere, complemented by a scenic artwork on the wall.
Guest suite in Red Lion
5 out of 5 average rating, 162 reviews

Private suite with kitchenette

Private suite with kitchenette, full bath, private entrance, and free on-street parking in beautiful rural area. Quiet neighborhood. Centrally located: 30 min. to Harrisburg or Lancaster; 1 hr. to Baltimore or BWI airport; 2 hours to Philadelphia. Ski Roundtop is only 30 minutes away! Hiking and biking on local rail trail. Happy to provide recommendations for restaurants and things to do in the area. Enjoy the Keurig coffee maker, microwave, and mini-fridge; snacks and bottled water provided.

Top Guest favourite
The exterior of a spacious house is visible, featuring a stone façade and a large garage. A well-maintained yard includes colorful flowering bushes and green grass, with a concrete walkway leading to the front entrance. Window details highlight the welcoming atmosphere.
Guest suite in Harrisburg
4.89 out of 5 average rating, 596 reviews

Hill View Home

This is a spacious downstairs apartment in a beautiful newer house in a quiet neighborhood. The apartment has private entrance and a yard. There are two bedrooms. If your party has more than two people, or if you need two separate beds, there is an additional $20 charge for the second bedroom per night. The house is located close to I-81 and highway 322 less than 10 minutes drive from the state capitol and the beautiful Susquehanna river and 25 minutes from Harrisburg International Airport.

Superhost
A spacious living area features a plush green sofa and a decorative coffee table. Elegant chandeliers hang from the ceiling, and a large mirror with gold detailing is mounted above a marble fireplace. A Christmas tree is present, adding a festive touch to the room.
Apartment in Middletown
4.81 out of 5 average rating, 74 reviews

George Washington Tavern House

Welcome to a slice of history in our charming Middletown apartment! Built in 1750, this residence boasts large rounded doors, a magnificent marble fireplace with a golded mirror, and dueling chandeliers suspended from ornate plaster medallions. Immerse yourself in the past as you learn that George Washington was entertained in this very house during his visit to Middletown in October 1774. Experience the allure of a bygone era with modern comforts in our unique and historic Airbnb retreat.

Superhost
A spacious bedroom is presented, featuring a large bed with a textured white coverlet. Natural light filters in through a large window adorned with bright yellow curtains. A cozy chair is positioned beside the bed, and a staircase leads to another area of the apartment.
Apartment in Downtown Harrisburg
4.88 out of 5 average rating, 490 reviews

Sky-view Suite @ Walnut Place

Entire apartment in the heart of Downtown Harrisburg central business district. The unit overlooks capitol park. Access to a shared private courtyard. Neighboring buildings include Strawberry Square/Hilton, Gamut Theatre, Harrisburg University, Temple University PA Chamber of Business, Rachel Carson building. **Strictly non-smoking inside the building. A $500 fee will be applied for any violations.** Detailed parking information can be found in the photos.

Top Guest favourite
A stylish tiny home is nestled in a scenic environment, featuring a wooden deck and a seating area. The exterior combines white siding with wood accents, and large windows provide ample natural light. A parasol offers shade over the outdoor dining space.
Tiny home in Wellsville
4.97 out of 5 average rating, 747 reviews

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 😊

Top Guest favourite
The guesthouse features a charming exterior with a combination of brick and siding. A covered porch is highlighted by rocking chairs, surrounded by landscaped gardens and stone pathways. Lush greenery and a white fence create a serene countryside setting in the background.
Guesthouse in Middletown
4.98 out of 5 average rating, 137 reviews

Historic 1 bedroom guesthouse with parking.

Beautiful 1840's pre-Civil War country summer kitchen guesthouse situated on a private farm. Completely remodeled from floor to ceiling! Private off road parking. Within 15 minutes of all Hershey attractions and medical center. Conveniently located 3 miles from Harrisburg International Airport and short travel to various other destinations such as Spooky Nook Sports, Elizabethtown, Harrisburg, Hershey and Lancaster areas.

Guest favourite
A modern living space features a neutral gray sofa adorned with a white throw blanket and dark pillows. A large potted plant is positioned beside the sofa, and warm-toned curtains frame the window, allowing soft light to filter in.
Apartment in Middletown
4.92 out of 5 average rating, 85 reviews

Circle 12B Cozy Modern & Secluded Covered Parking

Circle 12B Airbnb is situated in a quiet cul-de-sac central to Harrisburg, Lancaster, Hershey and York. The space features one bath and one bedroom with a king-sized bed, a cozy living space including a dedicated work area and a kitchenette. Guests enjoy a private rear entrance and covered parking. The unit is 5 minutes from a Target and 20 minutes from Hershey stadium/park. Fire-stick apps require your own logins.

Guest favourite
An aerial view showcases a single-story building surrounded by lush greenery. The property features a private parking lot with several marked spaces. A path leads to the entrance, with power lines discreetly placed along the edge of the well-maintained grounds.
Apartment in Harrisburg
4.87 out of 5 average rating, 75 reviews

Ike Suite

Cozy Efficiency Near Key Attractions & Amenities Cozy efficiency just minutes from the PA Turnpike Harrisburg East exchange, Hershey Attractions, The State Capitol, Hollywood Casino, Harrisburg International Airport and Penn State Middletown campus. Ample private parking area. Driving distance to all amenities including many great restaurants, grocery stores, WalMart and Sams Club.

Guest favourite
A light-filled living area features a blue sofa, a multi-colored armchair, and a coffee table. A television is positioned on a small shelf, and two windows provide natural light. A doorway leads into the bedroom, enhancing the space's openness.
Apartment in Hershey
4.83 out of 5 average rating, 212 reviews

Parkview #5

Cozy brand new 1 bedroom apartment in historic building on 2nd floor overlooking Hersheypark. We offer contactless check in/out and room service available according to restaurant hours if you do not want to dine in person. Fenicci’s is located on the 1st floor of the building. Reminder: this is a historic building and does contain steep staircases.

Top Guest favourite
An open living area features a maroon leather sofa and matching armchair, complemented by a wooden dining table with metal chairs. Natural light fills the space, highlighting the hardwood floors and artwork on the walls. A floor lamp adds ambient illumination.
Home in Hummelstown
4.94 out of 5 average rating, 417 reviews

Hummelstown/Hershey Area Family Home

Welcome to a spacious home set up to provide you a comfortable and convenient stay in the Hershey area. This home is located in Hummelstown 4 miles from Hershey Park, close to Hershey Medical Center 2.1 miles, Harrisburg Airport 5 miles and the Farm Show Complex 8.7miles. It is perfect for families, couples and business travelers.

Popular amenities for Middletown holiday rentals

Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 20 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 390 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Middletown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests—averaging 4.8 out of 5!