Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Guest favourite
A spacious kitchen is highlighted by a large island with a polished countertop, surrounded by wooden cabinetry. Pendant lights hang above, providing illumination. In the background, a dining area is visible, featuring a dark wood table with chairs, and a stone fireplace enhances the rustic charm.
Home in Moscow
5 out of 5 average rating, 14 reviews

Forest Lake Log House

Welcome to our log home on a private lake. No HOA, no gates, just privacy. It offers the perfect escape into nature while retaining a sense of tranquility and rustic charm. Set against the backdrop of Pennsylvania's lush forests, this picturesque home combines the timeless beauty of log construction with modern amenities, making it the ideal retreat for those seeking peace and privacy. If you’re seeking a weekend or week long getaway, this is a place to make memories that will last a lifetime.

Superhost
Chalet in Big Bass Lake
5 out of 5 average rating, 4 reviews

Lakefront Oasis w/ Speakeasy·Kayaks·HotTub·FirePit

Escape to Larsen Lake Lodge - a stunningly beautiful lakefront Pocono retreat unlike any other. Kayak or canoe right from your backyard, soak in the lake-view hot tub, kick back in the hanging egg chairs, gather round the lakeside fire pit or slip into the speakeasy game room for a night of fun. 🏖️ Steps to beach & tennis courts 🏊 4 min. to splash pad, pool & clubhouse 🛝 25 min to Kalahari & Camelback Resorts 🎰 30 min to Mount Airy Casino Experience the Poconos with us & learn more below!

Guest favourite
Cabin in Lake Harmony
4.93 out of 5 average rating, 213 reviews

"The Lure" Delightful, Private Waterfront Getaway

The Lure is a fully renovated 1940s fishing cabin reimagined into romantic waterfront retreat for 2 on the glacial waters of Round Pond in Lake Harmony. Designed for couples, this home pairs vintage charm with modern indulgence--private hot tub beneath the stars, crackling wood-burning fireplace, fire lit evenings by the shore, and quiet mornings drifting by canoe. Secluded yet moments from adventure: hiking, dining, skiing, Jim Thorpe, and Pocono Raceway--where romance lingers and time slows.

Guest favourite
Cabin in Gouldsboro
4.88 out of 5 average rating, 94 reviews

outdoor movie room private hot tub firepit by lake

*OLYMPIC SIZED POOL & AQUATIC CENTER OPENS JUNE 25!* Welcome to your dream escape in the heart of the Poconos! Experience outdoor movie magic on your 75-inch TV with fresh, homemade popcorn, or soak away stress in the bubbling hot tub after a day of exploring. Enjoy smores, stories and stargazing by the firepit after showing off your BBQ grilling skills! Designed to offer an unforgettable escape with a blend of luxury and nature, this cabin is ideal for families, couples, or friend groups.

Top guest favourite
The inviting entrance of the two-story farmhouse displays a yellow exterior with white trim. A small porch is accessible via a ramp, lined with potted plants and colorful flowers. A welcome flag is prominently positioned in the grassy area, adding a cheerful touch to the entrance.
Home in The Hideout
4.93 out of 5 average rating, 123 reviews

They call me Mellow/ Countryside Farm view

A lovely spot to relax in the rural countryside. Enjoy the fresh country air and observe the neighboring livestock. 6 miles to Lake Wallenpaupack. Nearby hiking trails at Lacawac Sanctuary, Schumans point and Varden conservation . Horseback riding at Why-Not riding stable. Antique shops and boutiques in historic Hawley and Honesdale. Under 30 miles to Montage Mountain Resorts, Elk Mountain, Ski Big Bear and Shawnee Mountain Ski Area. All bedrooms are on 2nd floor. Full bath on 1st floor.

Top guest favourite
A modern lakefront home is positioned within a wooded landscape, featuring floor-to-ceiling windows that provide a panoramic view of the surroundings. The exterior is surrounded by lush greenery, including ferns and large rocks, enhancing the natural setting. A deck extends from the home, inviting outdoor enjoyment.
Home in Greentown
4.98 out of 5 average rating, 54 reviews

Camp Double Oak | Modern Lakeside Retreat

Find your sanctuary at Camp Double Oak, where the peaceful embrace of nature meets the finest in luxury living. Nestled deep within serene woodlands of Northeast Pennsylvania's Pocono Mountains, this 3-bedroom 2-bath lakefront home offers one-of-a-kind experience. ✔ Lakefront ✔ Luxury Design ✔ 2h -> New York/Philadelphia ✔ Chef’s Kitchen ✔ EV Charger ✔ Kayaking ✔ Fire pit ✔ Grill ✔ High-Speed Internet 1.2 Gig Add my home to your Wishlist by clicking the ❤ in the upper-right corner.

Superhost
Cabin in Blakeslee
New place to stay

A-Frame ~ Explore ~ Hike and Bike ~ One of a Kind

A one-of-a-kind A-Frame filled with character and cozy spaces. Perfect for active outdoor enthusiasts looking to slow down and reconnect with nature. • Unique rustic design with warm mountain-lodge charm • Peaceful wooded setting with abundant natural light • Primary suite with serene forest views • Fire pit with custom seating • Private hiking trail on the property • Ideal basecamp for mountain biking, hiking, and outdoor adventures • Easy access to local trails, dining, and attractions

Guest favourite
Home in Gouldsboro
4.96 out of 5 average rating, 126 reviews

Poconos Lodge Retreat in Private Lake Community

The Lyman Lodge is a cozy retreat nestled in Big Bass Lake, a premier resort community in the Poconos. Enjoy all the region has to offer while relaxing with high-end comforts. Community amenities include lake access, indoor/outdoor pools, tennis, basketball, and pickleball courts, playgrounds, a splash pad, and fitness center. Lyman Lodge is also conveniently located near top Poconos attractions for year-round fun. Unwind and explore at the Lyman Lodge—your cozy Poconos hideaway!

Guest favourite
Home in Coolbaugh Township
4.96 out of 5 average rating, 25 reviews

The Scout House - Hot Tub/Sauna/Fire Pit/Projector

Escape to The Scout House. A modern A-frame nestled among the trees in the Poconos, with floor-to-ceiling windows that immerse you in nature. Thoughtfully designed for slow mornings and fireside nights, offering a perfect balance of privacy and comfort within a safe, quiet community. Perfect for couples, friends, or families — ski, hike, enjoy the lake, or just relax. Hot tub, sauna, fire pit, projector, and more — everything you need for a relaxing, fun stay.

Guest favourite
Chalet in Covington Township
4.97 out of 5 average rating, 59 reviews

Chalet with year round heated pool, sauna, jacuzzi

Secluded chalet tucked away in the woods of Moscow PA but central to all skiing and water park attractions. Three levels of the home provide ample space for big families to spread out with 4 bedrooms, 3 full bathrooms and 2 half bathrooms. Built in 2025 this is a brand new home ready to welcome your family for your mountain adventure. The pool is heated year-round with a full spa, sauna, and jacuzzi. Our backyard is fully fenced in and private.

Guest favourite
A spacious living area features a stone fireplace and large windows overlooking Lake Larsen. Comfortable seating is arranged on warm wooden floors, leading to an inviting outdoor deck with a dining table and umbrella. Natural light enhances the relaxing ambiance.
Home in Gouldsboro
4.87 out of 5 average rating, 293 reviews

Lake Front Retreat in the Poconos * King Bed*

Our single level lake home awaits your family's memories. Our 3 bedroom, 2 bathroom lake home accommodates up to 6 guests. Lake Larsen can be viewed from any point in our home. A King bed is provided in the master bedroom. Relax, Play, and Enjoy. Our home is located in the 5 * star community of Big Bass Lake. The town of Gouldsboro provides for a country setting, however it is very close to many of the Pocono's attractions.

Top guest favourite
A living area features two patterned sofas, a round coffee table, and a white rocking chair. Natural light filters through three large windows, illuminating the warm wooden floors. A standing lamp adds a cozy touch, while a decorative plant brings a hint of greenery.
Flat in Scranton
4.96 out of 5 average rating, 275 reviews

City Seclusion and Creative Retreat on the Brook.

total seclusion in East Mountain area of Scranton close to everything. Giant pine trees in a super quiet neighborhood offer a refreshing getaway or convenient stay for visiting relatives,going to music shows,concerts,mountain biking etc. Writers,artists and travelers will love this second floor walk up space. Note: There is no TV in the apartment. WiFi is available for streaming content on your devices.

Popular amenities for Madison holiday rentals