Holiday rentals in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

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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
4.97 out of 5 average rating, 155 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 favourite
A cabin nestled among trees features a wrap-around deck, enhancing the connection to nature. Large windows bring natural light into the space, with a stone chimney adding rustic charm. The surrounding area is covered in fallen leaves, indicating the seasonal surroundings.
Cabin in Bushkill
4.9 out of 5 average rating, 146 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 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, 390 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 serene outdoor seating area features two wooden chairs positioned beside a stone platform. A fire pit with a crackling flame is set in front of the chairs, overlooking a gently flowing creek and lush greenery, creating a tranquil nature retreat.
Cabin in Millrift
4.99 out of 5 average rating, 246 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, 417 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!

Guest favourite
An inviting living area features a comfortable white sofa adorned with decorative cushions. A plush armchair in dark purple contrasts with warm wood flooring. The kitchen, visible in the background, includes wooden cabinetry and modern appliances. Natural light brightens the space through a window.
Guest suite in Bangor
4.94 out of 5 average rating, 343 reviews

Modern Cozy Oasis-Mountains Retreat

Relax in a Modern, Cozy Apartment on a Scenic 3-Acre Retreat Unwind in this stylish and comfortable apartment set on 3-acre property with stunning mountainside views. Whether you're walking, jogging, or simply relaxing, the spacious yard offers the perfect setting to reconnect with nature. In the evenings, gather around the fire pit and enjoy the peaceful sounds of the outdoors. 5 mins to historic Bangor 25 mins to Poconos, Kalahari, ski resorts & Delaware Water Gap Escape & unwind!

Top guest favourite
Guest suite in Columbia
5 out of 5 average rating, 292 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 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, 349 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 favourite
Home in East Stroudsburg
4.98 out of 5 average rating, 165 reviews

Home away from home, with many community amenities

Make some memories in our unique and family-friendly cozy home. Our newly renovated clean home features: Modern bathrooms - one bathroom features a state of the art shower experience. Fully stocked kitchen New comfortable mattresses in themed bedrooms, one bedroom has a king size bed Backyard water feature Outdoor fairy garden Fire Pit Fire Pit Table Gas Grill All of this located in the number 1 rated amenity filled community in the Poconos featuring outstanding amenities.

Superhost
The living room features a cozy U-shaped sofa and a mounted flat-screen TV above a modern coffee table. Large windows illuminate the space, revealing views of the outdoor area. An indoor fireplace and telescope are present, adding charm to the inviting atmosphere.
Townhouse in East Stroudsburg
4.89 out of 5 average rating, 201 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 the 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 and Loft Bed ✔ Fully Equipped Kitchen ✔ Indoor Fireplace ✔ Workstation ✔ High-Speed Wi-Fi ✔ Free Parking

Guest favourite
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
4.85 out of 5 average rating, 334 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.

Top guest favourite
The exterior of the rustic cottage features a wooden facade and two sets of French doors. Chairs are positioned on a stone path leading to the entrance, surrounded by a manicured garden area with pebbles and greenery. Nearby trees provide a natural backdrop.
Guest house in Stroudsburg
4.95 out of 5 average rating, 231 reviews

Cozy guest cottage with indoor fireplace

Take it easy at this unique getaway in the Poconos! This vintage one room cottage is the perfect space for soaking in nature, getting creative, or exploring the attractions of the Pocono Mountains. The cozy cottage is within 20 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park. Reach downtown Stroudsburg and it’s restaurants and nightlife within 7 minutes.

Popular amenities for Winona Lakes holiday rentals