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Vacation rentals in Winona Lakes

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Top-rated vacation rentals in Winona Lakes

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

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Guest favorite
A hot tub is positioned on a deck, offering views of a serene lake surrounded by vibrant foliage. The water appears inviting, and a shaded canopy provides protection from the sun. The tranquil environment enhances relaxation with natural scenery in the backdrop.
Cabin in East Stroudsburg
4.95 out of 5 average rating, 129 reviews

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)!

Top guest favorite
The exterior of a modern cabin is shown amidst a wooded landscape during twilight. Gravel surrounds the structure, and a patio is featured with a gas barbecue. Tall trees provide a natural backdrop, and warm light glows from the windows, hinting at a cozy interior.
Cabin in Cresco
4.98 out of 5 average rating, 172 reviews

The Little Black Cabin: Hot tub/Cold Plunge/Sauna

The Little Black Cabin (LBC) offers the perfect balance between rustic and lux. We remodeled this cabin with the goal to create a space where you can reconnect with nature while simultaneously indulging in pure comfort. It's a space designed to inspire, and to revitalize your mind, body and spirit - A place where you can chop wood, take a walk, light a fire, sit and relax under the stars, or enjoy a hot tub, cold plunge, or Finnish-style handmade sauna - We welcome you to The Little Black Cabin.

Top guest favorite
A spacious living area features high ceilings and large windows allowing natural light to fill the room. Comfortable seating is arranged around a soft rug, and a stylish staircase leads to a loft space overlooking the kitchen equipped with modern appliances and bar seating.
Townhouse in East Stroudsburg
4.92 out of 5 average rating, 145 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.

Guest favorite
An open living space showcases high wooden ceilings and large windows, allowing natural light to fill the area. A cozy seating arrangement is positioned beside an elegant dining table. A modern kitchen with a spacious island is visible, with a glimpse of lush greenery through the glass doors.
Chalet in East Stroudsburg
4.88 out of 5 average rating, 104 reviews

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.

Superhost
Townhouse in East Stroudsburg
4.88 out of 5 average rating, 212 reviews

★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

Guest favorite
The A-frame chalet is surrounded by lush greenery, featuring a welcoming front porch with steps leading to the entryway. Large windows allow ample natural light to fill the interior. A small shed is visible in the background, accentuating the tranquil forest setting.
Cabin in East Stroudsburg
4.94 out of 5 average rating, 201 reviews

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 (:

Guest favorite
Townhouse in East Stroudsburg
4.97 out of 5 average rating, 182 reviews

Serene Escape - Jacuzzi, mins from trails/skiing

Step into the comfort of this luxurious, 2 BR 2 Bath house with recently renovated spaces that make it feel like a home away from home. Situated in a serene residential area, the home promises a mountain retreat close to the best skiing, restaurants, stores, hiking, and amenities of the Poconos. Enjoy ski slope and mountain views from the deck. Contemporary design and an abundance of amenities will satisfy all your needs. ✔ 2 Comfortable BRs ✔ Fully Equipped Kitchen ✔ Jacuzzi Tub ✔ Smart TVs

Guest favorite
A stone fireplace serves as the focal point of the cozy living area, surrounded by wooden beams and walls. A sheepskin rug is placed in front of the fireplace, while a leather sofa and armchair offer comfortable seating. Natural light filters through the window, enhancing the rustic ambiance.
Cabin in East Stroudsburg
4.93 out of 5 average rating, 438 reviews

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!

Top guest favorite
Cabin in Mount Pocono
4.98 out of 5 average rating, 174 reviews

Poconos True Log Cabin| Views, Hot Tub & Game Room

Tucked away on 2 private acres overlooking a valley and creek, our log cabin is just 4 minutes from shopping and a short drive to Camelback, Kalahari, and Great Wolf Lodge. Plenty of space in the cozy living room, open loft, and outdoor areas. Enjoy the private hot tub on the spacious deck with stunning views, a pool table and ping pong table for indoor fun. Gather around the outdoor fire pit, or cozy up by the indoor fireplace. The warm of this true log cabin makes it a favorite year-round!

Top guest favorite
Castle in East Stroudsburg
4.99 out of 5 average rating, 454 reviews

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!

Top guest favorite
The cabin exterior is surrounded by tall trees, showcasing natural wood siding and a welcoming porch. A pair of yellow chairs are positioned on the porch, inviting relaxation. Large windows allow for ample natural light, enhancing the connection to the forested setting.
Cabin in Dingmans Ferry
5 out of 5 average rating, 347 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 favorite
Cabin in East Stroudsburg
4.96 out of 5 average rating, 269 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

Popular amenities for Winona Lakes vacation rentals