
Chalet vacation rentals in Madison
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Top-rated chalet rentals in Madison
Guests agree: these chalets are highly rated for location, cleanliness, and more.

Lost Compass Cabin•Relax• Explore
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!

Waterfront w/ Private Beach, Fire Pit & Canoe
This charming chalet is nestled on the edge of Little Pea Porridge Pond in the enchanting village of Eidelweiss, an alpine oasis just a short drive from Mt Washington Valley. Enjoy campfires on a private sandy beach; Fishing, swimming and boating in the warmer months; Snowmobiling, skiing and ice-skating in the Winter season. Nearby attractions incl. King Pine, Cranmore and Attitash Ski Resorts; N Conway Village; Kancamaugus Highway, Hiking Trials, Waterfalls, shopping and gourmet restaurants.

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.

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.

Spring Escape: Cozy Home & Outdoor Movie Theater
Escape to North Conway this spring, where mountain air is crisp, waterfalls are flowing, and blooming trails await. Our cozy retreat is close to downtown shops, cafés, and scenic hikes. Enjoy peaceful mornings sipping coffee while bird watching, sunny afternoons exploring trails or waterfalls, and relaxing evenings stargazing or enjoy the outdoor movie theater. Perfect for couples, families, or a weekend away with friends—spring is the hidden gem season in the White Mountains 🌿

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.

Chalet/close to N. Conway, multiple skiing resorts
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!

A-Frame in Gilford
Our cozy A-Frame home is just minutes from Gunstock Mountain Resort and the Gilford town beach at Lake Winnipesaukee. Three bedrooms can accommodate up to 6 guests, with 2 queens, and 1 full, and 1.5 bathrooms. Outdoor area includes a hot tub, fire pit, brand new large deck with dining table/seating, and a gas grill. 1 mile from Bank NH Pavillion and 5 miles from Weirs Beach.
Popular amenities for Madison chalet rentals
Family-friendly chalet rentals

Mountainside Chalet at Mittersill

Family & Pet| Game Room| EV Charger |Cozy| Firepit

White Mountain Escape | Game Room + Mountain Views

Serene Forest Chalet - Beaches | Kayaks | Bikes

Chalet Near Downtown | Firepit + Porch | Pets

Cozy Mountain Chalet+ Hot Tub+ Firepit+ Game Room

Chalet Cottage with Spectacular 7-mountain view

Cozy cabin in the woods- great location
Luxury chalet rentals

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

Hemlock House

Idyllic Mountain and Lake Getaway

White Mountain Hideaway: Chic North Conway Chalet

Ski & Lake Retreat w/ Epic Views

Spacious Mountain Chalet: Game Room & Pet-Friendly

Modern Mountain Chalet Near Skiing & Attractions

Crystal Lake Chalet | Hot Tub, Sauna, Lake Access
Lakefront chalet rentals

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
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 G$23,010 GYD per night before taxes and fees

Verified guest reviews
Over 940 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!
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- Chalet rentals Carroll County
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- Chalet rentals United States
- White Mountain National Forest
- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- Tenney Mountain Resort
- East End Beach
- King Pine Ski Area
- Cranmore Mountain Resort
- Franconia Notch State Park
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Cannon Mountain Ski Resort
- Diana's Baths
- Ragged Mountain Resort
- Waterville Valley Resort
- Funtown Splashtown USA
- Pleasant Mountain Ski Area
- Conway Scenic Railroad




