
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 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!

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.

*NEW Chalet in the Sky|2BR|Cranmore|North Conway
❄️ Embrace the beauty of winter in the White Mountains! ⛄ This cozy 2-bedroom chalet in Bartlett is perfect for families and friends. Wake up to snowy mountain views, enjoy modern comforts, and explore nearby favorites like Story Land and scenic White Mountains trails. Your winter escape starts here! ⛷️ Attitash Mountain Resort - 10 min drive 🏔️ Cranmore Mountain Resort - 10 min drive ❄️ Wildcat Mountain - 30 min drive ✨ Santa's Village-30 Min drive

Romantic Winter Cabin • Fireplace • Mountain View
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.

Good Friday Chalet | Walk to Village + Cranmore Mt
LOCATION! LOCATION! LOCATION! The perfect vacation getaway in the center of North Conway! Located less than a mile walk to the village's restaurants and shops, yet nestled away from the hustle and bustle of the strip. Lounge outdoors by our fire pit (Seasonal May-Oct). Furry friends are welcomed! (Please include them as part of your guest selection, thank you).
Popular amenities for Madison chalet rentals
Family-friendly chalet rentals

Cozy den- great winter getaway w hot tub/fireplace

Alpine Perch - NEW Renovated (May 2025)

Idyllic Mountain and Lake Getaway

Lake Ossipee Village, Freedom, NH

Cozy Cabin| Dog Friendly |Fire Pit| EV charger

Charming Chalet 3 min to SKIING & PVT beach access

The Chalet~ 4 bed Lakefront Family Vacation

Rustic 3 Bedroom Chalet in Eidelweiss!
Luxury chalet rentals

Peaceful Chalet in the White Mountain, Sleeps 15

SKI IN/OUT Pleasant Mountain 3* bedrooms 2.5 baths

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

6 BR | EV Charger | No Pet Fee | Pool Table

Ski & Lake Retreat w/ Epic Views

Red Ridge | 3BR, Pet-Friendly, North Conway Fun

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

East Branch Chalet (7 min to N Conway)
Lakefront chalet rentals

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 | $246 | $203 | $194 | $162 | $250 | $226 | $285 | $272 | $191 | $259 | $240 | $249 |
| Avg. temp | 6°F | 6°F | 13°F | 24°F | 36°F | 46°F | 50°F | 49°F | 43°F | 31°F | 21°F | 12°F |
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 $130 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
- Sunday River Resort
- Scarborough Beach
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Franconia Notch State Park
- East End Beach
- Omni Mount Washington Resort
- Diana's Baths
- Tenney Mountain Resort
- Dunegrass Golf Club
- King Pine Ski Area
- Willard Beach
- Funtown Splashtown USA
- Cannon Mountain Ski Resort
- Cliff House Beach
- Waterville Valley Resort
- Parsons Beach
- Ferry Beach
- White Lake State Park
- Laudholm Beach
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