Family-friendly holiday rentals in Hershey

The Sweetest Place, Hershey, Close to Everything

Welcome to Hershey! Enjoy your stay at The Sweetest Place. 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, Isaacs, Wendy’s , Pizza Hut, & Papa Johns! The Sweetest Place offers all the amenities of home, & the ideal location to spend a couple nights close to it all!

Chocolate Ave, Hershey ♥ w/ Fenced Yard

Full 2-story home on Chocolate Ave in Hershey, PA. Lots of room for the kids or friends to play in a fenced yard. Close to all things Hershey, Giant Center, pubs, restaurants, medical center, and more. Order takeout from a local restaurant, or cook a meal in the well-appointed kitchen. Relax in the rocking chairs facing East Chocolate Ave. Just minutes to Downtown Hershey, Hersheypark, etc. Also close to sports complexes in Palmyra and Lancaster. Garage parking for 2, plus 3rd off-street spot.

Tobias Cabin

This peaceful and centrally located cabin provides tranquility and relaxation in the Blue Mountains. The large wraparound porch surrounded by the lush landscape and natural beauty of the cold spring, creates an environment that you don’t want to miss. Spend your evening looking up at the stars in the hot tub or making s’mores over a fire creating lasting memories. If you choose to be adventurous there is hiking trails, biking, fishing, kayaking and several state parks with lakes nearby. Enjoy!

Whimsy in the Woods: 4 acres, pond, kids playhouse

Want a stay that's private and relaxing, but that is also an experience of its own? Whimsy in the Woods is the place. Filled w/hand-painted furniture & whimsical art, our property has something for everyone! Mins from Annville & 20 to Hersheypark, you're surrounded by woods but w/the convenience of a cute town mins away (Annville). Our four private acres feature a hot tub; pond/relaxing water fall feature; spacious screened porch, deer(!), fire pit; arcade; and lots of artistic motivation.

The Sweet Shack w/ 4bd/2ba, close to Hersheypark

Welcome to The Sweet Shack- a newly renovated home located in Hershey PA. No details were spared in this professionally decorated home that includes 4 bedrooms (2 located on the first floor), 2 bathrooms, a laundry room, fully stocked kitchen, and an amazing outdoor space including a huge deck and private fenced yard with grill and outside games for the family, and off-street parking for 6 cars. Come enjoy a pleasant and relaxing stay after an exciting day enjoying all Hershey has to offer.

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!

Hershey is minutes away! Horseshoe apartment

A perfect location to stay! You will be minutes from Hershey and a short drive to Harrisburg, Lancaster and Lititz. Located on route 322 makes it fast and easy to get around. You are in walking distance to laundromat, Brass Rail beverage and restaurant, Sopranos Pizza and Restaurant, Rising Sun restaurant and Bar, Annie's ice cream, A & M pizza, and post office. Grocery store , Chinese restaurant, nail salon, subway subs, and Bank are a short drive around the corner.

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.

Get Hersheypark Happy and unwind with our Cottage

Come unwind and get your "Hersheypark Happy" with our relaxing Cottage on the Corner. - Walking distance to Funck's (56 beers on tap) and several other Palmyra restaurants. - 8 minutes to Hersheypark, Giant Center & downtown Hershey. - 20 minutes to Mt Gretna - 30 minutes to HIA & downtown Harrisburg - 45 minutes to Lancaster - 60 minutes to Gettysburg Safe neighborhood set in an idealistic historical cottage.

The Red Barn Retreat

Welcome to The Red Barn Retreat! We are so excited for you to come visit our peaceful place. The barn was built in the early 1800’s and we completed its renovation in 2014 and an upgrade in 2020 to include air conditioning in the whole barn and new reclining leather couches. It is very special to our family and we hope it will be for you as well! It is a wonderful spot to relax and refresh and make lasting memories.

10 Mins To Hershey w/ Gameroom & Firepit

Trust In The Reviews! Our 3 Bedroom, 2 Bathroom Nest Features Modern Amenities with a Fun Retro Vibe and Private Grass Yard! Roast Marshmallows & Grill Fireside Only 10 Minutes To Hershey! The Spacious Lower Level Rec Room Features A Foosball Table, Full-Size Air Hockey Table, Big Screen TV w/ Atari Legacy Game Console, and Loads of Board Games and Books. Complimentary Netflix, Hulu and Disney +, and ESPN+!

Farm Stay! Minutes to Hershey!

Enjoy this 2023 38 foot Keystone Springdale RV surrounded by horse pastures on 26 acres. Enjoy an up close view of horses grazing in the pastures from anywhere in the RV as there are large windows and a sliding glass door. You will also meet our farm dog, horses and goats. We are just minutes to Hershey Park, Zoo America, Hershey Gardens, and the Giant Center. It’s a fabulous place for your next getaway!