Holiday rentals in Madison

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Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 155 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!

Guest favourite
Tiny home in Gouldsboro
4.88 out of 5 average rating, 179 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, 122 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.

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!

Top guest favourite
A modern living space features a stone fireplace centered on a wall with a large mounted television. Two windows invite natural light and views of the wooded outdoors. Comfortable seating is arranged around a circular coffee table, complemented by a textured area rug.
Chalet in Pocono Lake
5 out of 5 average rating, 138 reviews

Chalet Retreat with HotTub, Fire Pit and EVCharger

Escape to Firefly Chalet, a modern and elegant private retreat nestled on a stunning 1-acre wooded property in Pennsylvania’s Pocono Mountains. Whether you’re planning a romantic weekend, family reunion, or extended stay, this tranquil chalet delivers the perfect year-round escape—unplug, recharge, and soak in nature right outside your door. This chalet is more than a stay—it’s your personal sanctuary in the Poconos. Book now and create unforgettable memories surrounded by nature.

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 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.

Top guest favourite
A cozy outdoor fire pit area is surrounded by six red Adirondack chairs, providing a welcoming setting for gatherings. Soft string lights illuminate the space, while the cabin's wooden structure stands in the background, nestled among trees in a tranquil environment.
Cabin in The Hideout
4.99 out of 5 average rating, 106 reviews

Cozy Poconos Cabin. Firepit, Beach & Lake Access

Welcome to Smugglers Nook:Your Perfect Pocono Escape! Escape to the beauty of the Pocono Mountains at Smugglers Nook, your cozy home-away-from-home nestled within the serene Hideout community. This charming 1,400 sqft cabin is designed for both relaxation and adventure, offering everything you need for a memorable getaway. Whether you’re here to unwind or explore, Smugglers Nook is the perfect choice.

Top guest favourite
A well-equipped kitchen features modern appliances, including a washer and dryer. Natural light filters through the window above the sink, illuminating the light-colored cabinetry and dark countertops. Shelves display dishware, while a decorative wall piece adds subtle charm.
Flat in Scranton
4.92 out of 5 average rating, 226 reviews

Beautiful Green Ridge Apartment in Scranton

Beautiful two-bedroom, third-floor apartment in Green Ridge. Walk to the area's best local coffee shop, yoga studio, or pizza place. A great place to relax and unwind with Wifi & local cable. Total renovation completed with all new flooring, painting, and furnishings. I have lived in NEPA my whole life and am excited to host a place for guests to stay and see Scranton and the surrounding areas.

Popular amenities for Madison holiday rentals