Holiday rentals in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cabin in East Stroudsburg
5 out of 5 average rating, 101 reviews

Cozy Lakeside Cottage w Year Round Hot Tub

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)!

Top guest favourite
A modern bathroom features a glass shower with marble tiles, a freestanding tub beside a window, and plush towels hanging nearby. The light wood flooring complements the spacious layout and natural light filters through a skylight.
Townhouse in East Stroudsburg
4.94 out of 5 average rating, 124 reviews

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.

Top guest favourite
A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.
Castle in East Stroudsburg
4.99 out of 5 average rating, 431 reviews

Pocono Castle w/ 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!

Top guest favourite
A rustic wooden cabin is nestled among tall trees in a dense forest. A covered front porch is visible, featuring two yellow chairs and surrounded by natural landscaping. The cabin's exterior showcases a blend of wood tones and large windows, inviting natural light indoors.
Cabin in Dingmans Ferry
5 out of 5 average rating, 336 reviews

Charming Chestnut Cabin in Woods

*Winter bookings must have 4 Wheel or AWD Vehicle. This one-of-a-kind cabin borders the Delaware Water Gap National Recreation Area. Hike right behind the cabin, through the woods, to Dingmans Creek. A short hike upstream leads to George W. Childs Park with 3 tumbling waterfalls, a rustic trail system, and observation decks. A longer hike downstream will bring you to Dingmans Falls. DWGNRA offers swimming, fishing, hiking, biking, canoeing, and kayaking, all within minutes of the cabin.

Top guest favourite
A log cabin is shown nestled among trees, with a gravel area in front and a natural stone border. A deer is visible nearby, highlighting the serene natural surroundings. The sky features a gradient of warm colors, creating a peaceful ambiance.
Cabin in East Stroudsburg
4.95 out of 5 average rating, 234 reviews

Creekfront Poconos Cabin w/ Hot Tub & Fire Pit

Welcome to Split Creek Cabin, a private creekfront retreat nestled down a quiet dirt road along Marshall’s Creek. This cozy 2-bedroom, 1.5-bath log cabin offers a one-of-a-kind Poconos experience combining rustic charm with modern comfort. Unwind in the hot tub as the soothing sounds of the creek flow by, roast s’mores around the fire pit under starry skies, and enjoy a relaxing escape where your only neighbors are towering trees and wandering deer. A cozy, Creekside stay you won’t forget

Top guest favourite
Guest suite in Columbia
5 out of 5 average rating, 295 reviews

DWG Mountain Oasis-Private Apt w/Frog Pond

Private family apartment built for relaxing comfort and views of nature 2 miles from Mount Tammany, Mount Minsi, and the Appalachian Trail Walk to a private brookside trail and a winery Private deck Includes: Bread, eggs, pancake mix, coffee, tea, milk, bananas, s'mores kit, and more AWARDS: Top 1% of all Airbnb & #1 "Most Hospitable NJ Host" in 2021 Little or no host interaction – your choice Host lives on-site and can provide customized recommendations for food and things to do

Guest favourite
The open living area features a high ceiling with wooden beams and large windows allowing natural light to fill the space. An American flag is displayed prominently on the wall above a stone fireplace, surrounded by cozy seating and a dining area with a table.
Cabin in East Stroudsburg
4.83 out of 5 average rating, 108 reviews

Modern Creekside cabin near falls, slopes & more!

Welcome to Bushkill River front cabin! Literally steps from the Bushkill Creek and nestled away on a private road of unique log cabins. Enjoy a weekend getaway or long relaxing vacation in this lovely custom built cabin. This home will leave you feeling disconnected from everyday life yet is conveniently located to major roadways, golf, skiing, shopping and area attractions. If you are looking to enjoy the natural beauty of nature in a unique modern home—you have found it!

Superhost
The exterior of a modern cabin is viewed from above, featuring large glass windows with triangular accents. A spacious deck is highlighted by a dining table, lounge seating, and a hot tub. Surrounding nature is visible, revealing a carpet of fallen leaves.
Cabin in East Stroudsburg
4.84 out of 5 average rating, 353 reviews

BLVCKCabin2 near Falls w/HotTub, Sauna & Game Room

True mountain escape with designer finishes and high end appliances. The Cabin is situated near Bushkill Falls surrounded by a creek accessible for kayaking and fishing. The house is suited for 6 people 2 queen bedrooms on the main level and King Loft on the upper level. Open kitchen plan that connects with the living space highlighted by a beautiful fireplace. Beautiful deck for entertaining with a fire pit. Only 20mins away from Shawnee Mountain & 24/7 Supermarket.

Guest favourite
A spacious bedroom is depicted, featuring two large beds with crisp white linens and green woven bedskirts. Natural light floods the room through two windows. A wooden nightstand and a comfortable chair adorn the area, enhancing the welcoming yet simple design.
Guest suite in Mount Pocono
4.87 out of 5 average rating, 335 reviews

Nature Lovers Paradise Private Close to Everything

Many Pocono attractions within a 15 minute drive! Kalahari indoor water park 10 minutes away, Camelback Ski Area (with snowboarding and snow tubing) and Aquatopia indoor water park 15 minutes away, the Crossings Premium shopping outlets 12 minutes away, Blue Ridge Estates Winery, many restaurants & Mount Airy Casino and golf course is only 3 minutes away! 6 minutes to Sanofi. Large bedroom, big living space with microwave, fridge, deck with gas grill.

Top guest favourite
A charming red cottage is situated among lush greenery, featuring a spacious deck with wooden railings. Large windows are visible, inviting natural light into the interior. Steps lead up to the entrance, complementing the overall welcoming design of the property.
Cottage in Dingmans Ferry
4.96 out of 5 average rating, 451 reviews

The Upper Hill Cottage

Located in the heart of the Poconos, Just 1 hour and 15 minutes from Manhattan! Our home has been completely remodeled with no detail overlooked. Modern amenities, quiet community and minutes to hiking, waterfalls & the Delaware river. Pets welcome! ** Please take note** ALL DOGS MUST BE KEPT ON A LEASH OUTSIDE & ONLY ON OUR PROPERTY AT ALL TIMES! We have neighbors with animals and ask this for everyone’s safety. Thank you in advance!!

Guest favourite
Home in East Stroudsburg
4.96 out of 5 average rating, 136 reviews

Poconos Cabin | Hot Tub | Game Room | Pets | Ski

Escape to this luxurious Poconos getaway at The Alpine Haus the perfect place for families or couples seeking a perfect blend of relaxation and adventure. Enjoy a Hot tub, Fire pit, Smart TVs and central heating in this spacious 2060 Sq ft main cabin just a 12 min drive to Hidden Lake with easy access to nearby attractions like Delaware Water Gap Bushkill Falls and Shawnee for skiing golfing and rafting all in East Stroudsburg PA.

Guest favourite
The classic A-frame house is framed by lush greenery, featuring a vibrant green exterior and large windows that invite natural light. A wooden deck surrounds the entrance, complemented by two red chairs, creating a welcoming space for relaxation amidst the serene wooded environment.
Cabin in Pocono Pines
4.95 out of 5 average rating, 162 reviews

Pocono - A-Frame - Sauna, Hot Tub, Fire Pit

Escape to the idyllic surroundings of Pocono Lake and discover your perfect retreat at our classic A-frame home. Nestled in a serene wooded area on Lake Naomi (members only lake - not public), this true gem is the perfect spot for weekend getaways or remote work retreats. Whether you're looking for adventure or relaxation, our home has something for everyone.

Popular amenities for Winona Lakes holiday rentals