Holiday rentals with a pool in Pennsylvania

Mountain Getaway w/ Pool+Hot Tub

Relax with the whole family at this secluded mountain getaway. The cabin is located just a few minutes from Penn's Creek, a trout enthusiasts dream that offers endless activities like fishing, canoeing, tubing, and so much more! The cabin borders state game lands and has direct access to snowmobiling trails! The best part is that you don't even have to leave the cabin. Lounge by the pool or take in the soothing currents of the hot tub! Just 45 minutes to Penn State, 25 to Bucknell, and 35 to SU!

Mid-century A-frame nestled amongst the trees

NEW Hot tub added! This little A-frame is a mid century dream nestled among the trees in the Pocono Mountains of Northeastern Pennsylvania and is within a few minutes walk to the lake. Beautifully and loving curated, filled with mid- century furniture, lots of art, books and records. A highlight of the cabin is the upstairs bathroom, featured in Condé Nast, Houzz and West Elm, it's a Pinterest dream come true. Come take a soak in our beautiful soaker tub among the trees. 2 hours from NYC.

Rustic Private Ranch w/ Saltwater Pool & Hot Tub!

Escape the city hustle at this charming Theme Room Retreat, surrounded by nature. Enjoy three bedrooms, cozy outdoor fireplace, and a spacious open-concept living area with a fully equipped kitchen. Relax in the jacuzzi or take a dip in the private pool. The retreat offers indoor and outdoor dining, a dedicated workspace, and essential amenities like WiFi, washer/dryer, and more. Perfect for long stays, work, or leisure, this serene getaway promises a delightful experience for you and your pets.

Stunning 50s Ski Chalet, Jukebox, Hot Tub & More!

Step into our 50s diner-inspired chalet — where classic charm meets modern comfort. Highlights: *Stunning mint green fridge *Custom Diner banquette seating *A jukebox! *California king-sized bed *High-speed wifi *Dogs Welcome! *Spa-like retro-tiled bathroom *Deluxe hot-tub *Luxurious velvet sofa *Stunning spiral staircase to open loft *Adorable "Little Bear Cave" Play space *Pass-Thru Cafe Window on the deck Retro meets modern... enjoy the best of both worlds here @thehappydayschalet.

Glamping Cabin~Gazebo/ HotTub~1.5 NYC/ 1~Philly

Welcome/todos son bienvenidos~Hot tub/365 days/yr~Pool is seasonal. A romantic getaway. Comforts/amenities of a cabin with an atmosphere of camping. Experiential get-away/private gated/fenced property. Gazebo~panels, furniture,gas firepit & hot tub. Detached bathroom behind cabin.Outdoor shower, Hammock, BBQ’s, Wood firepit. Reconnect w/the outdoors.Queen bed w/firm mattress.Escape the cities to privacy. Abutted on 3 sides by a farm/pasture views.Easy to get to from points east in NYC & Philly

-The Pool Cottage at The Roundtop Estate-

Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the soothing sounds of wildlife and the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

Romantic Log Cabin W/ Hot Tub, Fire Pit, Projector

Immerse yourselves in the perfect blend of serenity and romance at our fully renovated Poconos log cabin. It offers a private feel, while located in a safe neighborhood. Cuddle up in our living room day bed while enjoying backyard forest views through the giant picture window. Relax in the hot tub or by the fire pit where memories are made! Centrally located, the cabin provides access to ski resorts and hiking trails. As guests, you'll also enjoy access to the lake, pool, and sports courts.

Cozy Pocono Cabin on an Acre

If you are looking for a quiet and intimate getaway or adventure, this is it! Step into this unique log sided cabin with all the Pocono's aesthetic you could want. Relax & recharge in the open concept knotty pine kitchen and living room. The vaulted loft provides an open & airy feel. The bedrooms feature brand new beds and large closets. The kitchen is well stocked and the living room features a wood burning fire place, Roku TV, two couches, a DVD collection, Nintendo 64 and boardgames.

Poconos Cabin Retreat w/ Hot Tub & Fireplace

Picture this: morning coffee on an oversized deck as deer wander by, evenings soaking in your private year-round hot tub under the stars, and nights curled up by the fireplace in a home guests call “exceptionally clean and incredibly cozy.” Set in a quiet private lake community and close to top Pocono attractions, Winnie’s Retreat is your peaceful reset without giving up comfort or convenience—perfect for romantic escapes, anniversaries, and unforgettable weekend getaways.

The Grey Wolf (studio-style loft suite)

Enjoy the clean, comfy, eco-friendly & private loft space with your own private HOT TUB! Situated on top of a hill in the beautiful lake area of Lititz, PA, you will enjoy lovely views and quiet privacy. The main house is detached & adjacent to the loft suite. The loft is located on the top floor of the carriage house. Explore charming downtown Lititz just 4 miles away! Pool open Memorial Day-Labor Day. Hot tub open year round. ONE parking space/EV charging fee

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Hot Tub, GameRoom, Fire Pit, Mins to Skiing, Pets

Escape to the Poconos at the Whispering Willow Lodge. Relax with family or friends at our beautifully appointed 4 bedroom + loft with plenty of space for everyone. Enjoy the outdoors on our spacious deck, have a soak in the hot tub or cozy up by the fireplace. Centrally located in Penn Estates Private, gated community which offers swimming pools, lakes, beach, tennis, volleyball & more. Minutes to skiing, water parks, shopping, rafting, hiking, and wineries.