Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

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

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Guest favourite
A charming cabin is set beside a serene pond, featuring a colorful fountain that lights up the water. Soft string lights illuminate the outdoor space, creating a cozy atmosphere amidst the surrounding trees.
Cabin in Wrightsville
4.98 out of 5 average rating, 229 reviews

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

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, 125 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.

Guest favourite
The image captures a historic farmhouse surrounded by lush green lawns. Decorative trees, including one with pink blossoms, enhance the outdoor setting. A winding gravel path leads to the house, flanked by a stone border and blooming flowers, creating a serene and inviting atmosphere.
Home in Middletown
4.86 out of 5 average rating, 121 reviews

Fulling Mill Inn B& B - Lodging and dining

Newly renovated historic, elegant 1860 farmhouse. Bed and Breakfast or whole house rental. Your group can have us serve meals or you can make your own. We offer Bedrooms with en suite bathrooms with whole house amenities and 1.5 acres with lovely creek. Discounts offered for the full week or monthly rental. Located 1/4 mile from Harrisburg - Hershey Turnpike gate. Harrisburg Intl. Airport is 10 minutes away. Visit for family vacations, business travelers, or girls getaways.

Top Guest favourite
A bright living area features two large sofas and an armchair, arranged around a simple coffee table. A television is mounted above a white-brick fireplace. Natural light fills the room through large windows dressed with soft curtains, enhancing the cozy cottage atmosphere.
Home in Elizabethtown
4.98 out of 5 average rating, 134 reviews

Countryside Cottage

Come and enjoy this cozy home away from home! You will find this renovated home to have just what your family needs while being closely located to many popular attractions! We are located just minutes off of rt 283. Being very centrally located to the following: Hershey-10 min Harrisburg-20 min Lancaster-20 min We are very close to Hershey park, Spooky Nook sports, and many wedding venues in the area. With a cozy cottage feel you will find plenty of relaxation here in the country!

Top Guest favourite
A modern living area is furnished with a light-colored sectional sofa and stylish accent chairs. A round coffee table sits at the center, complemented by a textured area rug. The space features a mix of warm wood and neutral tones, with artistic wall decor enhancing the setting.
Home in Harrisburg
4.98 out of 5 average rating, 600 reviews

Modern, Fashionable Uptown Harrisburg home

Modern and fabulously decorated single family, brick row home in the "Olde Uptown" neighborhood of Harrisburg. Personal touches are found throughout with complimentary snacks and beverages, continental breakfast, incredibly comfortable beds, and professionally designed interior decor. You can walk to the fantastic Broad Street Market, local cafes and coffee, and the beautiful riverfront trail. One dedicated off-street parking spot is assigned to the home so parking is a breeze.

Top Guest favourite
The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.
Place to stay in Airville
4.98 out of 5 average rating, 261 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Top Guest favourite
A spacious open-concept living area features modern cabinetry and a large kitchen island with seating. Warm string lights illuminate the space, highlighting the comfortable seating area and expansive windows that offer natural light. Hardwood floors add a welcoming touch.
Apartment in Harrisburg
4.96 out of 5 average rating, 145 reviews

Midtown's Coolest Penthouse Apt—Free Parking!

Historic Midtown Retreat: Discover the perfect blend of history and modern comfort in our spacious 2-bedroom, 2-bath apartment, located on the top floor of an old department store. Ideal for lively gatherings or cozy escapes, this unique space in Harrisburg’s trendy Midtown offers easy access to Downtown, the State Capitol, and local breweries. Enjoy free off-street parking, a fully stocked kitchen, and in-unit laundry. Explore Hershey and Harrisburg from this unique spot!

Guest favourite
Home in Harrisburg
4.97 out of 5 average rating, 663 reviews

Walk to Midtown From Contemporary Uptown Harrisburg Home

Beautifully remodeled, single family, brick rowhome in the "Olde Uptown" neighborhood of Harrisburg. Take advantage of the extra care and personal touches in this property such as complimentary beverages and snacks, continental breakfast items, professionally designed interior, and incredibly comfortable king sized bed. You can walk to the fantastic Broad Street Market, local coffee shop and cafe, and the beautiful riverfront trail.

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
4.96 out of 5 average rating, 777 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
A comfortable living area features a spacious brown leather sofa and a vibrant orange armchair, complemented by a decorative area rug. Natural light enters through two large windows adorned with light curtains, creating a welcoming atmosphere. Shelving with decorative items adds character to the space.
Guesthouse in Middletown
4.98 out of 5 average rating, 160 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
4.94 out of 5 average rating, 111 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.

Top Guest favourite
A spacious porch area is visible, featuring a swing chair and a small table. The view displays the tranquil Conewago Creek, bordered by lush greenery and trees, creating a serene environment for relaxation.
Cabin in York Haven
4.94 out of 5 average rating, 605 reviews

Conewago Cabin #3

All are welcome in our cozy 1 Bedroom plus loft Cabin #3 along the Conewago Creek. Peaceful and relaxing, & the creek is just a step away and is great for splashing around in the summer to cool off. No smoking. Fully equipped kitchen & Washer and Dryer. Carport parking space. Pets are welcome. All pets must be disclosed prior to check in. We charge a $20 pet fee. Two pets maximum please.

Popular amenities for Middletown holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Middletown?

    Middletown has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Middletown?

    Experience the best of Middletown with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 10 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Middletown?

    Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Royalton, and over 130 vacation rentals in Middletown.

  • Do apartment rentals in Middletown have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middletown have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Middletown?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 400 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, Wifi and Pool across Middletown rentals

  • 4.8 Average rating

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