Holiday rentals 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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Top guest favourite
The exterior of a rustic retreat is displayed, featuring a two-story structure with a stone lower level and wooden upper sections. A spacious front porch is adorned with hanging plants, providing a welcoming entryway. Lush green grass surrounds the building.
Home in Elizabethtown
4.97 out of 5 average rating, 207 reviews

The Springhouse at Sunnyburn Farm

While away balmy evenings with barbecues on the deck at this rustic retreat with wooden beams, exposed stone walls, and elegant sash windows. Decompress with leisurely morning chats on the porch swing, then whip up a snack in the chic gray kitchen. This home has 3 bedrooms with en suite bathrooms in each bedroom plus a common area with a daybed and mattress underneath. Note:there are no bathtubs, just showers. Our other properties : airbnb.com/h/windmillmanoratsunnyburnfarm airbnb.com/h/1893suiteatsunnyburnfarm PET POLICY IS FIRM. Please do not ask to bring them. Thank you. Beautiful furnishings, new hvac,plumbing. Totally renovated. Guests have access to the whole house on acres of farmland. There is a large deck with a grill and front porch with a swing. There is a swing in the backyard for the children. Phone or text me at 717-572-9876. My email is cindi@crowetransportation.com. Please let me know of any issues or questions you may have. The property is located in the country on acres of farmland. Explore the middle of Amish country, near Hersheypark, Lititz, Mount Gretna, Nook Sports and many other Lancaster County tourist areas. Harrisburg International Airport -- 17 miles Rails to Trail -- 2 miles Lititz -- 18 miles Hershey and Hersheypark-11 miles Lancaster -- 20 miles Mt Gretna -- 6 miles Spooky Nook Sports Complex -- 11 miles Star Barn/Ironstone Ranch -- 7 miles Renaissance Faire - 5 miles Lebanon Valley College -- 11 miles Harvest View Barn -- 1.5 miles Weddings on Memory Lane -- 4 miles Elizabethtown College -- 7 miles PET POLICY IS FIRM. Please do not ask to bring them. Thank you. Our other listing We are in the country and even though we have wifi, it can be spotty at times. Hershey and Hersheypark-11 miles Harrisburg International Airport -- 17 miles Rails to Trail -- 2 miles Lititz -- 18 miles Lancaster -- 20 miles Mt Gretna -- 6 miles Spooky Nook Sports Complex -- 11 miles Star Barn/Ironstone Ranch -- 7 miles Renaissance Faire - 5 miles Lebanon Valley College -- 11 miles Harvest View Barn -- 1.5 miles Weddings on Memory Lane -- 4 miles Elizabethtown College -- 7 miles

Top guest favourite
A charming two-story brick cottage features a yellow front door and white window shutters. Lush green grass frames the home, while blooming pink flowers enhance the inviting exterior. Trees provide shade, and a paved path leads to the entrance, contributing to a welcoming ambiance.
Cottage in Harrisburg
4.99 out of 5 average rating, 101 reviews

A Wee Bit of Scotland near Harrisburg & Hershey

Coorie Doon is Scottish for "snuggle down", and that is exactly what we want you to do! We have created a cozy getaway that reflects our Scottish heritage, nestled in a neighborhood near Harrisburg, and just a few miles from Hershey. We encourage you to sit back and enjoy the cottage , or head out to explore all the Harrisburg/Hershey area has to offer, or a bit of both! There are great restaurants, shopping and entertainment venues nearby. The cottage is a unique space to make lasting memories.

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.
Guest house in Goldsboro
4.95 out of 5 average rating, 121 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, 128 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 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.
Flat in Midtown
4.96 out of 5 average rating, 141 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!

Top guest favourite
The charming stone house is bathed in warm light, highlighting its inviting windows. Lush landscaping features a gravel pathway and seating areas, with a fire pit surrounded by chairs. Soft lighting strung between trees creates a cozy ambiance in the outdoor space.
Cottage in Stevens
5 out of 5 average rating, 119 reviews

Cozy Cottage •HOT TUB • FIRE PIT• Peaceful Getaway

🌾 Welcome to Your Cozy Farm Retreat A peaceful, private guest cottage located on our small, quiet farm — complete with your own private hot tub, fire pit, and beautiful views. This is the perfect escape to relax, recharge, and enjoy the countryside. Sip coffee overlooking the fields, unwind in the hot tub under the stars, or explore the local farms, breweries, and trails nearby. Perfect for couples or solo travelers seeking a quiet getaway.

Top guest favourite
The living area features a mix of seating with a gray sofa and a brown leather chair, arranged around a round coffee table. A large television is positioned on a shelf unit, while soft light enters through a window adorned with sheer curtains.
Home in Midtown
4.97 out of 5 average rating, 654 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.

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.
Guest house in Middletown
4.98 out of 5 average rating, 149 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.
Flat in Middletown
4.93 out of 5 average rating, 103 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
Flat in Elizabethtown
5 out of 5 average rating, 186 reviews

The Goldfinch I Luxe Stay for 2 w/ Hot Tub

Welcome to The Goldfinch at The Nest at Deodate, a thoughtfully designed apartment offering a comfortable and private retreat. Set in a peaceful country setting just a short drive from Hershey and Elizabethtown, this inviting space is ideal for unwinding and relaxing. Enjoy your private hot tub and outdoor patio, and settle into an atmosphere designed for rest and connection.

Guest favourite
A shaded outdoor area features a wooden swing, suspended above a deck overlooking a serene creek. The gentle flow of water can be seen, framed by trees and grass along the banks, creating a peaceful setting for relaxation.
Cabin in York Haven
4.89 out of 5 average rating, 424 reviews

Conewago Cabin #2

All are welcome in our cozy Cabin #2 along the Conewago Creek. 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. Single Car Garage. Private Fire pit and charcoal grill. Pets are welcome. All pets must be disclosed prior to check in. We have 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 house rentals in Middletown have a kitchen?

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

  • Do apartment rentals in Middletown have wifi?

    Absolutely! We offer over 10 apartment 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 wifi, over 10 homes with air conditioning, 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 £22 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Middletown holiday rentals include wifi 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!