Holiday rentals in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

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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
4.94 out of 5 average rating, 109 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
4.96 out of 5 average rating, 169 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 spacious living and dining area features a blend of comfortable furniture, including a green armchair and a sleek table with chairs. A small decorative rug lies on the tiled floor, and a television is mounted on the wall. Natural light enters through a window, accentuating the room's warmth.
Guest suite in Hackettstown
4.88 out of 5 average rating, 145 reviews

Full Apartment near Hackettstown

Enjoy this private apartment connected to an 18th century stone house. It comes furnished with 1 1/2 bathrooms, a fully equipped kitchen, large living/dining room, and one bedroom with closet and a queen sized bed. We are located in the beautiful highlands of northwest NJ--about 60 miles from Lincoln Tunnel and 75 miles from Philadelphia. Nearby are historical sights, great hiking and skiing areas restaurants, brew pubs, and a train station. Private parking provided next to entrance.

Top 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, 353 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, 172 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.

Top guest favourite
A well-organized bedroom features a queen bed dressed in a patterned coverlet with animal motifs. Two nightstands with lamps flank the bed. Natural light enters through the large window, complemented by white blinds. A door and wall decor add warmth to the inviting space.
Guest house in East Stroudsburg
4.95 out of 5 average rating, 176 reviews

Cassie's Cozy Cottage- Poconos Near Shawnee

Welcome to Cassie's Cozy Cottage! Enjoy a peaceful stay suited for two people. Located near various outdoor recreational activities like skiing/snowboarding, hiking trails, river activities, golf courses, and also shopping outlets. Shawnee Mountain-3.7 miles, Camelback Mountain-12 miles, Delaware River Access- (Smithfield beach) 4.6 miles (Bushkill Access) 14 miles, Bushkill Falls- 10 miles. The Crossings Premium Outlets- 10 miles, ...and many more areas to visit close by.

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
4.88 out of 5 average rating, 207 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
Cabin in East Stroudsburg
4.83 out of 5 average rating, 279 reviews

BLVE Cabin-w/HotTub&Game Room near Bushkill Falls

True mountain escape! The BLVE Cabin is near Bushkill Falls & Shawnee Mountain. Sleeps 8 with 3 queen beds and a sofa bed. Enjoy the open kitchen & living area with an electric fireplace and nature views. Main deck offers BBQ, outdoor TV & gas firepit. Lower deck features a wood-burning hot tub. Game room with pellet stove, projector, ping pong & board games. Outside, relax by the real wood firepit, swing in the hammock & take in the peaceful mountain vibes.

Top guest favourite
The living area showcases a spacious layout with hardwood floors and large windows allowing natural light to flood the space. A black sofa is positioned near the double-height ceiling under a skylight, enhancing the open feel of the room. A staircase leads to additional areas.
Home in East Stroudsburg
4.85 out of 5 average rating, 223 reviews

Quiet rustic house/Jacuzzi in safe gated community

"Enjoy this beautiful spacious home that is located in a secured gated community, Indoor jacuzzi tub in the master bedroom on the second floor , the jacuzzi is a lay down tub for 2 people max .There is free parking on the premises, the driveway can hold up to 5 vehicles. The home is equipped with fast high speed WiFi that can be access all around the home." I have air conditioners in the top 2 floor bedrooms, the house stays cool in summer as well

Guest favourite
The cabin features a modern exterior with large windows and a dark finish, enhancing its rustic charm. A welcoming deck is accessed by steps, surrounded by natural landscaping. Warm lights are positioned above, providing subtle illumination for evening gatherings.
Cabin in East Stroudsburg
4.93 out of 5 average rating, 126 reviews

Gorgeous Lake Cabin in Poconos

The perfect escape from city life. Up winding mountain roads you'll land at your private cabin just a walk away from the beautiful lake. Enjoy our private hot tub or sit outside on our expansive deck & watch the wildlife. Gather around the firepit to make s'mores while you watch the sun set behind the mountain. If you're looking to be more active, there is a fitness center, tennis courts, & swimming all within our safe and peaceful gated community.

Superhost
A cozy bedroom features a spacious bed with a light blue comforter and decorative pillows. Two bedside tables with lamps flank the bed, providing soft illumination. A wall-mounted air conditioning unit is positioned nearby, and the carpeted floor adds a comfortable touch.
Flat in Stroudsburg
4.81 out of 5 average rating, 234 reviews

Stroudsburg - Poconos: Nice 1 bedroom

You will be staying within walking distance of many local shops and restaurants when you book this unit for your stay. You will be located in Stroudsburg which is very convenient and you will love the fact you will not have to search for parking. The apartment has everything you need to offer you a great experience. As your host, we make sure to offer you a comfortable place as well as respond quickly to any concerns or help you may need.

Guest favourite
A wooden dining table is surrounded by three chairs and a bench, set against a backdrop of large sliding doors leading to a deck. Natural light filters in through sheer white curtains, highlighting the tree views outside. Framed art decorates the wall beside a window.
Cabin in East Stroudsburg
4.91 out of 5 average rating, 139 reviews

Nature serene Cabin near popular hiking/waterfalls

Your trailhead starts here. Experience a unique stay surrounded by nature and sunset serenity. Thoughtfully remodeled and furnished for coziness and comfort in mind, this place is perfect for gatherings with family and friends, or a mere relaxing stay with a partner. The highlight of this place is the sunroom, accompanied by an entertainment room, providing the essentials for your enjoyment.

Popular amenities for Winona Lakes holiday rentals