Vacation rentals in Winona Lakes

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Top-rated vacation rentals in Winona Lakes

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Guest favorite

Castle in East Stroudsburg

4.99 out of 5 average rating, 278 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!

Sep 19 – 26

G$134,192 GYD per night

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.

Nov 17 – 24

G$34,923 GYD per night

Guest favorite

Cottage in East Stroudsburg

4.99 out of 5 average rating, 203 reviews

Poconos ~Cottage in the Woods~

Cabin vibes & luxury touches make the ⇛Cottage in the Woods⇚ an amazing place for our guests! Come escape to the Cottage nestled deep in the woods in a peaceful and quiet area. Connect with nature watching roaming deer and woodland views from the 4 season sunroom. Enjoy an evening fireside at the firepit with friends and family. *YoutubeTV included* We invite you to our Cottage with cabin vibes & luxury touches. 90min from NYC and 2hrs from Philadelphia. Welcome to the Pocono Mountains!

May 10 – 17

G$29,083 GYD per night

Guest favorite

Guesthouse in Blairstown

4.97 out of 5 average rating, 203 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:

Jul 13 – 20

G$29,296 GYD per night

Superhost

Townhouse in East Stroudsburg

4.91 out of 5 average rating, 161 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

May 19 – 26

G$34,763 GYD per night

Guest favorite

Cabin in East Stroudsburg

4.92 out of 5 average rating, 118 reviews

Modern BLVCK Cabin 3 near Bushkill Fall Hot Tub

NEW BLVCK CABIN 3! True mountain escape with designer finishes and high end appliances. The Cabin is situated near Bushkill Falls. The house is suited for 8 people with 3 queen bedrooms and Queen 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 gas fire pit. Basement with cozy fireplace and projector. Only 20mins away from Shawnee Mountain and Bushkill Falls.

Jan 18 – 25

G$46,516 GYD per night

Guest favorite

Guest suite in Bangor

4.94 out of 5 average rating, 243 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.

Jun 6 – 13

G$27,673 GYD per night

Guest favorite

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

Apr 27 – May 4

G$30,031 GYD per night

Guest favorite

Apartment in Stroudsburg

4.85 out of 5 average rating, 155 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.

Apr 21 – 28

G$19,381 GYD per night

Guest favorite

Guesthouse in Stroudsburg

4.92 out of 5 average rating, 101 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.

Sep 26 – Oct 3

G$18,313 GYD per night

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

Sep 14 – 21

G$22,397 GYD per night

Guest favorite

Home in Bushkill

4.99 out of 5 average rating, 229 reviews

House on a Hill

This 3 bedroom house is great for anybody that wants to relax and have a good time, due to the many attractions close by. The house is 2 stories, the first floor has the living room, kitchen, bathroom, and two bedrooms. The second floor had the master bedroom including a master bathroom.

Aug 2 – 9

G$32,996 GYD per night