Holiday rentals in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

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Top guest favourite
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, 164 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!

Guest favourite
Cabin in East Stroudsburg
4.99 out of 5 average rating, 115 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
4.92 out of 5 average rating, 136 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 favourite
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
4.95 out of 5 average rating, 190 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 favourite
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
4.93 out of 5 average rating, 426 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 favourite
A cozy cabin is set amidst a lush forest, featuring a wrap-around wooden deck that invites outdoor relaxation. A stone pathway leads to the entrance, surrounded by vibrant green grass and trees, creating a tranquil atmosphere.
Cabin in Millrift
4.99 out of 5 average rating, 267 reviews

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

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, 442 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 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, 252 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, 299 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
A spacious living area features large windows allowing natural light to illuminate the room. A comfortable sofa is paired with leather bean bags, while a wooden coffee table sits on a decorative rug. Neutral walls and wooden beams create a calming atmosphere.
Cabin in Knowlton Township
4.98 out of 5 average rating, 109 reviews

Luxury forest cabin w/private trails

Welcome to picturesque spacious luxury: this fully renovated cabin, tucked away on an expansive 200+ acre property w/ private trails. The spectacular 1 bedroom features: vaulted ceilings, brand new kitchen/appliances, granite counter island w/seating, dining room, powder room & bathroom with walk in shower & soaking bathtub, King bed, blackout curtains, large windows w/ nature views, Smart TV, BBQ, hot tub option(available in May) & direct access to the serene forest & walking paths.

Guest favourite
Home in East Stroudsburg
4.93 out of 5 average rating, 110 reviews

Spacious 3BR Private Ski house- 10 min to slopes

Discover our charming mountain retreat, perfect for families and friends. Our 4-bed, 2-bath home boasts a new renovation, large open kitchen and dining area, and a spacious deck with outdoor grill and fire pit. Enjoy mountain views and privacy, just a short drive from Poconos attractions like Camelback Ski Resort, Kalahari Water Park, Great Wolf Lodge, Golf courses, a Casino and more. Relax and create memories with loved ones in our beautiful mountain getaway.

Top guest favourite
The cabin's A-frame structure is framed by lush trees, featuring a large glass front that invites natural light. A wooden deck with two yellow chairs offers a vibrant seating area. Potted plants add greenery around the entrance, creating an inviting outdoor space.
Cabin in Greentown
4.9 out of 5 average rating, 348 reviews

the little A, by camp caitlin

The perfect place for to wake up in the trees or spend a weekend with friends! Relax in tranquility and scenic beauty from your own porch! Surrounded by state land just minutes from numerous hiking trails and waterfalls in promised land state park. Enjoy a dip in one of the nearby lakes or toasty fire on a cold night inside by the wood stove.

Popular amenities for Winona Lakes holiday rentals