Holiday rentals with a pool in Monroe County

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.

Simply Serene: Wild West City, 4 acres of privacy

✨IT'S ALL ABOUT FINDING THE CALM IN THE CHAOS ✨ & making memories .. 🌿4 ACRES OF PRIVACY, TRANQUILITY & WILD WEST CHARM 🌿4 COZY BEDROOMS • 3000+ SQ FT OF PURE FUN 🏡Unique Custom Designed Retreat in the Heart of the Poconos - Stunning Nature & Wildlife yet Minutes from All Major Poconos' Attractions 💖Perfect for Any Group Size - From Romantic Getaways, to Family Reunions, Special Occasions, OR Relaxing with Friends & Loved Ones ⭐Over 100 Indoor & Outdoor FUN Activities for All Ages ⭐

Poconos - Blue Canoe Lakefront Retreat w/Spa Room

18 in of snow!!! 10 miles to Camelback. Welcome to The Blue Canoe, where lakefront luxury meets mountain adventure. Perfectly located near premier skiing this retreat offers the best of all seasons—kayak through misty mornings, relax at the community’s beach or pool, or enjoy serene afternoons on the water. Inside, indulge in a private spa-inspired suite, complete with a spacious two-person shower and relaxation room. Evenings bring cozy fireside gatherings, hot tub soaks under the stars.

Cozy Camelback Townhome - Ski In/Out Amazing View!

Welcome to High Pass Lodge! Freshly renovated & conveniently located on top of Camelback Mountain, within walking distance ski-in/out. Indoor heated pool, sauna, hot tub, & more for guests to enjoy (included with your stay). Close to Water Parks, Big Pocono State Park, Breweries, Casinos, Pocono Raceway, Shopping Outlets, Restaurants, & more activities for any season! Enjoy the breathtaking views from the deck while grilling, or cozy up in front of the living room fireplace, and Roku TV.

Pine Tree-House | Sleeps 8 | Hot tub

Get ready to experience the ultimate mountain retreat at Indian Mountain Lakes! Our cozy 2-bedroom home is perfect for families and friends looking for a winter or summer escape. Enjoy recently renovated interiors, comfortable bedding, and exciting amenities like a hot tub, WiFi, pool passes, lake access, fishing, playgrounds, tennis courts, basketball courts, and so much more! Amenity bracelets are $10/person for your entire stay and can be purchased at the pool house (21 Seneca Trail).

Cozy Dog Friendly chalet near Kalahari and Lakes

A Pocono Mountains retreat in Emerald Lakes. Black Bear Chalet is a cozy, family & dog friendly cabin which is close to Camelback, Kalahari, & Pocono Premium Outlets. Cozy up to the wood burning fireplace in the living room, firepit outside, enjoy some family games upstairs in the loft or prepare that delicious meal in the well equipped kitchen. Community amenity passes are available for purchase to enjoy the indoor & outdoor pools and beaches. Interior Christmas decor starting Dec 7th.

Hot Tub, Hammocks, Fire-Pit, Sunroom, Game Room!

Welcome to your one-of-a-kind mountain escape in Pocono Summit! This newly updated 3-bedroom, 2-bath home blends creative design with natural beauty—perfect for families, friends, or anyone seeking relaxation and adventure. Inside, unwind in the immersive illusion art game room. For outdoor explorers, use kayaks and paddle out on the nearby lake. With peaceful surroundingseasy access to Camelback Mountain, Kalahari Waterpark, and Big Pocono State Park, this is more than a stay.

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.

Peaceful Pocono Home-Close to Skiing + Jim Thorpe!

Welcome to Wild Antler Hideaway! Just a short walk away to the beautiful lake and amenities of Towamensing Trails and minutes to Jack Frost/Big Boulder, Hickory Run Trails, Jim Thorpe and More! The house comes with everything you need for a fun and relaxing stay including fully equipped kitchen, linens, propane grill, WiFi and Smart TVs. For entertainment, our outdoor games include horse shoe pit and cornhole and a variety of indoor board games.

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.

Rustic Private Ranch w/ Saltwater Pool & HotTub!

Escape to our newly remodeled secluded Modern Ranch home nestled in the heart of the Pocono Mountains! This luxurious 4 bedroom 2 bathroom retreat boasts, a living area. Relax in the spacious outdoor patio, outdoor dining area, & private lounge. Kickback around the reclaimed steel firepit under the stars. Book your getaway now and reconnect with nature in style. Roku Smart 4kTV in every room!

Secluded Hot Tub, Game Room x2, Lake Access, SUP

Nestled right by the lake in your own serene and secluded little forest glade, Lakeside Serenity offers a true retreat from all the hustle and bustle of everyday life. With 2 separate game room areas providing extensive gaming options, lake access just a stone’s throw away from your front door, and an extremely private back deck & hot tub, this spacious home will not disappoint! #LakeLife