Chalet vacation rentals in Madison

Find and book unique chalets on Airbnb

Quick stats about chalet rentals in Madison

  • Total vacation rentals

    Explore 10 vacation rentals in Madison

  • Nightly prices starting at

    Madison vacation rentals start at $183 CAD per night before taxes and fees

  • Verified guest reviews

    Over 950 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Wifi availability

    10 of Madison vacation 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, 145 reviews

Lost Compass Cabin•Hike•Float•Unwind

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 outdoor space features a stone fire pit surrounded by several red chairs, providing a cozy setting for gatherings. A large wooden pergola offers shade to a dining area, which includes multiple tables and chairs, ideal for outdoor meals. The charming barn-style house is visible in the background.
Chalet in Intervale
4.89 out of 5 average rating, 177 reviews

Lodge Intervale - Firepit, Bar, Pool Table, Sauna.

An unforgettable experience, create new memories with your family in the heart of the White Mountains! This unique 1806 post and beam barn was moved from Ossipee and transformed into a beautiful mountain home. With an open concept living space, 5 tv's, foosball table, horseshoe pit and billiards lounge, you won't be bored! After a long day on the slopes, warm up in the sauna or enjoy the custom heated, stone shower. Grill burgers, make pizza or enjoy s'mores while stargazing by the fire. BYO Dog

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
4.88 out of 5 average rating, 130 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.

Top guest favourite
Chalet in Gilford
4.92 out of 5 average rating, 356 reviews

Amazing Lake/ Mountain View’s Gunstock Ski Chalet

Rustic mountaintop chalet nestled among pine trees with beautiful views of Gunstock Mountain Ski Area and Lake Winnipesaukee from the deck. Minutes to Gunstock for winter skiing/tubing and summer zip lining/ mountain coaster, and to Lake Winnipesaukee. Cozy glass-front wood stove for chilly nights, outdoor fire pit for marshmallows, a grill for summer cookouts. Includes board games, foosball, and air hockey for family fun. Quiet, peaceful, and surrounded by nature—perfect year-round getaway!

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
4.76 out of 5 average rating, 177 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, 344 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, 218 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.

Superhost
Chalet in Madison
4.81 out of 5 average rating, 147 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, 185 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
The inviting living area features a high vaulted ceiling with wooden beams. Cozy seating is arranged around a decorative area rug, and a stone fireplace adds warmth. Large windows provide natural light and views, while a dining space is adjacent to the kitchen with modern appliances.
Chalet in Conway
4.93 out of 5 average rating, 186 reviews

Luxurious Ski Retreat with Cozy Fireplace

Come stay in our cozy log cabin, Where the fire roars like a dragon. Just a hop, skip, and a jump away, From the slopes where you'll ski all day. Bring your furry friend, he'll love it too, We're dog-friendly, it's true, true, true. Luxury awaits in every room, From the plush beds to the bathroom. With nature all around, And peace and quiet to be found, This cabin is the perfect stay, For a fun and memorable holiday.

Guest favourite
Chalet in Madison
4.92 out of 5 average rating, 259 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.

Top guest favourite
The vintage ski chalet features a unique architectural style with a striking red exterior and stone accents. Expansive windows on the upper level provide views of the surrounding landscape. A wooden deck extends from the side, inviting outdoor relaxation in a serene mountain setting.
Chalet in Jackson
4.96 out of 5 average rating, 136 reviews

Breathtaking Mt Washington Views Jackson Chalet

Spectacular views of Mount Washington, Jackson Village, and the Presidential Range await you. From our home, you’ll enjoy one of the most breathtaking panoramas in all of the Mount Washington Valley. With bedrooms and bathrooms on all three floors, the layout is ideal for families and groups, offering plenty of space to spread out while still enjoying time together.

Popular amenities for Madison chalet rentals

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