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

Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!
Three Peaks Cabin is a one of a kind Beautiful Mountain Home located in tranquil Bryant Pond Maine. Home sits atop peak that has direct views of the White Mountains, Lake Christopher and more as well as a stone throw away from world class skiing at Sunday River & Mt Abram. You'll feel right at home when you walk through the doors of this Bryant Pond vacation rental. The 3-bedroom, 2 -bath chalet-style house features 1625 square feet of beautiful living space complete with tasteful decor, with three large Pella French doors pointing directly west with views of Mt. Abram and Mt. Washington. Overlooking the Lake Christopher and surrounded by trees at the end of a cul-de-sac, this home offers families and groups plenty of outdoor recreation opportunities from boating and watersports to hiking, biking, and skiing! 65" Flat-Screen TV equipped with Dish Network Satellite, w/ Netflix, Prime Video, Dish Multisport w/ NFL Red zone | Gourmet Kitchen | Floor-to-Ceiling Windows From outdoor sports to downtown Bethel's unique shops and restaurants, this upscale retreat is the perfect getaway spot for families and groups! Bedroom 1: Queen Bed | Bedroom 2 Two Twin Beds | Bedroom 3: Two Twin Beds. OUTDOOR LIVING: Full private yard, with beautiful manicured grass and flowers during summer and fall months. Brand new Weber Gas grill, well designed fire pit with new Adirondack chairs & lovely outdoor sitting area with tables and chairs to sit and enjoy the view of the white mountains. INDOOR LIVING: 2 flat-screen TVs w/ streaming capabilities, Floor to ceiling fireplace which accompanies a large sectional couch to cozy up on the cool Maine nights next to the fireplace. dining table which sit four. The beautiful Gourmet Kitchen comes with stainless steel commercial gas range, Large stainless steel Refrigerator stocked with fresh neighboring Poland Spring waters, Stainless steel Dishwasher as well as an island where two additional seats are available. The downstairs bathroom also comes with a jacuzzi bath tub ready to relax the night away after a long day of enjoying western Maine festivities. KITCHEN: Fully equipped, drip coffee maker, keurig coffee & latte maker, toaster, cooking utensils, cutlery, spices, stainless steel appliances, dishware & flatware, breakfast bar GENERAL: Free Wi-Fi, central heat, central a/c, ceiling fans, towels/linens, complimentary toiletries such as Shampoo, Conditioner, Body Wash, Lotion, Goat Milk Soaps etc. & washer/dryer FAQ: Pet fee (paid pre-trip), stairs required for access PARKING: Driveway (4 vehicles) Three Peaks Cabin is located at 110 Yawkey Way, Bryant Pond, Maine. The home is located on a private street maintained by our HOA association. There are 6 total houses which included "Three Peaks Cabin". The property is located all the way up a steep paved road, last house on the right at the end of the culdesac.

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.

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.

Mt. Wash views 3 floors bed/bath on each floor
Spectacular views of Mount Washington, the Jackson Village, and the Presidential Range. One of the best views in all of Mount Washington Valley. Our home is a vintage 1965 Ski Chalet, and this means it’s full of quirks and character and that’s why we love it so much. It's clean and tidy and we are constantly working on maintenance and renovation projects. So if you are more comfortable in a sleek modern place, we gently suggest our place might not be the best fit for your holiday.

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.

5 Mins to Downtown NoCo, Storyland, & Echo Lake!
PRIME location! Private, secluded four-season chalet in North Conway, NH less than 1 mile from Cranmore Mountain, and <5 minute drive to downtown! NOCO offers shopping and a variety of restaurants, all while being minutes from Story Land, Echo Lake, Diana’s Baths, hiking, golfing and the NEW Mountain Adventure Park! This park offers zip lining, summer tubing, mountain coaster, inflatable obstacle course and so much more! Come enjoy your summer here full of activities!

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.

Luxurious Ski Retreat with Cozy Fireplace
Come stay in our cozy log cabin, Where the fire roars like a dragon. Just a hop, skip, and a jump away, From the slopes where you'll ski all day. Bring your furry friend, he'll love it too, We're dog-friendly, it's true, true, true. Luxury awaits in every room, From the plush beds to the bathroom. With nature all around, And peace and quiet to be found, This cabin is the perfect stay, For a fun and memorable holiday.

*Chalet In The Sky|2BR|Foliage|N.Conway|StoryLand
Embrace the beauty of fall in the White Mountains! 🍁 This cozy 2-bedroom chalet in Bartlett is perfect for families and friends. Wake up to crisp mountain views, enjoy modern comforts, and explore nearby favorites like Story Land and scenic White Mountains trails. Your autumn escape starts here! 🎢 Story Land -10 Min 🏞️ N.Conway Outlet Shopping-10 Min 🚠 Mt. Washington Auto Rd -35 Min
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

Rustic 3 Bedroom Chalet in Eidelweiss!

Heated SwimSpa, Sauna, Games + 7mi to Sunday River

Cozy cabin in the woods- great location

Spacious Mountain Chalet: Game Room & Pet-Friendly

Timberhaus Chalet | Charming • Clean • Comfortable

Modern Mountain Chalet Near Storyland & Jackson
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

Bethel home w/ Mtn Views, AC, HotTub, & FirePit

Cozy Chalet with Stunning Mountain Views

South Pond breathtaking mountain views! Hot tub/ga

Crystal Lake Chalet | Hot Tub, GameRoom+Wood Stove
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

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 | R4,252 ZAR | R3,509 ZAR | R3,353 ZAR | R2,800 ZAR | R4,321 ZAR | R3,907 ZAR | R4,926 ZAR | R4,702 ZAR | R3,302 ZAR | R4,477 ZAR | R4,149 ZAR | R4,304 ZAR |
| 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 R2,247 ZAR 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Jersey City Vacation rentals
- Island of Montreal Vacation rentals
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with outdoor seating Madison
- Rentals with lake access Madison
- Rentals with a fireplace Madison
- Rentals with a patio Madison
- Rentals with a hot tub Madison
- Rentals with a fire pit Madison
- Cabin rentals Madison
- Rentals with a kayak Madison
- Rentals with a washer and dryer Madison
- Waterfront rentals Madison
- Pet-friendly rentals Madison
- House rentals Madison
- Chalet rentals Carroll County
- Chalet rentals New Hampshire
- Chalet rentals United States
- Sebago Lake
- Squam Lake
- Story Land
- Scarborough Beach
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Cannon Mountain Ski Resort
- King Pine Ski Area
- Parsons Beach
- White Lake State Park
- Ferry Beach
- Cliff House Beach
- Laudholm Beach
- Waterville Valley Resort




