Holiday rentals with a pool in Cumberland County

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Popular amenities for Cumberland County rentals with a pool

House rentals with a pool

Top guest favourite
Home in Mechanicsburg
5 out of 5 average rating, 23 reviews

Pool, Hot Tub, Ski Roundtop, Hershey Park.

LeslieRating, 5 stars2 months ago
We had an excellent stay. It snowed and the owner was extremely responsive and had the driveway shoveled and iced for us within 45 minutes. The house is beautiful and we can’t wait to come back in the summer to take advantage of the amazing backyard pool.
Home in Mechanicsburg
4.88 out of 5 average rating, 8 reviews

The Wright Retreat

AndréaRating, 5 stars8 months ago
Michael was a great host and excellent communicator. He was able to help us out when our trip was in jeopardy of falling apart. The space is huge and very unique. The location is amazing !
Guest favourite
Home in Newville
4.95 out of 5 average rating, 39 reviews

Songbird Hollow

BasemRating, 5 stars1 week ago
Charity was a great host and the place is very peaceful and perfect to have a retreat, beautiful nature and nearby trails and not to far of a drive to the nearby towns. Highly recommended!
Guest favourite
Home in Mechanicsburg
5 out of 5 average rating, 8 reviews

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

TonyaRating, 5 stars6 months ago
We had a great stay at the historic home in Mechanicsburg. Great location- awesome home.
Home in Enola
4.6 out of 5 average rating, 15 reviews

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

SherriRating, 5 stars2 months ago
This is our second stay in this house. When we are in the area we will continue to stay here. Cindy is great to work with. She is quick to respond and takes care of things quickly as well. We experienced a snow/ice storm while there and Ralph came out to pretreat the deck, stairs and walkway for our safety.
Guest favourite
Home in Shippensburg
4.96 out of 5 average rating, 27 reviews

Molly Pitcher Milk House

RalphRating, 5 stars6 months ago
Beautiful home, very comfortable, very tranquil
Guest favourite
Home in Mechanicsburg
4.88 out of 5 average rating, 77 reviews

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

AmandaRating, 5 stars2 weeks ago
We really enjoyed this place. It was a great location and only 30 minutes from Hershey (which we also visited while there). The house was in a location that felt safe and clean. My daughter and I went for a walk on the sidewalk our first evening there. The back yard is fenced in and when out there you felt as though you were in our own secluded oasis. The house is older and quirky (that we all enjoyed), but has this comfortable charm about it. Our group enjoyed the air hockey table and the pool (even though it was 54 degrees and cloudy) that didn’t keep them from the pool. Brooks reach out before our arrival with check in information and was very friendly and helpful. We enjoyed our stay and looking forward to staying again when we visit the area.
Home in Boiling Springs
4.7 out of 5 average rating, 33 reviews

*Private Pool* at The Olde Family Fishing Lodge

StephenRating, 5 stars5 months ago
my kids and I traveled here from NC to visit my parents who have recently moved to an assisted living facility in Carlisle. It was a beautiful setting and great to fish the yellow breeches again, which I fished often as a kid growing up in PA. In the morning we looked out the second story window and saw a bald eagle perched on a branch over hanging the creek, eating a fish. We would definitely stay here again.

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