
Chalet holiday 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.

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 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

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 cabin with views, privacy, and more.
Cabin in the woods with amazing mountain views. Situated on 2.5 acres and surrounded on 3 sides with 30 additional steep wooded acres; peace and privacy. NOTE: winter driving will require snow tires or 4wheel drive as the house is on an incline road. Skiing, Snowboarding: - 25 minute drive to Loon Mountain - 25 minute drive to Waterville Valley (discounted lift tickets available) Cabin professionally cleaned between stays w/extra attn on high touch areas.

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.

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!

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.

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 chalet rentals in Madison
Family-friendly chalet rentals

Ski-In/Ski-Out Attitash! Cozy Chalet! Dog Friendly

Cozy Cabin| Near Ski| Fireplace|EV charger

Rustic 3 Bedroom Chalet in Eidelweiss!

Cozy cabin in the woods- great location

Cozy Chalet with beach access

Modern Mountain Chalet Near Skiing & Attractions

Timberhaus Chalet | Charming • Clean • Comfortable

Renovated Modern Chalet - Swim, Hike, Shop, Dine!
Luxury chalet rentals

Peaceful Chalet in the White Mountain, Sleeps 15

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

Bear Ridge Lodge

Idyllic Mountain and Lake Getaway

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

White Mountain Hideaway: Chic North Conway Chalet

Charming Chalet 3 min to SKIING & PVT beach access

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

Charming & Cozy 3 Bedroom Chalet

Pondside Getaway - Fishing, Canoeing, & Skiing

The Chalet~ 4 bed Lakefront Family Vacation

Waterfront/Private Dock/HotTub/Pool & Amenities

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 | € 210 | € 173 | € 166 | € 138 | € 213 | € 193 | € 243 | € 232 | € 163 | € 221 | € 205 | € 213 |
| 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 € 111 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!
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- 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
- King Pine Ski Area
- Dunegrass Golf Club
- Willard Beach
- Funtown Splashtown USA
- Cannon Mountain Ski Resort
- Waterville Valley Resort
- Parsons Beach
- Cliff House Beach
- Ferry Beach
- Laudholm Beach
- White Lake State Park




