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
5.0 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.

Top guest favourite
Home in Penn Estates
5.0 out of 5 average rating, 249 reviews

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

Top 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, 445 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!

Superhost
Tiny home in Gouldsboro
4.86 out of 5 average rating, 181 reviews

private hot tub wii outdoor movies lake access

*OLYMPIC SIZED POOL & AQUATIC CENTER OPENS JUNE 25!* This spacious Pocono tiny home is fully stocked for your next memorable family vacation or romantic couple’s getaway. Soak in your private hot tub, toast s’mores by the fire, cozy up for movie night with our new outdoor projector, or enjoy hours of gaming on the Nintendo Wii. Endless fun awaits you with access to 2 beaches, Aquatic center (seasonal) mini golf, tennis courts, & more. Just minutes from skiing, casinos, hiking and waterparks.

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, 57 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
5.0 out of 5 average rating, 5 reviews

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

Top guest favourite
An evening view of the home features warm light glowing from the windows. Outdoor seating is present on the deck, and a fire pit with chairs is situated nearby in the yard. A covered hot tub is visible, adding to the inviting atmosphere.
Home in Tobyhanna Township
4.96 out of 5 average rating, 138 reviews

NEW Lakefront Home with Hot Tub

Situated on the water's edge of Arrowhead Lake, this brand new, custom built home offers a unique, luxury getaway for those seeking a stay with all that lakefront living has to offer. Perfectly set up for a romantic getaway for two, The Lakehouse on Arrowhead was created to provide a space for couples to rest and reconnect while enjoying gorgeous lake views from both inside and out. The spacious deck is just steps from your own private dock which allows you to kayak at your leisure.

Superhost
Home in Tobyhanna Township
New place to stay

Herons Rest Lakefront: Sand Beach, Kayaks, Hot Tub

Set directly on the water, Heron's Rest is a lakefront retreat designed for group stays. Enjoy mornings on the dock, afternoons kayaking, and evenings in the hot tub or around the firepit. With multiple living spaces, a pool table game room, and room for up to 8 guests, it’s ideal for families and lake escapes. Spend your days swimming or exploring the lake, then return to grill, relax, and unwind indoors. (Professional photos are scheduled for early July and will be updated soon.)

Guest favourite
Home in Coolbaugh Township
4.96 out of 5 average rating, 27 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, 62 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, 295 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
Aerial view of a lakeside cabin surrounded by lush greenery and trees, with a river flowing nearby. The cabin's exterior features a sloped roof and a spacious yard, providing a serene setting amidst nature.
Cabin in Greentown
4.95 out of 5 average rating, 43 reviews

Lazy River Cabin: Lakefront Stay

Welcome to the Lazy River Cabin Lakefront Stay on Lake Wallenpaupack! This chic 3-bedroom, 3-bathroom retreat combines modern amenities with tranquil Poconos scenery. Expertly designed, it serves as your ideal home away from home, perfect for lakeside relaxation and easy access to local attractions. Unwind, relax, and make lasting memories with loved ones at this serene getaway, featuring a private dock and spacious backyard.

Popular amenities for Madison holiday rentals