Vacation rentals with a pool in Cumberland County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cumberland County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Home in Mechanicsburg

4.88 out of 5 average rating, 8 reviews

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.

Guest favorite

Home in Newville

4.94 out of 5 average rating, 35 reviews

Songbird Hollow

*Pool is CLOSED for the season* 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 attractions.

Guest favorite

Home in Mechanicsburg

5 out of 5 average rating, 16 reviews

Pool, Hot Tub, Ski Roundtop, Hershey Park.

Enjoy the privacy of this beautiful 5 bedroom and 3.5 bath home with space for 14 to sleep comfortably. Conveniently located 30 minutes from Hershey Park, 14 minutes to Round top ski resort, and a 1/2 mile to the Yellow Breeches Creek. Plenty of room to spread out and enjoy all this home has to offer. Stunningly beautiful backyard with pool, hot tub, large patio with firepit, 18x40 covered deck with an outdoor kitchen. Not to mention stunning sunsets. Inside you will find a gourmet kitchen.

Guest favorite

Home in Mechanicsburg

5 out of 5 average rating, 8 reviews

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.

Guest favorite

Farm stay in Mechanicsburg

4.95 out of 5 average rating, 20 reviews

Rustic historic farmhouse charm

Enjoy the natural beauty surrounding this historic getaway. This 250 year old log farmhouse, retains much of its old world charm, with exposed logs, vintage bathtub, wood burning log stove, plus all the modern conveniences that make it a comfortable and memorable stay, at a working farm. The perfect stay for families and bridal parties attending weddings at one of the nearby venues, for family getaways who want to gather around the fire pit, or spend a hot summer day in the in-ground pool.

Guest favorite

Home in Mechanicsburg

4.88 out of 5 average rating, 72 reviews

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!

Home in Enola

4.57 out of 5 average rating, 14 reviews

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

Guest favorite

Home in Shippensburg

4.96 out of 5 average rating, 27 reviews

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.

Guest favorite

Tiny home in Landisburg

5 out of 5 average rating, 10 reviews

The Cabana Cabin

Escape to the country in a cozy cabin with fantastic mountain views, private entrance & parking. Situated just over Blue Mountian from Carlisle, this cabin offers the best of the area year-round! Enjoy hiking, fishing, swimming, the Carlisle auto expo, Dickinson College, Shippensburg, Hershey Park, & more! Enjoy a week, weekend, or a night of simple relaxation. This rustic cabin is located in Free Spirit Campground in Landisburg, PA!

Guest favorite

Home in Marysville

5 out of 5 average rating, 38 reviews

Blue Mountain Retreat

Ready to get away? Come stay at the Blue Mountain Retreat, the perfect place for the whole family (max 6). Thirty minutes from Hershey Park, 20 minutes to Harrisburg City Island and Farm Show Complex. Take a day trip to Lancaster, Gettysburg, Carlisle, or Ski Round Top and come back to relax by the pool (mid May to mid Sept) or fire pit. State Game Lands and the Appalachian Trail are only 5 minutes away.

Guest favorite

Cabin in Biglerville

4.98 out of 5 average rating, 55 reviews

Deer Run Lodge-hike the forest & relax by the fire

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!

Superhost

Home in Boiling Springs

4.69 out of 5 average rating, 32 reviews

The Olde Family Fishing Lodge

Nestled beside the tranquil sounds of the Yellow Breeches creek, our charming Olde Family Fishing Lodge awaits your arrival. This picturesque retreat, steeped in history and surrounded by nature's splendor, offers a unique getaway experience. Whether you're an avid fly-fisherman, a lover of the outdoors, or simply in need of some peaceful relaxation, our lodge is the perfect destination.