Holiday rentals with a pool in Coolbaugh Township

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.

Peaceful Pocono Getaway - Fresh Air and Fun

Vaulted ceilings, living room fireplace, 2 first floor bedrooms in this airy and private 4-season cabin with easy access to the amenities in the area. The house is a short walking distance to the indoor pool (open Labor Day to Memorial Day), and just a street away from a beautiful state park with over 2000 acres to explore with trails and a sandy beach 250 acre lake. The outdoor pool, beaches, tennis courts and more are open Memorial Day to Labor Day. 3 Ski slopes are less than 30 minutes away.

Modern Rustic Private Ranch w/ Saltwater Hot tub

Escape the hustle of the big city in style at this picture-perfect open floor plan Modern Ranch Home, nestled in nature surrounded by 1.5 acres of breathtaking native white birch trees. The Ranch house offers a one-of-a-kind modern rustic aesthetic from the pro design team at Restoration Hardware. Full kitchen, king-size master bedroom, indoor fireplace, indoor & outdoor dining area, outdoor lounge, rustic chiminea-style firepit. There’s something for the whole family (including furry friends).

1 Minute Walk to Lake! Hot Tub. Sauna. Game Room.

Latitude Adjustment is a unique retreat in Pocono Lake, designed for those who seek the perfect blend of relaxation and local exploration. Equipped with an amazing 4person outdoor steam sauna, a private 7person hot tub featuring waterfall, Bluetooth speakers, and LED lights, huge game room with 65” TV, wood burning stove, large outdoor entertaining area with a grill, fire pit, guest shed and dining area. Located in a beautiful, amenity-rich Arrowhead Lake community, 1 minute walk to the lake!

Serene & Fun Family Gem ~ Hot Tub & Theater Room!

Look no further! This majestic 3BR 3Bath luxury cabin, ideally nestled on a secluded lot in the Big Bass Lake Community in the heart of Pocono Mountains. It promises a high-end family oasis a few mins from picturesque lakes, exciting attractions, and breathtaking natural landmarks. ✔ Large Private Hot Tub ✔ Game & Theater Room ✔ 3 Comfortable Bedrooms ✔ Living Room ✔ Full Kitchen ✔ Charcoal Grill ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Community Amenities (Pools, Lakes, & More) See more below!

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.

Poconos Lodge Retreat in Private Lake Community

The Lyman Lodge is a cozy retreat nestled in Big Bass Lake, a premier resort community in the Poconos. Enjoy all the region has to offer while relaxing with high-end comforts. Community amenities include lake access, indoor/outdoor pools, tennis, basketball, and pickleball courts, playgrounds, a splash pad, and fitness center. Lyman Lodge is also conveniently located near top Poconos attractions for year-round fun. Unwind and explore at the Lyman Lodge—your cozy Poconos hideaway!

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.

Hot Tub, Lake, Beach and Hiking!

Our cute Pocono Lake cabin is a dream come true for anyone looking for a private lake retreat. Pinewood Place is ideal for couples, families, or close groups of friends – and is close to all of the major attractions in the Poconos! Beyond the cabin itself, Pinewood Place is part of Arrowhead Lake, one of the leading privately owned, gated communities in the scenic Pocono Mountains. ***IMPORTANT: Please read Other Things to Note section prior to booking***

Creekside Cabin + short walk to lake & pool

LITTLE POCONOS CABIN Come unwind in our fully renovated cabin with a beautiful creek right in the backyard! Short walk to the lake, pool, canoe/kayak rentals, playground + state game lands Perfect for couples and small family groups *20-35 mins to hiking, waterfalls, golf, Camelback, Kalahari, Jack Frost/Big Boulder, Pocono Raceway, Mt Airy and Outlets* COMMUNITY AMENITIES: FOUR BEACHES, THREE POOLS, FISHING, GYM, GAME ROOMS

Ski In/Out JackFrost Townhouse w Fireplace

You may have just found your perfect Mountainside Retreat at Jack Frost! This newly renovated, ski-in/ski-out townhouse is a cozy base for any Pocono adventure. With comfortable bedding for 6 guests, and occupancy up to 8 guests, it features a wood-burning fireplace, a fully equipped kitchen, an EV charger, and summer lake club access. Enjoy modern comforts and direct slope access for an unforgettable getaway from the city.

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.