
Chalet holiday 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.

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.

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 Chalet near a Lake
Enjoy this unique A-Frame Chalet in the coveted Mountain Lakes District of NH just 4 miles outside the White Mountains National Forest. Within 30 minutes to Cannon and Loon Ski Resorts and world famous Franconia Notch State Park, this cozy home gives you all the feels of a mountain lifestyle without giving up any comfort. Sun bathe and barbecue out back on the private decks. Dont foget to relax with a unique nature-surrounded experience in the hot tub! A short walk to a beautiful lake view.

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!

Breathtaking mountain views - Hidden gem!
Chalet in the Clouds!⛅️ Month to Month lease available. Relax & Rejuvenate w/ panoramic views of White Mountains from any of the 4 decks of Kailaśa Chalet! Perched on top of a mountain overlooking Mt Chocorua & Silver Lake w/ majestic views of Mt Washington Valley. So easy to get lost in the beauty of Kailaśa! Wake up to the experience of being above the clouds overlooking the valley! Settle down after dinner around the stone fireplace while watching your favorite shows on 65" TV

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.

Cozy Mountain Cabin in Jxn! Views & Dog friendly
A perfect retreat to slow down, watch the first snow dust the pines, and feel tucked-away from the world. ❄️ Jackson XC Ski: under 5 min drive ❄️ Black Mountain: under 10 min drive ❄️ Wildcat & Attitash: 15 min drive If you're looking for an intimate and cozy getaway home with a mountain view, look no further! Rustic meets modern chic, the cabin is adorned with everything you need to relax and unwind!

Gas fireplace + stargazing deck 4 mins from skiing
Welcome to The Aspen Chalet, our cozy retreat in the White Mountains. ➔ Central spot: 4 mins to Attitash + Storyland ➔ 10 mins to downtown North Conway ➔ Access to Saco neighborhood beach (.5 miles) ➔ Cranmore (12 mins) + Black Mountain (10 mins) ➔ Mount Washington + Wildcat (30 mins) ➔ Walkable to Mt Stanton Trailhead (.8 miles) ➔ Diana's Baths (8 mins) + Cathedral Ledge (11)

A-Frame w/ Hot Tub 5 minutes from Gunstock
Our A-Frame 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 chalet rentals in Madison
Family-friendly chalet rentals

Cozy den- great winter getaway w hot tub/fireplace

Cozy Cabin| Near Ski| Fireplace|EV charger

The Gem of Linderhof

Rustic 3 Bedroom Chalet in Eidelweiss!

3 min to Sunday River w/ Views, Game room, Hot tub

Timberhaus Chalet | Charming • Clean • Comfortable

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

Madison Hot Tub Chalet, Dog Friendly, Beach Access
Luxury chalet rentals

Peaceful Chalet in the White Mountain, Sleeps 15

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

85in TV | Hot Tub | Huge Deck | Game Room | Playhouse

White Mountain Hideaway: Chic North Conway Chalet

Maine A-Frame with Hot Tub, Game Room, Lake Access

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

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

East Branch Chalet (7 min to N Conway)
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.

Waterfront/Private Dock/HotTub/Pool & Amenities

Gorgeous Four Seasons Loon Chalet at Locke Lake

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 | $318 SGD | $262 SGD | $251 SGD | $209 SGD | $323 SGD | $292 SGD | $368 SGD | $351 SGD | $247 SGD | $335 SGD | $310 SGD | $322 SGD |
| 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 holiday rentals
Explore 10 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $168 SGD per night before taxes and fees

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

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
10 of Madison holiday rentals include wifi 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 Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Rentals with outdoor seating Madison
- Rentals with a firepit Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with lake access Madison
- Pet-friendly rentals Madison
- Rentals with a washing machine and dryer Madison
- Waterfront rentals Madison
- Rentals with a fireplace Madison
- Rentals with a kayak Madison
- Cabin rentals Madison
- Rentals with a hot tub Madison
- Rentals with a patio Madison
- House rentals Madison
- Chalet rentals Carroll County
- Chalet rentals New Hampshire
- Chalet rentals United States
- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Scarborough Beach
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Franconia Notch State Park
- East End Beach
- Tenney Mountain Resort
- Diana's Baths
- Omni Mount Washington Resort
- Dunegrass Golf Club
- King Pine Ski Area
- Willard Beach
- Cannon Mountain Ski Resort
- Funtown Splashtown USA
- Cliff House Beach
- Waterville Valley Resort
- Parsons Beach
- Ferry Beach
- Laudholm Beach
- White Lake State Park




