Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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Guest favorite
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
4.83 out of 5 average rating, 18 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 favorite
A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.
Castle in East Stroudsburg
4.99 out of 5 average rating, 475 reviews

Pocono Castle: Dungeon Escape Room & Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Top guest favorite
A two-story yellow farmhouse is framed by lush greenery, with a stone walkway leading to the front entrance. The home features large windows and a welcoming porch with white railings. Nearby, a greenhouse is visible in the background.
Home in The Hideout
4.93 out of 5 average rating, 131 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.

Superhost
The dining area features a large wooden table surrounded by black chairs, designed to accommodate a group. Large windows provide a broad view of the wooded landscape, allowing natural light to fill the space. The ceiling is painted in a calming green hue, enhancing the overall ambiance.
Home in Mountainhome
4.89 out of 5 average rating, 106 reviews

Rustic Luxury Retreat | Hot Tub • Creekside Views

• 13 beds • 8 elegant bedrooms • 4 baths incl. 2 en-suites • Hot tub, fire pit, grill, and chic outdoor lounge areas • 8 secluded wooded acres with babbling creeks and serene forest views • Coveted location moments from premier attractions Enter a realm of elevated rustic elegance at this breathtaking 8-bedroom, 4-bath historic farmhouse estate , impeccably envisioned by architect Elisa Felisatti and artfully restored by master artisan Matteo DeLuca. A premier retreat for all seasons.

Superhost
An aerial view captures the Villa surrounded by lush greenery, showcasing a spacious outdoor deck leading to a sparkling pool. A pathway meanders through the property, while the inviting architecture blends with the natural landscape.
Home in Stroudsburg
4.86 out of 5 average rating, 100 reviews

!Poconos Hidden Villa de’Casablanca Pool+Spa Creek

Welcome to the Hidden Villa de’ Casablanca Pool + Spa Oasis!! The Villa has a style of its own!! With Its ambient open concept, and an abundance of natural light coming through the floor-to-ceiling windows, 3 acres of exciting activities and amenities all at your disposal! The 5,000 sq/ft Villa includes the pool, outdoor deck space for guests, hot tub spa and movie theater to create a Spectacular stay and yet very convenient location in the heart of the city of Poconos!!!

Guest favorite
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
4.96 out of 5 average rating, 113 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.

Guest favorite
Home in Coolbaugh Township
4.94 out of 5 average rating, 36 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 favorite
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, 310 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 favorite
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, 302 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 favorite
A cozy living area is highlighted by a light-colored, spacious couch adorned with patterned throw pillows. Two lamps provide soft lighting on either side, while sunlight fills the room through large windows, complemented by decorative artwork on the wall.
Apartment in Scranton
4.97 out of 5 average rating, 125 reviews

Lovely 4 bedroom rental with spacious master suite

Come stay at this unique and family-friendly apartment. 4,100 sq ft apartment located on the second floor of a historic mansion built in 1892. There is plenty of space for you to spread out and unwind. Beautiful bedrooms with 3.5 bathrooms that include a spacious master suite with tiled walk in shower and private balcony. Additional covered porch and large swing off of bright, sun light dining room to relax and enjoy the outdoors.

Guest favorite
An inviting backyard pool area features a curved, in-ground pool surrounded by smooth concrete decking. Lounge chairs are arranged on one side, with a shaded seating area nearby. The space is enhanced by a backdrop of lush greenery, creating a peaceful outdoor retreat.
Home in Long Pond
4.98 out of 5 average rating, 157 reviews

The Running Eagle. Pool, hot tub, and a game room.

***PRIVATE OUTDOOR POOL is open from Memorial Day Weekend through the end of September. Depends on the weather. Please check on exact dates. *** Running Eagle Modern Ranch located in The Estates @ Emerald Lakes! Yet another, designed with detail, equipped with all, and fully renovated SsMook home in Poconos. Relax in the Gameroom, a large home with a HOT TUB and in-ground pool. Pet fee is $50 per pet per stay.

Top guest favorite
Home in Gouldsboro
4.97 out of 5 average rating, 108 reviews

Lakeside Luxe: Lake Views, Theatre, Guest Favorite

Enjoy a summer lakeside escape at Lakeside Luxe in Big Bass Lake, featuring 4 bedrooms, 2.5 baths, peaceful water views, central AC, an 86” theatre room, arcade/game room, and cozy sunroom with swing and coffee bar. Spend your days at the community lakes, beaches, outdoor pool, splash pad, boat rentals, or trails, then grill, relax by the firepit, or unwind by the waterfall views.

Popular amenities for Madison vacation rentals