Holiday rentals with a pool in Cumberland County

The Wright Retreat

This is your opportunity to stay at a very special property which is minutes from the delights of Hershey, the history of Gettysburg, the Harrisburg nightlife and farmshow complex, Lancaster, or the summer or winter fun of Roundtop Resort. This home can be rented as a whole, partial, or shared space. Although excellent for entertaining, THE PRICING SHOWN IS FOR OVERNIGHT ACCOMMODATIONS ONLY. Larger groups and gatherings must be pre-approved and stated when booking. All guests must be registered.

Quaint Family Home-pet friendly

Quaint military owned family home. Great for entertaining with a bar downstairs, covered outdoor seating area, fire pit, and multiple beds. Close to the Susquehanna River for the summer days and Ski Round Top during winter time. Commute times: Hershey >20 mins Downtown Harrisburg >15 mins Lancaster >45 mins Close and easy access to main highways like 81, 83 and route 322/22. Pets are welcome with a small fee. Fenced in back yard & short walk to the green belt make this home super pet friendly!

The Mallard

Escape to the Mallard Cabin at Back Roads Camping & RV Resort in Landisburg, PA! This new log cabin features a Queen bedroom, loft with 2 Double beds, Queen sleeper sofa, full bath, AC/heat, smart TV, kitchen with full fridge, microwave, cooktop and coffee pot, and gas grill . Enjoy hand-carved decoy duck décor, a front porch swing with views of the pond and mountains. Resort offers an in-ground pool, hiking/golf cart trails, and golf cart rentals. A perfect blend of comfort and rustic charm!

The Old House 4Bed/3Bath (Whole House)

The Old House is a Bed and Breakfast in Historic Downtown Mechanicsburg that offers room and event rentals as well as the option of having the whole house to yourself! *Please note as required by zoning the host keeps a residence on a separate part of the property and will be on site during your stay, but not in the home. **Other parties may use the pool during your rental but will not have access to the house ***Price does not include price for events that include non-overnight guests.

Songbird Hollow

*Pool CLOSED until May 2026* Looking for a place to spend quality time with your family? Check out Songbird Hollow! Nestled at the foot of the Blue Mountains, this charming home offers lots of fun with a swimming pool, sandbox, swing and plenty of room to ride bikes and more! We invite you to come out and enjoy the birds while relaxing in the clean quiet country atmosphere. Located 2 hours or less from Carlisle, Hershey, Philadelphia, Gettysburg, Baltimore, DC and other local attracti

Blue Mountain Retreat

Coming to events in Carlisle or the Pennsylvania Farm Show Complex and Expo Center in Harrisburg? Come stay at the Blue Mountain Retreat, the perfect place for the whole family (max 6). Twenty minutes to the Harrisburg Farm Show Complex and Expo Center, and 20 minutes to Carlisle or Hershey. Take a day trip to Lancaster, Gettysburg, Carlisle, or Hershey and come back to relax by the pool (mid May to mid Sept) or fire pit. State Game Lands and the Appalachian are 10 minutes away.

PP 514 City Chic in a Modern Studio Haven

Unwind in style at this fully furnished studio apartment, perfectly nestled in the heart of downtown. Enjoy the convenience of a high-rise building with amazing amenities like: Sparkling pool & fitness center: Relax by the pool or get your workout in. In-unit laundry: Keep your clothes fresh and convenient. Concierge service: Get help with anything you need. Clubhouse & lounge: Relax and unwind in shared spaces. Breakfast/coffee delivery: Start your day right with delicious options.

POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!

Hershey, Gettysburg, and the Dutch Country are at your fingertips, yet you'll enter your own private retreat in this comfortable home on a large corner lot with mature trees in a peaceful neighborhood. Newly remodeled kitchen! Conveniently located to all the attractions of Central PA, with Hershey 30 minutes to the east, Gettysburg 30 minutes west, and the Amish Country 45 minutes South. Ski Roundtop is only 9 miles from the house! Easy access to PA Interstates and the PA Turnpike!

Fly Fishing Lodge at Allenberry Resort

The former Dixon Mansion now known as "The Fly Lodge at Allenberry Resort" is a unique mansion retreat nestled in the woods along the famed Yellow Breaches Creek w/ direct creek access for fishing and hiking. The property is adjacent to the famed Allenberry Resort and Barn Restaurant. The late 1800's stone mansion boasts 6 bedrooms, 2.5 bathrooms, a fully stocked whiskey lounge and library, pool table, large living room and country style kitchen w/ the original hearth fireplace.

Grove Retreat - Prime Spot,Pool,Deck,Pond,Firepit

Rural Retreat with Suburban Proximity! Relaxing Grove Retreat – Pool, Deck, Pond, Fire Pit, Playground, Large Private Yard, Wildlife. Comfortable 1,400 sq ft home that sits on 29+ private acres. PA Farm Show Complex – 12 min., 7 miles Harrisburg – 22 min., 8.3 miles Carlisle Fairgrounds – 28 min., 18.4 miles Hershey – 33 min., 22.2 miles Ski Round Top – 34 min., 21.9 miles Gettysburg – 54 min., 43.1 miles Lancaster – 57 min., 47.1 miles Linens - Included

Molly Pitcher Milk House

Bring the whole family for fun at the farm! Have family meals in the dining room, game night in the sun room, or watch a movie on the big screen TV. Take the family outside to the large patio, private pool and playground. After a fun day, relax on a comfy Purple mattress. We want to make all guests aware that this is an active, working dairy farm with cows, machinery and country air. Our farm produces renewable energy for the property and surrounding community.

Deer Run Lodge - hike, rest, relax!

Lovely cabin surrounded by Michaux State Forest with beautiful views through the large windows in the warm, spacious great room. Situated atop a mountain ridge near two state parks, with the Appalachian Trail and 40 miles of ATV trails both less than a mile away. Screened in porch, fire pit, pool, huge finished walkout basement, and large master suite. Come see why our family loves this place so much!