Vacation rentals in Winona Lakes

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Top-rated vacation rentals in Winona Lakes

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Top guest favorite

A wooden deck extends around the home, featuring outdoor seating arrangements and an umbrella for shade. Soft lighting enhances the brick exterior, while natural surroundings provide a serene backdrop. The sloped roof and large windows invite light into the cozy atmosphere.

Home in Bushkill

4.99 out of 5 average rating, 151 reviews

Raccoon Retreat

Hi, Welcome to Raccoon Retreat! This is a house that you will be able to come to unplug, unwind and reconnect with family, friends and all of what nature has to offer. The home is located within the ‪Delaware Water Gap National Recreation Area‬. Here you will have the opportunity to take advantage of hiking trails, waterfalls, swimming, zip lining, fishing, horseback riding, canoeing and kayaking, as well as skiing or snowtubing during the snowy season. Though you get to experience nature here, you are only a short drive away from restaurants, casino, shopping and also water parks. The entire home is all yours! Our three story home sits on a one acre wooded lot. In the event you are just wanting to get away to hunker down here, we have designed the space to feel cozy and warm. You will find a full kitchen ready for you to prepare some home cooked meals, three bedrooms, two baths, a soaker tub and a deck for miles! The home has a private driveway with plenty of space for up to 5 vehicles. Follow us on Instagram @raccoonretreat While you are enjoying your stay we will be available for you to contact as you need us anytime from afar. Please respect our home. A lot of heart has gone into creating this space and the hope is every new guest will get to enjoy the space as if they were the first!

Top guest favorite

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, 380 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

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

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

4.97 out of 5 average rating, 109 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 warmly decorated living area features a sectional sofa complemented by a plush ottoman. A natural wood accent wall houses a flat-screen TV above a fireplace. A potted plant adds a touch of greenery, while a patterned rug covers the wooden floor, enhancing the space's comfort.

Townhouse in East Stroudsburg

4.97 out of 5 average rating, 157 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

The inviting living area features wooden beams and a stone fireplace, surrounded by comfortable seating arrangements. Large windows illuminate the space, showcasing rustic decor and a cozy sheepskin rug on warm-toned wooden floors. A dining table is visible in the background, enhancing the communal atmosphere.

Cabin in East Stroudsburg

4.94 out of 5 average rating, 357 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

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, 294 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.

Guest favorite

The open living area features a spacious sectional couch, a wooden coffee table, and large windows that allow sunlight to illuminate the space. A dining table is visible in the background, along with a fully equipped kitchen, creating a welcoming and functional environment.

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

A landscaped garden features a winding pond surrounded by various plants and flowers. Smooth stones line the water's edge, adding natural texture. A small shed is visible in the background, framed by lush green trees, creating a serene and relaxing outdoor space.

Guest suite in Columbia

5 out of 5 average rating, 276 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 wood-burning hot tub emits a calming blue glow, surrounded by rustic seating. Red Adirondack chairs are arranged around a fire pit, positioned beneath warm string lights that enhance the outdoor ambiance, creating a relaxed gathering space beneath the night sky.

Cabin in East Stroudsburg

4.88 out of 5 average rating, 144 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

A spacious dining area features a dark wooden table with seating for several guests, complemented by metal chairs. The kitchen island, with modern stools, opens to the living room, which includes a fireplace and large windows overlooking a natural setting. Decorative red lights hang above.

Townhouse in East Stroudsburg

4.88 out of 5 average rating, 330 reviews

Magnolia House-Jacuzzi, Hiking, Biking & River

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

Top guest favorite

The house is surrounded by vibrant autumn foliage, showcasing a blend of greens, yellows, and oranges. A stone path leads to the entrance, framed by lush shrubs. The natural setting provides a serene and secluded atmosphere, with large trees creating a sense of privacy.

Home in Barrett Township

4.98 out of 5 average rating, 125 reviews

Rustic Poconos Cabin • Fire Pit • 2BR Retreat

Grotto Grove is a 2 bedroom, 1.5 bathroom house that sits on 6 private acres nestled between Skytop Lodge and Buck Hill Falls. We are 2 hrs away from both NYC and Philly. Perfect for friends and family looking to escape and reconnect or couples looking for a romantic getaway. Be it hiking our private trails in the summer, bird watching in the spring, or sitting around the wood burning stove with some apple cider donuts in the fall, if you love nature you will love Grotto Grove!