Holiday rentals in Winona Lakes

Poconos Lake Cottage. Hot Tub + Nature + Fire pit

Surrounded by peaceful forest this picturesque retreat is only 1hr30 from NYC and less than 2hrs from Philly! A sunny deck overlooks the lake and backyard filled with wildlife. This cottage has been designed with warm, stylish touches that emphasize comfort and relaxation. Enjoy a cozy fireplace, steamy hot tub, plenty of games, fast wifi, kayaks, SUPs. Minutes away: Shawnee Mountain(skiing),Breweries&Wineries, golfcourses and the Delaware National Rec area (hiking, biking, river excursions)!

Luxe 2-Bed/2.5-Bath: Sleeps 8, Breakfast/Ski/Views

Beautiful luxe townhouse for up to 8 guests, with 2 bedrooms, 2.5 baths, a full kitchen, office, loft, and a deck with a grill overlooking parklike shared grounds. Bright interiors, skylights, mountain views, and a marble master shower will take your breath away. Steps from Shawnee Mountain and a short drive to Shawnee Inn & Golf, Bushkill Falls, the Delaware Water Gap, outlets, and dining. Includes breakfast, snacks, and quality body care—ideal for families, couples, or groups. Decor available.

Cliffside Chalet

Located conveniently in the Pocono’s, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Escape to our newly renovated Chalet that was built on a rock ledge and features a gigantic 22 foot ceiling with a charming loft to relax in. Enjoy being surrounded by lush greenery and nature, just minutes from popular hiking trails, waterfalls, and walking distance to the lake and playground. The bathroom features rare stone imported from Italy and a sink carved out of rock boulders.

★Scenic Mountain Oasis | Mins to Ski Slopes/Hiking

Spoil yourself by staying in the modern townhouse nestled less than 5mins away from the ski slopes of Shawnee Mountain. Besides numerous winter activities, East Stroudsburg offers many hiking trails throughout lush green forest in the summertime. Enjoy the lovely natural ambiance in the backyard, or relax in the comfortable and stylish interior. ✔ 2 Comfy BRs, King and Queen sized, and a Queen Loft Bed ✔ Fully Equipped Kitchen ✔ Indoor Fireplace ✔ Workstation ✔ High-Speed Wi-Fi ✔ Free Parking

Entertainers Retreat • Fire Pit + Games • Hot Tub

Nestled within the Poconos mountains is this ultimate city escape packed with luxury amenities for the whole family to enjoy all just 5 mins from the ski slopes. Inside you’ll find open plan living with a Hamptons-style kitchen, 4 beautiful bedrooms and a fun games room, while outside you can enjoy the outdoor cinema, the social fire pit, BBQ’s, the luxe hot tub and so much more! Stay just 5 mins to Shawnee Ski Resort, the Country Club & Stroudsburg with its restaurants, shopping & attractions!

Norway Chalet: Forest Escape

Located Conveniently in the Pocono's, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Our relaxing A-Frame Chalet is inspired by European design/ architecture and gives you the feel of a Nordic Home in the Poconos. Enjoy 4 large decks where you can hear the birds chirping and watch humming birds, butterflies, deer, and other wildlife in a "jungle like" back yard. Just minutes from the most popular hiking destinations, and water falls. Pets are welcome free of charge (:

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

Coziest Creek Cabin- Idyllic, Authentic, Poconos

Deep within our psyche lies a romantic image, that of a log cabin tucked into the woods perched above a babbling trout laden stream. Perhaps inside there's a sheepskin rug laid before a grand fireplace, a reading nook, and a child's dreamy hideaway loft. Or maybe you're out on the deck, a crisp morning bundled and sipping cocoa on a rocking chair, or nights soaking sore bones and soaking up the sounds of the stream & kids below roasting smores by the fire. Now make that dream a reality!

Pocono Castle: Dungeon Escape Room & Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

5BR Lux Cabin w HotTub/Sauna/Pool/FirePit/GameRoom

Nestled within the Poconos mountains, this luxe 4,800+ SQ FT log cabin + resort-style amenities on 2 acres is the ultimate city escape and entertainment paradise. Fire pit, theater, bar/game room, 3 fireplaces, 8 TVs, kids bunk/playroom, 2 living rooms, gourmet kitchen, multiple decks/balcony & massive backyard. All this just minutes from skiing, hiking, great dining in Stroudsburg, Shawnee Mtn, Camelback Resort, and the Delaware Water Gap. The perfect getaway for families and large groups!

Luxury PA cabin, heated pool, hot tub, game r

This is a three floors gorgeous A FRAME HOUSE designed for anybody who loves nature, luxury homes, and privacy, with an amazing interior design cozy and modern. Is a private space for friends and families. During your visit you will have work space, pool, hot tub, pool table, game room, tv room, outdoor fire pit, indoor fireplace, back porch with an amazing view, modern kitchen, and cozy corners all around the house, It’s the perfect vacation rental home that you will never want to leave!

Luxury Pocono Retreat | Game Room • Pool • Firepit

The Penn House welcomes you to adventure 🌲 Just 90 minutes from NYC, this pet-friendly 4BR Pocono retreat offers a game room, firepit, spacious deck, and access to indoor heated pool, lakes, tennis & basketball. Six complimentary amenity fobs are provided; additional fobs are available for purchase at Guest Services. Minutes from skiing, waterfalls, hiking, ziplining & Camelback. Perfect for families, groups, and unforgettable escapes.