Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Guest favourite
A charming cottage exterior is framed by lush greenery, showcasing a blend of stone and wooden siding. A wooden ramp leads to the entrance, providing accessibility. Tall trees surround the property, enhancing the natural setting and creating a peaceful atmosphere.
Cottage in Barrett Township
4.93 out of 5 average rating, 231 reviews

Peaceful & Private * Hot Tub, Fire Pit, Hammock

Fun in the Pocono Mountains. Property is Beautiful and Cozy with a Year round Hot Tub ready for you to climb in and RELAX! Fully stocked kitchen, clean linens supplied for the comfortable queen sized beds. Hiking, ATV’s, horseback riding, Skytop adventure center is 3 minutes to Zip Line, Treetop Climb, Paintball, Arrow Tag. Excellent food & drinks at several very local restaurants. Also close to Casino, Camelback & Kalahari. Discounts for multi night stays Fast Wi-Fi and “convertible” workspace

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.

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, 154 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, 32 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
Tiny home in Gouldsboro
4.88 out of 5 average rating, 178 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
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, 121 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, 53 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.

Top guest favourite
Home in Gouldsboro
4.96 out of 5 average rating, 124 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
A cozy living area features a large sectional sofa adorned with neutral-toned pillows and a soft throw. A wooden coffee table sits in the center, displaying decorative items. Natural light filters through two large windows, enhancing the warmth of the space.
Flat in Scranton
4.92 out of 5 average rating, 66 reviews

Luxury Apartment in Scranton's Hill Section

Luxury apartment located in a historic, beautiful, 14,000 sq. ft mansion in the heart of the Hill section of Scranton. This home was originally built in 1892 for a coal baron and has a rich history. The apartment is truly one of a kind with generous rooms, 12 foot high ceilings, custom kitchen, along with a peaceful and private stone patio located at the back of the apartment. The stone patio is part of the professionally landscaped backyard gardens that you are welcome to enjoy!

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, 303 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.

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, 274 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