
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 ﺩ.ﺇ 477 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 & kid-friendly amenities

Wi-Fi availability
10 of Madison vacation rentals include wi-fi 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.

Lost Compass Cabin•Firepit•River• Mountains
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

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

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.

One-of-a-kind log home
A truly unique mountain getaway! Close to all that the White Mountains and North Conway have to offer,in a private and idyllic setting with mountain views. While the main level tends to offer a peaceful retreat, the ground level is the place to entertain. With the hot tub and outdoor firepit overlooking the mountains, no need to go out. A ski enthusiast’s dream location, minutes away from Cranmore, Attitash Bear Peak, and the MWV Ski Touring Center! Delicious dining & plenty of shopping nearby!

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!

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!

Summer Oasis: Fire Pit & Outdoor Movie Nights
Enjoy magical nights under the stars at our outdoor theater—complete with projector, cozy seats, string lights, and blankets. Our private backyard cinema offers a one-of-a-kind experience, just add your favorite snacks! By day, explore the White Mountains with trails across the street, a private river beach in the neighborhood, or visit Jackson’s covered bridge & falls. StoryLand + North Conway are just minutes away. You're at the doorstep to everything the White Mountains have to offer!

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.

Family Ski Chalet | Dogs | Hot Tub | Fire Pit
Welcome to your mountain getaway, nestled near the heart of one of the valleys most sought-after ski resorts - Attitash Mtn. This charming 2-bedroom chalet is a haven for families or responsible groups of friends seeking a perfect getaway just minutes from the slopes. Enjoy an open, covered three-season porch out front and an open deck out back with grill, fire pit and outdoor seating to suit any season. Bring the dogs and hit the trails in this year round retreat!

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.

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.

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.
Popular amenities for Madison chalet rentals
Family-friendly chalet rentals

Relax Under the Stars | Hot Tub • Fire Pit • Deck

Private home with garage - ideal N Conway getaway!

Blueberry Hill

Cozy Chalet on the River

Luxury chalet near StoryLand w/fireplace-3 br;2+ba

Epic White Mountain Chalet Getaway in Jackson

Dog and Family Friendly in Heart of Mount Washingt

Good Friday Chalet | Walk to Village + Cranmore Mt
Luxury chalet rentals

Family-friendly w/ mountain views & hot tub!

Breathtaking Mt Washington Views Jackson Chalet

East Branch Chalet (7 min to N Conway)

Pine Brook Lodge, 9 br, 5 ba, game room, fireplace

The Moose Chalet- Walk to Diana's Baths!

Hot Tub, 5 Beaches Nearby, 4BR, Dog & Kid Friendly

Chalet Near Downtown | Firepit + Porch | Pets

Serene Forest Chalet - Beaches | Kayaks | Bikes
Lakefront chalet rentals

The Chalet~ 4 bed Lakefront Family Vacation

Mountain cabin with views, privacy, and more.

Crystal Lake Chalet | Hot Tub, Sauna, Lake Access

Waterfront/Private Dock/HotTub/Pool & Amenities

Pondside Getaway - Fishing, Canoeing, & Skiing

Charming & Cozy 3 Bedroom Chalet

Rustic Lakefront Cottage
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- Sebago Lake
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Willard Beach
- Mount Washington Cog Railway
- Scarborough Beach
- East End Beach
- Santa's Village
- Tenney Mountain Resort
- Cranmore Mountain Resort
- Franconia Notch State Park
- Hills Beach
- Sunday River Resort
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Pleasant Mountain Ski Area
- Waterville Valley Resort
- Echo Lake State Park
- Diana's Baths
- Crawford Notch State Park
- Attitash Mountain Resort





