
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.

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!

White Mtns Waterfront Chalet w/ Private Beach
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!

Mountain View Chalet
Welcome to our Mountain View Chalet! With a gorgeous mountain vista this home is centrally located to area attractions! Mountain View Grand Resort is just down the road. Bretton Woods & Cannon are a short drive. Hiking trails, lakes, ski, & snowmobile trails all close by! Close to Littleton, Bethlehem, & Lancaster! Enjoy the landscaped back yard w/ fire pit & screened in patio. Hang inside & enjoy the view from the sunroom, or snuggle up on the couch in the cozy living room with wood stove.

Mountain Escape: Ski, Fireplace, Outdoor theater
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!

Cozy 4 Bedroom Chalet in the White Mountain Valley
Welcome to Mountain Escape, our completely renovated, cozy chalet in the White Mountain valley. This chalet is perfect home base to relax or discover all that the White Mountain region has to offer. Our house is located close to many great attractions: 2 minutes to Storyland, minutes to several ski mountains- Attitash (8 mins), Black Mountain (8 mins), Cranmore (13 mins), Wildcat (16 mins), Mount Washington Auto Road (29 mins), Diana’s Bath (12 mins), Echo lake (13 mins) and so on.

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.

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.

Mountain-view ski chalet w/ hot tub
Escape to 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 summer adventures in the mountains year-round.

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 Madison chalet rentals
Family-friendly chalet rentals

Cozy den- best winter getaway w hot tub/fireplace

Cozy Cabin| Dog Friendly |Fire Pit| EV charger

The Gem of Linderhof

Rustic 3 Bedroom Chalet in Eidelweiss!

Mountain Chalet near a Lake

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

Mt. Lakes Chalet

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

Peaceful Chalet in the White Mountain, Sleeps 15

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

Idyllic Mountain and Lake Getaway

5BR/2BA-Conway Chalet| Grill| Game Rm| | Fire pit

Cozy Chalet with Stunning Mountain Views

Mt. Wash views 3 floors bed/bath on each floor

East Branch Chalet (7 min to N Conway)

Spectacular Ski In Hideaway: Hot Tub - Views - BBQ
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.

Rustic Lakefront Cottage
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ903 | ﺩ.ﺇ746 | ﺩ.ﺇ712 | ﺩ.ﺇ595 | ﺩ.ﺇ918 | ﺩ.ﺇ830 | ﺩ.ﺇ1,098 | ﺩ.ﺇ1,135 | ﺩ.ﺇ1,025 | ﺩ.ﺇ951 | ﺩ.ﺇ881 | ﺩ.ﺇ914 |
| Avg. temp | -15°C | -14°C | -11°C | -5°C | 2°C | 8°C | 10°C | 9°C | 6°C | 0°C | -6°C | -11°C |
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.ﺇ477 per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

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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- Sebago Lake
- Squam Lake
- Story Land
- Scarborough Beach
- Sunday River Resort
- Weirs Beach
- Attitash Mountain Resort
- Loon Mountain Resort
- Mount Washington Cog Railway
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Dunegrass Golf Club
- Omni Mount Washington Resort
- Funtown Splashtown USA
- Willard Beach
- Cannon Mountain Ski Resort
- Tenney Mountain Resort
- Parsons Beach
- White Lake State Park
- Ferry Beach
- Cliff House Beach
- King Pine Ski Area
- Laudholm Beach