Chalet holiday rentals in Madison

Find and book unique chalets on Airbnb

Quick stats about chalet rentals in Madison

  • Total holiday rentals

    Explore 10 holiday rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at $141 SGD per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Madison holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Madison rentals

  • 4.9 Average rating

    Madison stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated chalet rentals in Madison

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

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Top guest favourite
Chalet in Conway
4.94 out of 5 average rating, 138 reviews

Lost Compass Cabin•White Mountain Escape

Escape to the White Mountains in this cozy, private Conway cabin-just minutes from North Conway shops, Cranmore, and the Kancamagus Highway. Perfect for families, couples, and small groups looking for a quiet retreat with easy access to skiing, hiking, and downtown fun. Seasonal Highlights ❄️ Winter ❄️ •Ski Cranmore•Attitash•Loon •Cross country skiing•Ice skating •Cozy nights by the fireplace ☀️Spring/Summer☀️ •Hike off the Kanc •Diana’s Baths •Kayaking•Swimming holes 🍁Fall🍁 •Leaf peeping

Guest favourite
An indoor fireplace stands against a light-colored brick wall, complemented by decorative pampas grass in a vase. A cozy seating area features plush cushions, while a spacious sleeping area is visible in the background with a king-size bed and ample natural light from large windows.
Chalet in Intervale
4.84 out of 5 average rating, 261 reviews

Cozy 1 Bed Chalet w/ King Bed & Indoor Fireplace

Cozy up at this unique and tranquil getaway cabin. Perfectly set up for 2 people, this charming A-frame is spacious, peaceful and well thought out. If its a romantic getaway you are looking for, look no further!! - with the king four-poster bed, the indoor fireplace & large, private back deck with grill you will have everything you need to enjoy & relax during your stay in the White Mountains. Close enough to everything to be convenient yet far enough away from it all for privacy and peace!

Superhost
A spacious chalet is nestled in a wooded setting, featuring a symmetrical facade with large windows that invite natural light. An expansive deck extends along one side, offering outdoor space. The exterior is clad in light-colored siding, surrounded by lush greenery.
Chalet in Tamworth
4.87 out of 5 average rating, 127 reviews

Rustic Mountainside Chalet

Located on a wooded mountainside in the White Mountains & the Lakes Region of NH, close to hiking, 5 minutes to the rivers and 15 minutes to Lake Chocorua and Lake Ossipee for swimming/kayaking/tubing or just relax and enjoy the views of the mountains. Peaceful Chalet with one bedroom with one bunk bed unit with queen mattresses, and a large master bedroom loft with Cali King, kitchen, and 2 x bathrooms, a deep jetted tub. The basement is converted into an in-law’s suite where my parents live.

Guest favourite
The exterior of the chalet is framed by lush greenery, showcasing a charming wooden structure with a red front door. A spacious lawn filled with blooming flowers adds a vibrant touch, while tall trees provide a natural backdrop against a bright blue sky dotted with clouds.
Chalet in Franconia
4.92 out of 5 average rating, 106 reviews

Franconia Getaway Chalet

The Getaway Chalet is a 3 bedroom, 1.5 bathroom, family-friendly house close to Cannon Mountain in Franconia. The perfect destination for all seasons, it's nestled in the mountains, a 4-minute drive from the ski resort. Cross-country trails are adjacent. Easy access to the state's most beautiful hiking and mountain biking, as well as swimming at Echo Lake and nearby golf. Three levels including a downstairs playroom, large yard, and front porch with the music of a babbling brook down the hill.

Guest favourite
The A-Frame cabin features a striking black exterior accentuated by bright yellow trim. A large umbrella shades a wooden deck with seating, inviting relaxation. Surrounding trees create a serene atmosphere, enhancing the cabin's secluded charm within the natural landscape.
Chalet in Denmark
4.89 out of 5 average rating, 152 reviews

Maine A-Frame with Hot Tub, Game Room, Lake Access

Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Enjoy our hot tub and game room Come experience our slice of heaven for yourself, you won’t regret it!

Guest favourite
An open-concept living area features a wooden dining table set with placemats and a centerpiece. The kitchen showcases dark cabinetry and modern appliances, while a cozy seating area includes a recliner and a large sofa. Light floods the space through expansive windows and skylights.
Chalet in Bartlett
4.75 out of 5 average rating, 171 reviews

Quaint Mountain Chalet: Min to No. Conway + Hiking

Spectacular Location Situated just a short walk from the crystal-clear waters of the Saco River or hike up beautiful Mount Stanton, our chalet offers endless outdoor adventures- at your doorstep. Close to Everything Our prime location is a hub for all the area's attractions. Storyland, historic Jackson, Attitash, and multiple ski resorts are just a stone's throw away. Whether you're a thrill-seeker or looking for family-friendly fun, you're in the perfect spot to make the most of your stay.

Guest favourite
A covered porch offers a spacious outdoor setting with wooden rocking chairs and a bench. Scenic views of fall foliage and rolling mountains are visible in the background, providing a serene environment for relaxation.
Chalet in Franconia
4.95 out of 5 average rating, 340 reviews

Bear Ridge Lodge

Newly built, chalet-style log home featured in both Cabin Living and Log Cabin Homes Magazines. Sweeping mountain and sunset views. Modern, Scandinavian decor. Generous front deck and covered porch for sunbathing, stargazing and outdoor dining in the summer and fall. Soaring stone fireplace makes for a warm, fully-appointed ski lodge in the winter months. 5 minutes from Cannon and 20 minutes from both Loon and Bretton Woods. Miles of National Forest trails out the back door.

Top guest favourite
A bright living area features a wood-burning stove and large windows allowing natural light. Two modern armchairs surround a natural wood coffee table, placed atop a cowhide rug. A decorative basket and firewood are visible on one side, enhancing the warm ambiance.
Chalet in Conway
4.96 out of 5 average rating, 212 reviews

HAPPY TREES: swanky chalet near Conway Lake & Saco

Happy Trees is a vintage chalet that has been thoughtfully renovated and styled. Our place is bright, airy, and open. It's the perfect home base for whatever you may want to do whether it's skiing, swimming, hiking, or simply relaxing and lounging around. Our place is a short walk to Conway Lake and a short drive from the Saco River. Conveniently located minutes from North Conway village. Follow us on IG (@happytrees_cabin) for additional content & information.

Guest favourite
Chalet in Madison
4.81 out of 5 average rating, 141 reviews

Pond-Side Chalet • Private Beach • Canoe & Kayak

"So close to the water's edge you could practically fish from the deck." That's what guests say about Idylweiss Chalet, our pond-side chalet in Eidelweiss Village, 15 minutes from North Conway. Mornings on the deck with the loons calling across Little Pea Porridge Pond. Afternoons on the private sandy beach with the canoe and kayak. Sleeps seven across three bedrooms and two full bathrooms. A short drive to Storyland, ski resorts, and the Kancamagus Highway.

Top guest favourite
Chalet in Intervale
5 out of 5 average rating, 181 reviews

Family-friendly w/ mountain views & hot tub!

Relax at Valley Vista Lodge, our family-friendly White Mountains chalet with panoramic mountain views and 3,000+ sq. ft. of space. Relax in the private, covered hot tub, cozy up by the fireplace, or spread out across five bedrooms. Perfect ski rental near Attitash, Cranmore, and Wildcat, just 3 minutes from Story Land and 10 minutes to North Conway shopping. Ideal for multi-family getaways, ski weekends, and adventures in the mountains year-round.

Guest favourite
Chalet in Madison
4.92 out of 5 average rating, 256 reviews

Chalet/close to N Conway, far enough away from all

Please read our Coronavirus cleaning update. Quaint and cozy chalet located about 5 minutes from Conway and the hub of the White Mountains. As you pull into our neighborhood you notice several chalets on a paved road, winding up and over hills. Pull into our large carport to find our two level chalet that you have rented. The sounds of the babbling brook greet you as you exit your car with the inviting seating on both decks.

Guest favourite
Chalet in Gilford
4.92 out of 5 average rating, 352 reviews

Amazing Lake & Mountain views Gunstock Ski Chalet

Rustic Mountaintop Chalet nestled among the pine trees. Beautiful views of Gunstock Mountain Ski Area and of Lake Winnipesaukee from the large deck. Just minutes to the ski slopes in the Winter or to the lake in the Summer. A glass front wood stove for chilly nights, and an outdoor fire pit for roasting marshmallows. Board games, a foosball table, and an air hockey table for family fun. Quiet & peaceful!

Popular amenities for chalet rentals in Madison

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