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, 25 reviews

Pool, Hot Tub, Ski Roundtop, Hershey Park.

JenessaRating, 5 stars1 month ago
This was truly an incredible place away from home and I feel so lucky to have found it. Every amenity was available, from coffee, teas; to toiletries, hairdryers, curling irons; to kitchen appliances and bbq’ing and pool amenities; to board games, etc. as well. The entire stay went as smooth as possible from start to finish and the host was accessible and responsive within minutes of reaching out and was beyond accommodating and gracious. This property is beautiful and well cared for, but the outdoor space was simply unmatched. The pool, hot tub, and outdoor shower was the most precious way to spend a day relaxing or unwinding after hectic days. Incredible is an understatement. This place is close enough to shopping but far away enough you feel a million miles away (in a good way). The sound of the pool water and birds chirping with a cup of coffee in the morning will be etched in my memory ❤️ You will not regret staying here, guaranteed. Thank you Chris and family ❤️
Home in Mechanicsburg
4.88 out of 5 average rating, 8 reviews

The Wright Retreat

AndréaRating, 5 stars10 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
4.93 out of 5 average rating, 43 reviews

Songbird Hollow

LoriRating, 5 stars2 weeks ago
We were in the area for a FORD car show in Carlisle and the location was great. Very peaceful. Be sure to check out the King's Bakery there nearby.
Guest favourite
Home in Mechanicsburg
5 out of 5 average rating, 9 reviews

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

SheilaRating, 5 stars1 month ago
wonderful stay, excellent host abd very interesting unique property. it was a joy to meet Dylan and he is 100 percent committed to ensuring his guests have a great experience. lots of extra touches, beautiful gardens, lovingly curated decor, great snacks, coffee, toiletries and very comfortable beds. i would highly recommend Dylan as a host
Home in Enola
4.6 out of 5 average rating, 15 reviews

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

SherriRating, 5 stars4 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, 28 reviews

Molly Pitcher Milk House

CarringtonRating, 5 stars2 weeks ago
This was our second stay at the Molly Pitcher Milk House! It was just as beautiful as last year. Amanda was very helpful and responsive. Check in was easy. The house is amazing, spacious and cozy. The pool and backyard amenities were great and enjoyable. We’d definitely stay again!
Guest favourite
Home in Mechanicsburg
4.88 out of 5 average rating, 81 reviews

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

FredericRating, 5 stars3 weeks ago
Brooks’ place proved to be perfect for a party of 11, including 4 boys aged 7-12. The interior was spotless and perfectly functional. The back yard (including the pool) was simply outstanding. Brooks himself was a terrific host whose messages were always helpful and considerate. Mechanicsburg itself is close to Gettysburg and some beautiful parks. No hesitation at all recommending this outstanding house and model host.
Home in Boiling Springs
4.65 out of 5 average rating, 40 reviews

*Private Pool* at The Olde Family Fishing Lodge

CameronRating, 5 stars4 weeks ago
Bill and Tia (manager) did a great job explaining and being responsive. The house had a lot of different rooms and options. The pool wasn't open yet but was still worth the price and time.

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