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.

Guest favourite
Home in Newfoundland
4.93 out of 5 average rating, 55 reviews

Renovated Luxury Home in Poconos

This newly renovated home located in the heart of Pocono Mountains is overlooking a peaceful pond, offers luxury amenities like a hot tub, sauna, and game room, plus a children's room designed with fun in mind. The modern, fully equipped kitchen features a coffee bar with an expresso machine! Perfect for families, this stylish home offers both relaxation and fun in a private, serene setting. Minutes from state parks and other mountain adventures. More guests can be accommodated upon request.

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
An exterior view of The Cedar House reveals a charming wooden facade complemented by a stone pathway. Lush green grass surrounds the entrance, where colorful flower pots enhance the inviting appeal. Large windows allow natural light to fill the inviting spaces inside.
Home in Spring Brook Township
4.96 out of 5 average rating, 111 reviews

THE CEDAR HOUSE

Escape to the foothills of beautiful Pocono Mountains, enjoy the beauty of nature surrounding The Cedar House. Bring your family, friend and pets. Create beautiful memories from PA. Enjoy the five and a half acres of land, and wild animals passing by . At night enjoy the outdoor fire pit or warm up by the woodstove. Relax under the shade of trees, read a good book and admire lake view. The Cedar House has an unique interior, furnished with custom furniture.

Top guest favourite
An outdoor fire pit area is surrounded by gravel and lush green grass. Two wooden chairs are positioned on either side of the fire pit, with a red shed visible in the background next to the house, which is nestled among the trees.
Home in Greentown
5 out of 5 average rating, 20 reviews

Alice's House: Summer Fun for Friends and Family

Escape to The Great outdoors in Northeast Pennsylvania. Just a 2-hour drive from both New York City and Philadelphia. Welcome to Alice's house a fully furnished two bedroom one bath home nestled deep in the serene woods of northeast Pennsylvania Just minutes from Lake Wallenpaupack and Promised Land State Park. Enjoy endless outdoor adventures including biking,hiking, kayaking, boating, fishing and antiquing, or just relax with your friends or family.

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.

Popular amenities for Madison holiday rentals