Holiday houses in Madison

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Top-rated holiday rentals in Madison

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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
4.82 out of 5 average rating, 17 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.

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Top Guest favourite
Home in Penn Estates
5 out of 5 average rating, 258 reviews

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

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Guest favourite
Tiny home in Gouldsboro
4.87 out of 5 average rating, 187 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.

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Guest favourite
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, 128 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.

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Guest favourite
Home in Lake Ariel
5 out of 5 average rating, 6 reviews

Lakefront, Dock, Boats, Hot Tub, Game Room

🌲 Welcome to your private Lake Henry retreat, The Stillwater House, where stunning waterfront views, modern renovations, & endless entertainment come together for the perfect getaway. Whether you're paddling across the lake, soaking in the brand-new hot tub, or enjoying movie night with your crew, this home was designed for making memories. 🌊 Lakefront + Private Dock 🛶 Kayaks, Paddle Board & Row Boat 🔥 7-Person Hot Tub 🎬 Movie Room + Game Room 🪵 Fire Pit & Hammock 🔥 Fireplace

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Guest favourite
The cabin is set amidst autumn foliage, surrounded by trees displaying vibrant fall colors. A wooden deck with steps leads to the entrance, while a fire pit is framed by four rustic chairs on a gravel surface, inviting outdoor gatherings.
Cabin in Pocono Pines
4.96 out of 5 average rating, 143 reviews

Family Friendly Cabin I Firepit+Hot Tub I Poconos

Enjoy this stylish Poconos cabin located a short distance from multiple lakes, skiing, and golf courses.. (please note Lake Naomi is PRIVATE and we dont have a membership) → Smart TV → Solid WiFi → Fully Equipped Kitchen → Hot Tub → Fire pit & Awesome Deck → 13 miles from Snow Ridge Village → 3 miles to Timber trails and Pinecrest Lake Gold Course → 10 mins to Kalahari Waterpark/waterfalls → 20 mins to Camelback Mountain Adventures STR Permit Number #020578 Minimum Age to Rent: 25

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Top Guest favourite
Home in Tobyhanna
4.98 out of 5 average rating, 119 reviews

Stylish Chalet Getaway in the Poconos

A magical 3-bedroom, 1-bathroom Pocono chalet bordering Tobyhanna State Park right in your backyard, with a treehouse feel, window-wrapped interiors, luxury touches, a private new 6–7-seater hot tub, fire pit, pergola BBQ lounge, and access to Lake Carobeth, pools, and more within a gated community. Your perfect mountain getaway starts here. Come hide away in the trees, soak under the stars, and experience a Pocono stay that feels equal parts fairytale, luxury, and romance.

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Guest favourite
Home in Coolbaugh Township
4.94 out of 5 average rating, 33 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.

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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, 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.

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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, 308 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

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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, 300 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.

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Top Guest favourite
Home in Gouldsboro
4.97 out of 5 average rating, 107 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.

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Popular amenities for Madison holiday rentals