Holiday rentals with a pool in Pennsylvania

4.99 out of 5 average rating, 216 reviews

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.

4.89 out of 5 average rating, 561 reviews

An inviting outdoor area is illuminated by soft string lights, creating a cozy ambiance. Comfortable seating is arranged around a small table, surrounded by well-maintained greenery. The cabin's rustic wooden exterior is visible in the background, set against a twilight sky.

Tiny home in Alburtis

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

4.98 out of 5 average rating, 122 reviews

A two-story condo is framed by a blanket of fresh snow, showcasing a warm earth-toned façade. A small set of steps leads to the entrance, flanked by snow-covered trees and a calm winter landscape, creating a serene and inviting atmosphere.

Apartment in Champion

Seven Springs *Ski-in/out Condo 1 Bed.(king),1 Bth

Nestle into this cozy, one bedroom condo in The Villages at Seven Springs Mountain Resort. This retreat boasts easy ski-in/ski-out access to the slopes via the Villages Trail behind the condo building (weather permitting). What makes this condo special is the private entrance, large living space, a bedroom with king bed, a full kitchen, and a balcony. As a guest, you have access to the free shuttle service or visit the clubhouse with pool, hot-tub, basketball and tennis in the summer months.

A spacious common area is highlighted by a green pool table positioned in the foreground. The wood paneled walls and vaulted ceiling create an inviting atmosphere. Soft lighting is provided by decorative lamps, and a cozy seating arrangement offers comfort for relaxation or socializing.

4.92 out of 5 average rating, 102 reviews

Pocono Home with Spa & Games near Skiing & Lake

We are so excited to welcome you to our home. Whether enjoying the peace and quiet from our private wrap around porch and local lake or taking a short ride to nearby skiing & hiking, this space is perfectly located for a unique getaway with family or friends. Watch deer and wildlife right from the comforts of our master bedroom balcony. Enjoy staying close enough to the thrills of everything the Poconos has to offer, yet far enough to kick up your feet at the community lake or in home spa.

5 out of 5 average rating, 118 reviews

Cabin in Tobyhanna

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.

A log-sided cabin is showcased amidst autumn foliage, featuring a set of welcoming steps leading to the entrance. The surrounding trees display vibrant fall colors, and sunlight filters through the branches, illuminating the exterior of the home and driveway.

4.91 out of 5 average rating, 213 reviews

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.

A spacious dining area features a large wooden table surrounded by tan chairs. A blue vase filled with greenery is centered on the table. The open-concept space is complemented by a cozy yellow sofa in the background and artwork on the dark wall.

5 out of 5 average rating, 127 reviews

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.

A rustic interior is showcased with wooden beams and warm tones. A dining area features a long table set for meals, while a cozy seating area with patterned cushions is present. A staircase leads to an upper loft, and a vintage-style lamp adds soft lighting.

4.89 out of 5 average rating, 236 reviews

The Gingerbread-Pocono cozy w/hot tub near lakes!

A magical & cozy cabin in the woods awaits! Remove the cares of the world. Soak in the inviting hot tub, tell stories round the campfire, play games around the table or spin discs on the record player! Central to all the amenities of Indian Mountain Lake you're also a short walk from Boulder lake it's great beach, kayaking, fishing, & swimming. A short drive gives you access to great hiking, skiing, shopping, restaurants, historic Jim Thorpe and the Pocono Raceway!

4.94 out of 5 average rating, 338 reviews

Guest house in Lititz

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

Cabin in East Stroudsburg

The cabin features a modern exterior with large windows and a dark finish, enhancing its rustic charm. A welcoming deck is accessed by steps, surrounded by natural landscaping. Warm lights are positioned above, providing subtle illumination for evening gatherings.

4.92 out of 5 average rating, 131 reviews

Gorgeous Lake Cabin in Poconos

The perfect escape from city life. Up winding mountain roads you'll land at your private cabin just a walk away from the beautiful lake. Enjoy our private hot tub or sit outside on our expansive deck & watch the wildlife. Gather around the firepit to make s'mores. If you're looking to be more active, there are basketball courts, tennis courts, & swimming all within our safe and peaceful gated community.

Superhost

Chalet in Tobyhanna

4.92 out of 5 average rating, 144 reviews

The | Kensington | Chalet

Welcome to The | Kensington | Chalet , a modern day cabin coupled country charm to create the perfect getaway . The home is fully equipped with all the necessities to make a comfortable stay such as 1000MBPS WIFI , laundry , a modern and easy to use kitchen . Our expansive outside patio is furnished with a 5-6 person hot tub , sauna , BBQ grill , lounger and seating furniture.