Vacation rentals in Winona Lakes

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Top-rated vacation rentals in Winona Lakes

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Top guest favorite

Castle in East Stroudsburg

4.99 out of 5 average rating, 375 reviews

Pocono Castle w/ Dungeon Escape Room &Private Pond

OMG! 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

Cabin in Monroe County

4.97 out of 5 average rating, 103 reviews

Pocono cabin and wild trout creek

NEW EARLY CHECK IN 9 AM ! We welcome people from all walks of life to visit us and enjoy this beautiful property and all that the Poconos has to offer. Set back in the woodlands, the cabin overlooks a designated class A wild trout creek that flows through a small ravine of indigenous flora and old growth trees. The cabins’ large deck offers a tree house view of it all! Our guests enjoy this cozy cabin and its’ long list of amenities. Come see what they are raving about. Guide book in the works.

Superhost

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

5 out of 5 average rating, 4 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

A spacious great room features tall ceilings with exposed beams, filled with natural light from large windows. Comfortable seating for eight is arranged around a coffee table. The view of the mountain range can be seen through the windows, enhancing the room's open atmosphere.

Home in East Stroudsburg

4.82 out of 5 average rating, 171 reviews

A minimal retreat atop the Pocono mountains.

Tucked away stands a private minimal retreat for those seeking to relax and recharge. Standing high above the tree tops, are 180 degrees of open mountain views from either of the two outdoor decks, or one of many windows that light Alpine. Alpine Cottage offers quick access to Camel Back or Shawnee mountains, hiking or kayaking on the Delaware, ATV, Snowmobile and waterfall tours, zip lining, and antique malls. Visit one of three indoor/outdoor resorts -Camelback, Kalahari or Great Wolf Lodge.

Guest favorite

A tranquil fire pit area is presented with two wooden Adirondack chairs positioned around a circular stone fire pit. A gravel path leads through a lush green landscape, bordered by a sturdy rock wall and surrounded by greenery.

Cabin in East Stroudsburg

4.97 out of 5 average rating, 105 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 (:

Top guest favorite

A vibrant waterfall cascades over rocky ledges, surrounded by lush green foliage. The water descends into a dark pool at the base, creating ripples and splashes. Sunlight filters through the trees, illuminating the serene scene in this peaceful natural setting.

Townhouse in East Stroudsburg

4.97 out of 5 average rating, 153 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 one-level cabin is nestled among trees, showcasing a wrap-around deck and large windows that illuminate the interior. The surrounding area features fallen leaves and natural stones, enhancing the connection to the forest environment.

Cabin in Bushkill

4.93 out of 5 average rating, 123 reviews

Whimsical Forest Retreat near Bushkill Falls

PLEASE SELECT "SHOW MORE" TO SEE FAQ AT BOTTOM FOR INFO ABOUT PET POLICY, FIREWOOD, AND MORE. Come stay at our forest-fantasy abode in the Poconos, where each bedroom is inspired by the seasons. Enjoy the wrap-around deck, picnic table surrounded by trees, and smoker/grill. We have a washer/dryer, full kitchen, and 2 full baths. We’re located nearby Bushkill Falls (10 min), Shawnee Mountain (15 min), Delaware Water Gap (20 min). The home is in a gated community with many guest amenities.

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

4.94 out of 5 average rating, 352 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!

Guest favorite

A spacious living area is illuminated by natural light from skylights and large windows. The space features a comfortable seating area with a sectional sofa, a dining table for six, and hardwood flooring. Greenery is present, adding a touch of nature to the interior.

Cabin in Stroudsburg

4.87 out of 5 average rating, 327 reviews

El Sol~A Cozy/Trendy Cabin With Stunning Views!

This peaceful, beautiful, SUNNY and cozy cabin is the perfect escape! A winter Ski retreat only 15 minutes to Shawnee Mountain and all the outdoor activities. So much light and a wall of windows looking out into the woods and surrounding mountains. 2 bedrooms, 3 beds 1 and 1/2 bath. Only a short drive from NYC or Philly and within 10 mins from camping, hiking, rafting and fishing in the spring and summer months. El Sol is a magical and perfect homey place for a day off or extended vaca!

Top guest favorite

Guest suite in Columbia

5 out of 5 average rating, 273 reviews

DWG Country Mountain Oasis-Frog Pond View

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 favorite

A rustic fire pit area is illuminated by soft string lights, creating a warm ambiance at night. Five red Adirondack chairs are arranged around a circular stone fire pit, surrounded by greenery and gravel pathways, offering a cozy gathering spot in nature.

Cabin in East Stroudsburg

4.88 out of 5 average rating, 143 reviews

Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub

Welcome to our cozy cabin near Bushkill Falls! This cozy retreat offers beautiful wood burning hot tub and fire pit. More so, there are three spacious bedrooms, you and your loved ones can comfortably unwind after a day of exploration. The open concept kitchen, equipped with modern appliances provides a seamless cooking experience. For entertainment enthusiasts the cabin features a projector room. Step outside onto the balconies and be captivated by the picturesque views of the nature.

Guest favorite

Townhouse in East Stroudsburg

4.95 out of 5 average rating, 243 reviews

Whitetail House-Hiking, Biking & River adventure

Our house is located just up the road from the Shawnee Mountain Ski Area. Located between Bushkill Falls and the Delaware National Recreation Area offers hiking, biking, rivers, streams, and waterfalls. From Spring to Fall, easy access to kayak or canoe rentals. Numerous golf courses are just minutes away. The historical town of Delaware Water Gap and Stroudsburg offers a variety of restaurants, music venues, wineries, and boutiques. Best of all, we are only 75 minutes west of NYC.