
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•White Mountain Getaway
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!

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!

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.

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!

N Conway 10 min/Waterfront /Private Beach/fire pit
Peace comes dropping slow at this pond side chalet in Eidelweiss Village, an alpine oasis only 15 mins from North Conway. Here, on a private sandy beach, you can swim in calm waters; take a canoe or a kayak out for a leisurely row; toast marshmallows at a private fire pit and gaze up at a trillion stars in night skies unpolluted by urban glare. In the Winter months, you can ice skate on Little Pea Porridge Pond or go skiing at Pine King or Cranmore, or simply enjoy dinner with a view...

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.

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.

A-Frame near Lake and Attractions
Our 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/ bike week.

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.

Little Pine Lodge in the White Mountains
Mountain retreat says it all! Our A-frame home is a place where you can disconnect and is designed for the outdoor enthusiast in mind. Comfortable, casual, clean and inviting. Many nights have been spent outside enjoying time with friends and family by the fire pit and after a warm day a hot outdoor shower is heaven to come home to. Operator's Licence #063835
Popular amenities for Madison chalet rentals
Family-friendly chalet rentals

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

White Mountain Escape | Game Room + Mountain Views

Serene Forest Chalet - Beaches | Kayaks | Bikes

Chalet Cottage with Spectacular 7-mountain view

Large vacation home with a view

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

Gas fireplace + stargazing deck 4 mins from skiing

Mountain Lakes. Pet friendly. Entire Chalet.
Luxury chalet rentals

Lakes, Paddle boards, Beach - Sleeps 8 Bridgton

White Mountain Hideaway: Chic North Conway Chalet

Caldon Cabin - Waterville Estates Log Home Getaway

Ski & Lake Retreat w/ Epic Views

Chalet Near Downtown | Firepit + Porch | Pets

Modern Mountain Chalet Near Storyland & Summer Fun

Chalet with sunset mountain views

Luxury chalet near StoryLand w/fireplace-3 br;2+ba
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 € 94 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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- White Mountain National Forest
- Sebago Lake
- Story Land
- Squam Lake
- Weirs Beach
- Sunday River Resort
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Omni Mount Washington Resort
- King Pine Ski Area
- Gunstock Mountain Resort
- Cranmore Mountain Resort
- Waterville Valley Resort
- Conway Scenic Railroad
- Cannon Mountain Ski Resort
- Ragged Mountain Resort
- Diana's Baths
- Funtown Splashtown USA
- Pleasant Mountain Ski Area





