Family-friendly vacation rentals in Madison

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Top-rated family-friendly rentals in Madison

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The living area features wooden walls and a cozy sofa accented with colorful pillows. A lighted table sits beside a small lamp. The kitchen is visible in the background, showcasing modern fixtures and glassware.

Cabin in Conway

4.92 out of 5 average rating, 378 reviews

N. Conway…Cozy Cabin, Centrally Located

Our newly renovated cabin is family friendly (childproofed), stylish, and cozy with lovely wooden accents throughout! It is newly furnished and has brand new mattresses! This cabin is wonderfully located just off of Westside Rd. a mere skip away from Echo Lake, Cathedral Ledge, Diana's Baths etc...It is a 5 - 8 minute drive to North Conway Village and Cranmore Ski Resort; and a 5 - 8 minute drive from Settler's Green Outlets, grocery stores etc...with numerous other popular destinations nearby.

Guest favorite

A relaxed outdoor area features wooden Adirondack chairs arranged around a fire pit, with smooth stones providing a natural border. A kayak rests on the sandy shore next to the calm water, while a charming two-story chalet is visible in the background, surrounded by trees.

Chalet in Madison

4.84 out of 5 average rating, 108 reviews

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.

Guest favorite

A modern cabin exterior is surrounded by lush greenery, featuring a spacious outdoor area with a fire pit at the center. Four wooden chairs are arranged around the fire pit, while a picnic table is nearby. String lights are hung to enhance evening ambiance.

Cabin in Madison

4.94 out of 5 average rating, 185 reviews

Adorable cedar cabin hideaway

Our cozy, warm cabin is set in a tranquil, picture perfect pine grove. A three minute walk to Davis Pond and 15 minutes from North Conway and ski resorts. The perfect getaway spot whether you need to unplug or plan an adventure. The home is comfortable and modern without compromising the rustic White Mountain charm, outfitted with all the amenities, a work station and a full outdoor space. We have put a lot of thought into this space and are confident that it will translate into a magical stay.

Top guest favorite

A large window offers a view of rolling mountains adorned with colorful autumn foliage. Shades of red, orange, and yellow contrast against the green trees, while a winding path is visible in the foreground, leading into the vibrant landscape.

Guest suite in Conway

4.98 out of 5 average rating, 581 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

Guest favorite

A spacious room features a cozy bed covered with a patterned quilt, accented by a black pillow. Two windows allow natural light to fill the space, flanked by blue curtains. A vintage dresser and a bookshelf are positioned nearby, enhancing the welcoming ambiance.

Guest suite in Albany

4.89 out of 5 average rating, 450 reviews

Mountain Hideaway

Two private rooms with full bath in private home. Includes separate entrance sharing only a mud room. Downstairs room has a refrigerator, microwave, and toaster oven, coffee and tea provided. Located in a beautiful rural setting with mountain views adjacent to the National Forest and Tin mt conservation center. Only 1 mile from the Kancamangus Highway, route 16 and Conway. Minutes from outdoor activities: skiing, biking hiking, paddling and snowshoeing. Many restaurants and shops nearby.

Guest favorite

A compact kitchen area is shown, featuring a full-size refrigerator, stove, and sink with countertop space. Cabinets are installed above and below the counter. A cozy futon couch is positioned in the foreground, complementing the warm wooden paneling on the walls.

Home in Albany

4.83 out of 5 average rating, 484 reviews

Cozy Guest Suite in White Mountain National Forest

Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

Top guest favorite

The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.

Apartment in Wakefield

4.98 out of 5 average rating, 106 reviews

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Top guest favorite

A cozy cottage is framed by lush greenery and colorful landscaping, featuring a welcoming front porch and a sunroom with large windows. A picnic table is positioned nearby, inviting outdoor relaxation. The property is set against a backdrop of trees, contributing to a private and serene environment.

Cottage in Brownfield

4.99 out of 5 average rating, 268 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Top guest favorite

The two-story mountaintop home is framed by lush greenery and features a spacious deck with a red umbrella. Stacked firewood is neatly arranged under the deck, and large windows allow natural light to illuminate the interior.

Home in Madison

4.97 out of 5 average rating, 158 reviews

Beautiful Getaway Chalet - Mountain Views!

Private mountaintop home! My home is located in the beautiful community of Eidelweiss with private beaches, swimming, and a playground. Located minutes from North Conway and close to all Mount Washington Valley ski areas, activities, and tax-free shopping. Just a two-hour drive from Boston and you're ready to experience crystal clear rivers, pristine lakes, covered bridges, majestic mountains, picturesque hiking, and numerous local attractions and parks.

Top guest favorite

A charming log cabin is surrounded by lush greenery and tall trees. The building features a welcoming front porch with steps leading up to the entrance. Flowering shrubs and a well-maintained garden area enhance the cabin's natural setting.

Cabin in Madison

4.98 out of 5 average rating, 103 reviews

Little Bear Lodge | Cozy Log Cabin in the Pines

Escape to the Little Bear Lodge located in the heart of the White Mountains! Brimming with charm and character, this quintessential log cabin provides plenty of space for the whole family in a private, idyllic mountain setting. Bring your bags & leave everything else to us. Fully stocked kitchen & coffee bar, cozy living room, and spacious bedrooms. Lots of outdoor space too - a screened in porch, deck, patio and beautiful landscaping.

Top guest favorite

The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.

Guest suite in Conway

5 out of 5 average rating, 351 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Guest favorite

A charming cottage is nestled among tall pine trees, with a black metal roof. It features a welcoming front porch and a natural wood pathway that leads to the water's edge. The serene pond is visible beyond the cottage, framed by lush greenery.

Cottage in Conway

4.95 out of 5 average rating, 377 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!