Holiday rentals in Middletown

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

Spacious Private Family Home

Convenient private location nestled in the Allendale Community. Close to I-83/81, PA Turnpike & Rts 15. Centrally located to Hershey, Lancaster, Harrisburg, York & all spots in between! Convenience stores, quick food, pizza, frozen yogurt & Starbucks are a quick drive away. This space home hosts 4 bedrooms with a king, two queens and a twin daybed with trundle. 3.5 baths will make getting ready a breeze. Laundry room w/ washer & Dryer for your convenience. Perfect spot for your family vacation!

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.

Cozy Cape Cod

Our Cozy Cape Cod is located in a quiet neighborhood near many local attractions. Hershey Park & Entertainment is only a 15 min drive! Explore the caves at Indian Echo Caverns and learn about the areas rich history. Several Museums & natural trails are just a short drive away. Near several forms of public transportation as well. Harrisburg International Airport & Amtrak. *Please note: A picture of a valid drivers license/ photo ID may be requested to approve and confirm your booking request.

The Cottage on 80th close to Hershey

On the edge of a working Christmas tree farm overlooking the Hershey countryside, The Cottage on 80th is less than a 2-hour drive from major cities like DC, Baltimore, Philadelphia, and New York; only 30 minutes from Lancaster, and a quick 8-minute drive to Hershey – we are close to every major attraction but removed from noise and busyness. Completely remodeled, thoughtfully furnished, curated with local artists, and outfitted with everything you need to feel relaxed and rejuvenated.

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!

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.

Private Cottage for Getaway for 2

A romantic getaway, or a time for solitude, at the stunning Liberty Spring House located at Stone Gables Estate in Elizabethtown, Pennsylvania. Cultivate a tranquil state of mind by relaxing on the private veranda overlooking Lake Liberty. Queen bed, fire place, claw foot tub, and walk-in shower will provide much relaxation in addition to the plush robes for use during your stay. Close to: Hershey, Lancaster, Harrisburg

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.

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.

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.

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.