
Holiday rentals in Middletown
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Top-rated holiday rentals in Middletown
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Cocoa Retreat Duplex, Close to everything
Welcome! Enjoy your stay at Cocoa Retreat. Just a few min from Giant Center, Hershey Park & all its attractions. Close to Hershey Downtown, Restaurants, Shops & Penn State Hershey Medical Center. Visit Indian Echo Caverns in Middletown. Close to the State Capital Harrisburg. Walking distance to Aroogas, Sheetz , Taco Bell, McDonald’s , Isaacs, Wendy’s , Pizza Hut, KFC & Papa Johns! The Cocoa Retreat offers all the amenities of home, & the ideal location to spend a couple nights close to it all!

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.

Conewago Cabin #1
Here you will find a quiet, simple place to stay with a nice view overlooking the creek. It has all the necessary amenities. Fully stocked kitchen with dishwasher. Full size washer and dryer. There is a small porch overlooking the creek. Sony 50" smart tv Keurig with a complimentary assortment of coffee pods. Fireplace This cabin has its own private fire pit. *Pets are welcome, there is a once per stay $20 pet fee. Two pets maximum please. **No smoking or vaping of any kind is allowed.

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.

2BR Apt: Fenced Yard + King | Near Roundtop Ski
Remodeled private lower-level 2BR apartment with private entrance, smart-lock self check-in, off-street parking, and a large fenced yard + covered deck (great for pets). Easy access to Harrisburg + day trips to Hershey, Lancaster, and Gettysburg. Drive times: Pinchot 15m • Harrisburg/City Island 15m • Roundtop 20m • Fort Hunter/Wildwood 20m • Hersheypark 25m • Lancaster & Gettysburg 45m Amenities: Smart TV, Wi-Fi, laundry, fridge, stove, toaster oven, microwave, grill, Keurig + pods.

Newly Remodeled Midtown Apartment
Newly renovated Boho style apartment in the heart of Midtown. This cute and comfy apartment finds itself within walking distance to all Harrisburg has to offer. Including Midtown Cinema, Front Street’s walking path with a river view, City Island ball field and recreation, PA State Museum, the Capital, the new Federal Courthouse, Midtown Market, and unique places to eat, drink, and socialize. This special place is a short drive to Hershey, Gettysburg and other tourist attractions.

Entire Townhome w/ Hot Tub 5 min drive to Hershey!
1900 sq ft- Wonderful spacious relaxing home away from home. A great central location to the Hershey Area. Close to Hershey Downtown, Restaurants, Shops & Penn State Hershey Medical Center. Visit Indian Echo Caverns in Middletown. Close to the State Capital Harrisburg. Radha offers all the amenities of home, & the ideal location to spend a couple nights close to everything. Ideal for families with small children, couples, and large groups. Located in a very quiet and safe community.

Entire House: Historic Midtown - Inviting|Pristine
Quiet, cozy, clean. Entire house, in Historic Midtown. Pristine home with just the right balance of classical architecture and modern conveniences. Private backyard with kitchen garden and cafe-style seating. Walkable neighborhood with coffee shops, restaurants, craft brewery, Italian bakery, independent bookstore, farmers market and more (see section on neighborhood). Free street parking. If parking is a challenge, contact me for directions to free lot parking around the corner.

Harvest Moon 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. Very safe location. **Strictly non-smoking inside the building. A $500 fee will be applied for any violations.** Detailed parking information can be found in the photos.

The Barn on Fox Alley
Welcome to The Barn on Fox Alley—a piece of history nestled in the heart of Lancaster city. The Barn on Fox Alley is a repurposed garage built in 1999, transformed into a magnificent Amish barn that pays homage to Lancaster county’s rich heritage. Step inside, and you'll find yourself immersed in the warmth and character of a bygone era. The spacious interior of the barn is meticulously adorned with hand-hewn reused floors and reclaimed barn wood throughout.

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.

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 😊
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

Near Hershey & Harrisburg w/ Fire Pit & Game Room

Family home in the country

Ike Suite

The Farmhouse

The Jolly Rancher

5 Minutes from Hershey Park/ Hershey Giant Center!

Cozy Cape Cod

The Loft
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.
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.
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 wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Middletown?
Experience the best of Middletown with our apartment 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.
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.
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 air conditioning, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Hersheypark
- Liberty Mountain Resort
- French Creek State Park
- Roundtop Mountain Resort
- Codorus State Park
- Caledonia State Park
- Hershey's Chocolate World
- Pennsylvania Farm Show Complex & Expo Center
- Sight & Sound Theatres
- Spooky Nook Sports
- Amish Village
- Lititz Springs Park
- Messiah University
- Central Market Art Co
- Shady Maple Smorgasbord
- Fulton Theatre
- Franklin & Marshall College
- Lancaster County Convention Center
- Broad Street Market
- National Civil War Museum
- Giant Center
- Maple Grove Raceway
- Hawk Mountain Sanctuary
- Rausch Creek Off-Road Park




