Chalet vacation rentals in Madison

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Top-rated chalet rentals in Madison

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Guest favorite

Chalet in Bartlett

4.98 out of 5 average rating, 130 reviews

Relaxing Chalet w/ fireplace, close to Mnts

Seeking adventure or relaxation? There is something for everyone here! Come in through the bright spacious mudroom to shed your things. Walk up to the main living area on the custom white oak live edge staircase. Enjoy an open concept floor plan where you can make your favorite drink, brew a cup of coffee and enjoy. Relax on the large front deck after a day in the White Mountains or the private beach. The peaceful glow of the firepit with views of Mount Stanton is the perfect ending to the day.

Guest favorite

Chalet in Denmark

4.91 out of 5 average rating, 100 reviews

Relaxing A-Frame with Hot Tub and 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 also! 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. Kayaks and hot tub provided! Come experience our slice of heaven for yourself, you won’t regret it!

Guest favorite

Chalet in Fryeburg

4.94 out of 5 average rating, 222 reviews

Cozy Chalet*HOT TUB*Pets*<30 min N. Conway&Skiing

The LV Chalet is located less than 30min to popular North Conway, N.H./15 min to Historic Fryeburg, Maine. The Chalet is ideal for couples, friends & families to relax! In the Summer, enjoy beach access to Lower Kimball Lake, nearby Saco River and year round hiking trails. In the winter, the Chalet is situated between ski mountains: Cranmore Mountain & Pleasant Mountain. There’s also close access to Snowmobile trails. Whatever your vacation interests are; the area boasts it all! No partying pls

Guest favorite

Chalet in Freedom

4.93 out of 5 average rating, 194 reviews

Cute cottage with lake access at beach club.

My entire house just waiting to be enjoyed! A great get away for relaxing. King Pine ski hill is close by for winter fun. Summertime, I am a member of the Lake Ossipee Village Beach Club on Broad Bay, the most sandy beach with facilities. Enjoy the beach! Nearby, Freedom Town Forest trails await hiking/biking or Goodhue Boat Co. has boat rentals. If shopping is a must, Conway is 20 minutes north as are other ski hills. Antique/resale shops are nearby. Guests love the updated décor.

Guest favorite

Chalet in Jackson

4.95 out of 5 average rating, 107 reviews

Spectacular 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.

Guest favorite

Chalet in Franconia

4.95 out of 5 average rating, 279 reviews

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.

Guest favorite

Chalet in Intervale

5 out of 5 average rating, 126 reviews

Valley Vista: Epic views, hot tub, family friendly

Escape to the mountains and enjoy luxurious comfort at Valley Vista Lodge! You’ll enjoy panoramic White Mountain views, a covered & private hot tub where you can stargaze, and family-friendly amenities with room for the whole family (or two!) in over 3,000 sq. ft of living space. Our home is a 3 minute drive from Story Land, and close to stellar skiing (10 minutes to Attitash & Cranmore, 20 to Wildcat) and shopping (10 minutes to downtown North Conway, 15 to Settlers Green).

Guest favorite

Chalet in Naples

4.96 out of 5 average rating, 104 reviews

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.

Guest favorite

Chalet in Conway

4.95 out of 5 average rating, 134 reviews

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.

Guest favorite

Chalet in Madison

4.93 out of 5 average rating, 227 reviews

Eidelweiss Chalet/1 min walk to pond/playground

Please read our Coronavirus cleaning update. Quaint and cozy chalet located about 5 minutes from Conway and the hub of the White Mountains. As you pull into our neighborhood you notice several chalets on a paved road, winding up and over hills. Pull into our large carport to find our two level chalet that you have rented. The sounds of the babbling brook greet you as you exit your car with the inviting seating on both decks.

Guest favorite

Chalet in Bartlett

4.96 out of 5 average rating, 158 reviews

Ski chalet w/ fireplace 4 mins from Attitash

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)

Superhost

Chalet in Gilford

4.82 out of 5 average rating, 274 reviews

A-Frame w/ Hot Tub 5 minutes from Gunstock/ Lake

Our A-Frame is just minutes from Gunstock Mountain Resort and the Gilford town beach at Lake Winnipesaukee. Three bedrooms can accommodate up to 7 guests, with 2 queens, 1 full and 1 twin bed, and 1.5 bathrooms. Outdoor area includes a hot tub, fire pit, table/seating, a gas grill and plenty of parking. 1 mile from Bank NH Pavillion and 5 miles from Weirs Beach.