
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.

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

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!

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.

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.

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!

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.

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.

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.

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.

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.

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
Family-friendly chalet rentals

Family Friendly, Game Room, EV Charger, Fire-pit

Serene Forest Chalet - Beaches | Kayaks | Bikes

Chalet Near Downtown | Firepit + Porch | Pets

Chalet Cottage with Spectacular 7-mountain view

Mountain View Chalet

Timberhaus | Alpine Chalet | Fire Pit • Story Land

Modern Chalet: Pet-Friendly 3BD/2Bath | Kids Bunk

Secluded home-Upper Unit, Hot Tub & Pond Access
Luxury chalet rentals

Lakes, Paddle boards, Beach - Sleeps 8 Bridgton

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

6 BR | EV Charger | No Pet Fee | Pool Table

Summer Oasis: Fire Pit & Outdoor Movie Nights

White Mountain Hideaway: Chic North Conway Chalet

Caldon Cabin - Waterville Estates Log Home Getaway

Ski & Lake Retreat w/ Epic Views

Cozy Mountain Chalet+ Hot Tub+ Firepit+ Game Room
Lakefront chalet rentals

On Lake Christopher, Close to Sunday River

Charming & Cozy 3 Bedroom Chalet

Pondside Getaway - Fishing, Canoeing, & Skiing

Mountain cabin with views, privacy, and more.

The Chalet~ 4 bed Lakefront Family Vacation

Waterfront/Private Dock/HotTub/Pool & Amenities
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Island of Montreal Holiday rentals
- Cabin rentals Madison
- Pet-friendly rentals Madison
- Rentals with outdoor seating Madison
- Rentals with a washing machine and dryer Madison
- Waterfront rentals Madison
- Rentals with a firepit Madison
- House rentals Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with a hot tub Madison
- Rentals with a patio Madison
- Rentals with lake access Madison
- Rentals with a kayak Madison
- Rentals with a fireplace Madison
- Chalet rentals Carroll County
- Chalet rentals New Hampshire
- Chalet rentals United States
- White Mountain National Forest
- Sebago Lake
- Story Land
- Squam Lake
- Weirs Beach
- Sunday River Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- Loon Mountain Resort
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Omni Mount Washington Resort
- King Pine Ski Area
- Cranmore Mountain Resort
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Conway Scenic Railroad
- Waterville Valley Resort
- Cannon Mountain Ski Resort
- Diana's Baths
- Pleasant Mountain Ski Area
- Hills Beach





