Chalet holiday rentals in Madison

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

Top Guest favourite

Guest favourite

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

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.

Comfortable chalet in Tamworth, walk to lake

Relax and unwind with the whole family and your pups at this chalet with a two-story great room with open kitchen, dining and living. On your 10 min walk (or 2 min drive) to the community beach you will pass a playground and basketball court. After you pass through the pine tree path to the lake, you'll find an expansive sandy beach perfect for swimming, jumping off the dock, fishing and paddle boarding or kayaking. Lounging at the house is lovely on the front porch or in the private backyard.

Top Guest favourite

Guest favourite

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!

Top Guest favourite

Guest favourite

The Birch House | Outdoor Theater + Fire pit + Ski

🍂 Fall in the White Mountains 🍂 Enjoy crisp autumn days exploring the White Mountains and cozy evenings under the stars at our private outdoor theater, complete with projector, cozy seating, string lights, and blankets. Gather around the firepit, grab your favorite snacks, and enjoy a movie beneath the fall sky. By day explore trails across the street, relax at the private neighborhood river beach, or visit Jackson’s covered bridge & falls. StoryLand and North Conway are just minutes away!

Top Guest favourite

Guest favourite

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.

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Top Guest favourite

Guest favourite

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.

Top Guest favourite

Guest favourite

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.