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

A window offers a clear view of the lush greenery outside, showcasing a serene forest scene. A wooden table with a placemat is visible in the foreground, along with a red mug resting on it, inviting a cozy atmosphere.

Home in Lake Ariel

4.9 out of 5 average rating, 156 reviews

owl's nest rustic retreat

Relax in nature when you stay at this restful retreat situated on 2 quiet acres of calm wooded wonderland. The 2-bed, 1-bath cabin accommodates up to 6 guests. Spacious living room and ample kitchen space make sure that entertaining your group is a breeze. Outdoor deck with grill for BBQ nights. The covered front porch is ideal for watching the wildlife pass through the property. Cozy up next to the fire pit for s'more fun! Enjoy exploring all that the Poconos has to offer when you stay here!

Superhost

The exterior of the cabin is surrounded by a blanket of fresh snow. The wooden structure features a covered porch with a set of stairs leading to the entrance, while trees in the background appear dusted with white.

Cabin in Roaring Brook Township

4.91 out of 5 average rating, 33 reviews

Blue Shutters Cabin Retreat!

Nestled on 165 acres of private land, Blue Shutters Cabin Retreat offers an escape from the hustle and bustle of every day life. Whether you're seeking adventure or serenity, Blue Shutters Cabin has it all. Some of Blue Shutters highlighting features: Dual Purpose Dinette Table (converts to Poker Table), 10 Speaker Surround Sound + Bluetooth, Billiards Room (9ft table), Sauna+ Steam Room, Gas Grill, Fire Pit, Professional Outdoor Ping Pong Table, Bocce, Horseshoes, Chess, Checkers and more!

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.

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, 125 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

The log cabin is illuminated at night, showcasing its rustic design. A porch with steps leads to the front door, framed by greenery and flower beds. A picnic pavilion is visible nearby, and a parked car is situated on the gravel driveway.

Cabin in Greentown

4.97 out of 5 average rating, 73 reviews

Romantic cabin /hot tub/king bed/coffee bar/cable!

Hot tub, Outdoor theater, Firepit, Coffee bar, Picnic pavilian with BBQ, Cornhole, GIANT Jenga, board games, Smart TVs, premium cable, NFL RedZone, fully stocked kitchen, and Minutes from three local marinas! This brand new log cabin offers peek-a-boo lake views, rustic design & modern comforts all within a picturesque setting for a peaceful getaway. With all the amenities you could possibly desire for a relaxing vacation. Make your getaway unforgettable with us!

Top guest favourite

An elegant bathroom features a freestanding soaker tub positioned by a large triangular window. Natural light floods the space, showcasing views of surrounding trees. A small green stool complements the decorative patterned tile floor, while potted greenery adds a touch of nature.

Cabin in The Hideout

4.96 out of 5 average rating, 305 reviews

Condé Nast featured A-frame. Hot Tub. Lake. Pools

Sink into the hot tub and let the Poconos do the rest. This Condé Nast-featured mid-century A-frame is nestled among the trees, just minutes from the lake — a beautifully curated escape two hours from NYC with everything you need to completely unwind. Soaker tub with a tree-top view, chef’s kitchen, fire pit, community pools, and a bathroom so good it’s been featured in Condé Nast, Houzz and West Elm. This is the one you’ve been saving on Pinterest

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

Home in Barrett Township

5 out of 5 average rating, 6 reviews

Boutique Farm Stay | 30 Acres & Baby Goats

Escape to a beautifully renovated modern farmhouse set on 30 private acres in the Pocono Mountains. Delivering a boutique resort-quality experience, the home features designer interiors, luxury bedding, a fully equipped kitchen, and a stunning stone fireplace. Explore the seasonal creek, meet our friendly baby goats and rabbits, and enjoy the peaceful surroundings of the Ik & Lo Resort at Barn Swallow Stables, a boutique nature resort.

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.