Holiday houses in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Castle in East Stroudsburg

4.99 out of 5 average rating, 281 reviews

Pocono Castle w/ Private Pond, Boat, Sauna,Hot Tub

No need to go to England to enjoy Castle life. We invite you to come and relax in this 2300 square-foot Castle home. It features four bedrooms, two full baths in a lovely Pocono setting.Enjoy the wildlife while relaxing in the outdoor hot tub or rejuvenate in Cedar Sauna. Indoor and outdoor games for all ages. Everyone will enjoy role-playing King & Queen, when dressing up in the costumes we provide. There is a 1 acre private pond if you would like to try your hand at catching your Golden Fish!

30 Sept – 7 Oct

$6,146 AUD total

Guest favourite

Farm stay in Blairstown

4.83 out of 5 average rating, 115 reviews

Cozy LakeView Farm near NYC/Rt.80 & Del. Water Gap

Enjoy Fresh Air & Spacious Views. Wildlife & Beauty Abound on this 80Ac Retreat w/Trails, Private Lake, Fields & Streams. Spread out in this wonderful open space. Ski & snow Tubing nearby. *Animal Tour w/Petting incl. See Guidebook for Seasonal Fun! Escape Pocono traffic & enjoy the countryside. *Close to NYC/Rt 80 thru a Quaint Moravian Village. Appalachian Trail access. Great local Farms & Markets w/Fresh Food. Alpaca & Wolf Preserve nearby. *3-day on Holiday. 1 dog only by approval <40 pnd

24 Sept – 1 Oct

$1,580 AUD total

Guest favourite

Loft in Andover

4.97 out of 5 average rating, 222 reviews

Private studio close to Sparta, Perona, Newton

You’ll love our private studio, accessed from its own entrance. Skylights and large windows overlook woods and create a peaceful, light, and airy feel. Close to Perona Farms (1.5 miles - 5 min drive), Lake Mohawk Country Club in Sparta (10 min drive), Sussex Fair Grounds ( 25 min drive), Mountain Creek Ski Resort ( 37 min drive). Beautiful walking, biking trails, scenic lakes. Sorry no children 12 and under. Refrigerator, small Microwave, Kuerig. Max 2 people. Welcome! John & Joan Thomas

11 – 18 Sept

$1,486 AUD total

Guest favourite

Guest suite in Bangor

4.97 out of 5 average rating, 264 reviews

Takes two private suite

Great price and NO CLEANING FEE! Welcome to our home just minutes away from shopping, hiking, skiing, snow tubing, wineries, and breweries. After it all, come home to your own beautiful living room to warm your soul in front of the fireplace. Relax in the two person jetted tub in your bathroom. Chill outside on the deck with a crackling fire, or melt away in the outside hot tub. When the time comes, rest your head on a soft queen bed in a spacious bedroom. Please no smoking or vaps on property

25 June – 2 July

$1,255 AUD total

Guest favourite

Cabin in East Stroudsburg

4.98 out of 5 average rating, 234 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!

25 Jan – 1 Feb

$5,482 AUD total

Superhost

Chalet in Lehman township

4.86 out of 5 average rating, 197 reviews

Quaint Chalet, quiet, clean, pet-friendly!

Remodeled chalet in the woods near hiking/biking trails and waterfalls in the 70,000 acre Delaware Water Gap National Recreation Area (house is a 10 minute walk from a park entrance/trails and lakes). Nearby community pool and tennis courts (both summer only). Kayaking/canoeing on the scenic Delaware River. Sit amongst the trees on the wrap-around deck and enjoy the sights and sounds of nature. Get cosy by the fireplace on cool evenings. Fully stocked kitchen, gas grill and linens provided.

5 – 12 Nov

$2,115 AUD total

Guest favourite

Guesthouse in Blairstown

4.97 out of 5 average rating, 204 reviews

Country Barn in Historic Northern NJ

Historic Hope NJ: 2 story country barn sleeps 1-4 people; New Kitchen & bath Loft has king bed & clothes storage. Second bedroom has double sized futon New outdoor deck seats 4; WiFi & cell phone access; Good for singles, couples, business travelers, visiting parents, kayakers, hikers, bicyclists, gliders, nature lovers, etc. Near Delaware Water Gap, Wolf Preserve, Farmer's Markets, Antiquing, Appalachian Trail, Nature Center, Land of Make Believe, Blairstown & Blair Academy:

11 – 18 Oct

$1,784 AUD total

Guest favourite

Cabin in Canadensis

4.91 out of 5 average rating, 878 reviews

Pocono Log Cabin Getaway

Cute & Cozy One Bedroom Log Cabin tucked away in the picturesque Pocono Mountains. Embrace the simplicity & tranquility of the mountains. Perfect for a cozy retreat. Private hot tub nestled in the trees, outdoor fireplace, hammock, and gas grill. The Pocono Mountains offer a diverse range of activities & attractions, including scenic hiking trails, thrilling ski slopes, lakes for boating & fishing, golf courses, water parks, charming towns w/shopping & dining options.

19 – 26 Feb

$2,042 AUD total

Guest favourite

Guest suite in Bangor

4.94 out of 5 average rating, 245 reviews

Modern Apt - Countryside /PoconoMountains/SKI

Soak up the modern and homey apartment surrounded by private 3 acres yard with mountain side views. Plenty of space to walk, run or sit and relax in a countryside atmosphere. Enjoy evenings by the fire pit and nature sounds in the background. Only 5 minutes from beautiful and historic town of Bangor. Near Pocono Mountains and Lehigh Valley attractions, within 25 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park.

28 May – 4 June

$1,681 AUD total

Guest favourite

Townhouse in East Stroudsburg

4.97 out of 5 average rating, 119 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 an mountain retreat close to the best restaurants, stores, and amenities of the Poconos. Contemporary design and an abundance of amenities will satisfy all your needs. ✔ 2 Comfortable BRs ✔ Fully Equipped Kitchen ✔ Jacuzzi Tub ✔ Smart TVs ✔ Free Parking

6 – 13 June

$2,022 AUD total

Guest favourite

Guesthouse in Stroudsburg

4.92 out of 5 average rating, 104 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.

7 – 14 Oct

$1,135 AUD total

Superhost

Home in East Stroudsburg

4.79 out of 5 average rating, 142 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."0

8 – 15 Mar

$1,423 AUD total