Family-friendly holiday rentals in Madison

4.94 out of 5 average rating, 116 reviews

Luxe Lodge in the Woods! With Sauna & Hot tub

Take it easy at this unique & tranquil getaway. This family-friendly Airbnb is packed with fun! A huge driveway welcomes your boat, snowmobiles, & toys. Inside, enjoy two living rooms with TVs & a basement games room with air hockey and foosball. Outdoors, relax in the wood-fired sauna or hot tub. Gather around the fire pit, or let the kids play on the swing set. With a cozy indoor fireplace, king, queen, & twin-over-twin bunks, it's the perfect escape for everyone. Adventure & relaxation await!

Indoor spacesFamilySleep quality

4.83 out of 5 average rating, 132 reviews

A spacious game room is featured, showcasing a pool table, a new ping pong table, and a foosball table. Comfortable seating is provided with a patterned couch, and natural light enters through several windows, illuminating the enjoyable game area.

Home in Madison

Spacious home near mountains and lakes

Enjoy this spacious home that includes 3 bedrooms, a great kitchen ( upgraded cookware), and a huge game room downstairs with a pool table, new ping pong table, and foose ball table. Within minutes, you can be on Silver Lake, North Conway, Storylalnd, Kangamangus or make a visit to the White Mountians . Shop at the Settlers green outlets. Enjoy the comfort of the newly installed central air! Located in a nice quiet neighborhood. Come and go skiing at King Pine or many others in the area.

FamilyIndoor spacesWalkability

4.91 out of 5 average rating, 161 reviews

A stone fire pit is surrounded by several wooden Adirondack chairs on a grassy area by the water. Trees provide partial shade, and the calm lake reflects the evening light. The warmth of the fire draws attention in the gathering space.

Cottage in Conway

Conway Waterfront Base for Your Family Memories!

Waterfront gem in the middle of it all! Designed to be the ideal getaway regardless of the season. Beautiful views out master bedroom, the back porch and from the backyard year round. The feel of seclusion while still being near all activities! Enjoy the water on one of the two kayaks or in the 2 canoes. Perfect base for skiing, hikes and sightseeing! Easy drive to North Conway, Kankamangus Highway, White Mountains, Story Land and so much more! No need to leave the property, just enjoy!

KitchenFamilyAccess

4.93 out of 5 average rating, 225 reviews

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

Cedar Hideaway: Walk to Pond, 15m N. Conway

Sip coffee on the screened porch listening to the wind in the pine grove. This modern cedar cabin is your sanctuary from the summer crowds, yet only 15 mins to the bustle of North Conway. Walk to the pond for a dip or read a book in the hammock. Equipped with fast WiFi and a fully stocked kitchen and charcoal grill. Cathedral Ledge and many hikes a short drive away. A tranquil, shady escape for those looking to slow down and breathe or your launchpad for White Mountain adventures.

Indoor spacesFamilyBeach

4.97 out of 5 average rating, 340 reviews

The exterior of the house features a rustic red wood siding with large windows, set within a lush green landscape. The sloped roof is adorned with a bright red metal covering, complementing the natural surroundings. Smooth stones lead up to the entryway, surrounded by carefully maintained grass and shrubs.

Home in Eaton

White Mt Retreat w/ Beach Pass, New Kitchen, W/D

Get away from it all in our lovely, spacious home with its new kitchen, in Eaton, only 15 min to the shops and restaurants in North Conway and five minutes to King Pine Ski Area. Our property comes with a lake access pass to Crystal Lake public beach. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home, with over 1600 sq. ft of living space, has two living room spaces providing private spaces for children and adults. We are owner-operated.

Indoor spacesFamilyCondition

4.97 out of 5 average rating, 182 reviews

A fire pit area is surrounded by several blue Adirondack chairs, arranged in a circle on a ground covered with natural earth. A hammock hangs between two trees, while string lights provide a soft glow overhead, creating an inviting space for gathering.

Home in Madison

The Getaway Chalet: Relaxation, Views & Fire Pit

Experience the ultimate mountain escape at The Getaway Chalet in Madison, NH. This spacious 4-bedroom retreat in the Eidelweiss community features breathtaking views, two living areas, and 1-Gig Fiber internet. Enjoy private beach access to three ponds or relax on the expansive deck. The highlight? Evenings spent at the private fire pit under the stars. Minutes from North Conway shopping and White Mountain ski resorts, it’s the perfect basecamp for your next 5-star adventure..

KitchenIndoor spacesHeating

4.96 out of 5 average rating, 100 reviews

The exterior of Valley View Farm is presented, featuring a charming white house with a sloped roof. A welcoming sign stands at the entrance, surrounded by colorful blooming flowers and greenery, with a gravel path leading up to the home under a bright blue sky.

Home in Freedom

Farmhouse Retreat, Dog Friendly w/ view & deck

Welcome to Valley View Farm, your next getaway! The 3-bedroom, 2.5-bath is newly remodeled with an open concept and modern vibe. Overlooking 90 acres with sprawling fields and 180-degree views of the Mount Washington Valley from Lake Ossipee to Chocorua Mountain. Enjoy your morning coffee while gazing out the wall-to-wall windows or take it outside to the expansive deck. Family and Dog-Friendly! Air Conditioning Summer '25 Minutes from Lake Ossipee. 25 mins to North Conway.

FamilyKitchenGetting around

4.9 out of 5 average rating, 123 reviews

The exterior of the spacious home presents a blend of stone and siding, surrounded by lush greenery. A paved driveway leads to the entrance, while the colorful sunset casts a warm glow across the landscape.

Home in Freedom

Our Mountain Retreat – Lake Ossipee Access

Spacious 5 bedroom home with convenient lake access, just a short walk or 5-minute drive to beautiful Lake Ossipee. Enjoy easy proximity to King Pine Ski Area and a quick 25-minute drive to Conway, where you'll find outlet shopping, scenic hiking trails, and a variety of restaurants. This property features a large yard with a fire pit, and a hot tub for ultimate relaxation. The master bedroom includes a private deck—perfect for morning coffee or stargazing at night.

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 108 reviews

A cozy bedroom features a patterned bedspread adorned with a bear design on a dark metal frame. A soft gray bench sits at the foot of the bed, and natural light filters through the window, complemented by sheer curtains.

Cottage in Conway

Central Location - Pet Friendly

Centrally located cottage minutes from all North Conway has to offer. Perfect for a romantic getaway or a vacation with the family, even the fur babies! The house has three bedrooms, full kitchen, dedicated workspace, full size washer/dryer and a large yard. Curl up on the couch and watch a movie or sit by the fire and star gaze. If you like adventures, there are many destinations nearby. The Pineside Cottage is wonderful for all year R&R. Book your stay today!

Indoor spacesFamilyCleanliness

Superhost

Chalet in Madison

Pond-Side Chalet • Private Beach • Canoe & Kayak

"So close to the water's edge you could practically fish from the deck." That's what guests say about Idylweiss Chalet, our pond-side chalet in Eidelweiss Village, 15 minutes from North Conway. Mornings on the deck with the loons calling across Little Pea Porridge Pond. Afternoons on the private sandy beach with the canoe and kayak. Sleeps seven across three bedrooms and two full bathrooms. A short drive to Storyland, ski resorts, and the Kancamagus Highway.

FamilyIndoor spacesDecor

4.8 out of 5 average rating, 150 reviews

4.98 out of 5 average rating, 112 reviews

Cabin in Madison

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.

KitchenIndoor spacesAmenities

4.92 out of 5 average rating, 262 reviews

Chalet in Madison

Chalet/close to N Conway, far enough away from all

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.

Indoor spacesFamilyGetting around

Popular amenities for Madison family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 184 reviews

Home in Tamworth

Pet-friendly cabin with hot tub and beach access!

Indoor spacesKitchenParks

4.96 out of 5 average rating, 145 reviews

A bright living area features a stone fireplace as the focal point, surrounded by large windows that allow natural light to fill the space. A comfortable sectional sofa and two leather armchairs are arranged around a coffee table on a textured rug, creating a welcoming atmosphere.

Villa in Conway

Luxurious Retreat with Hot Tub & Walk to Echo Lake

FamilyKitchenLocation

Superhost

A hot tub bubbles gently, surrounded by towering trees and a serene view of Moose Pond. The water reflects the clear blue sky and is framed by a tranquil landscape, creating a peaceful atmosphere for relaxation.

Cabin in Bridgton

Waterfront,Hot tub,Private dock,Freshly renovated

FamilyIndoor spacesHeating

4.82 out of 5 average rating, 190 reviews

Superhost

A wooden dock extends over the calm waters of Chocorua Lake, framed by lush greenery. Tall trees line the shore, and a mountain rises in the distance under a clear blue sky, creating a serene outdoor setting.

Home in Tamworth

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

KitchenIndoor spacesSleep quality

4.82 out of 5 average rating, 125 reviews

5.0 out of 5 average rating, 103 reviews

Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

Indoor spacesFamilyLayout

4.96 out of 5 average rating, 121 reviews

A hot tub is surrounded by wooden beams and an overhanging roof, providing shelter while enjoying views of the mountains. An outdoor TV is mounted nearby, with scenic landscapes visible in the background. Bubbles can be seen rising in the crystal-clear water.

Townhouse in Conway

North Conway Sunsets Mountain Views with Hot Tub

FamilyKitchenWi-Fi

4.99 out of 5 average rating, 138 reviews

Home in Bridgton

Family & Friends Retreat*Hot Tub*Game Room*King Be

KitchenIndoor spacesHospitality

4.91 out of 5 average rating, 145 reviews

A private courtyard is illuminated at night, featuring a hot tub and a fire pit surrounded by gravel. Four wooden chairs are arranged around the fire pit, which has a glowing flame. Soft lights are strung along the wooden fence and cabin walls, creating a cozy atmosphere.

Cabin in Conway

Troy’s Cabin: N. Conway w/ Hot Tub, A/C, Fireplace

Indoor spacesFamilyCheck-in

Family- and pet-friendly home rentals

A modern mountain home constructed with wood and stone accents is shown from the front, surrounded by tall trees. A paved driveway leads up to the welcoming entrance, which features a set of stairs and a covered porch.

4.99 out of 5 average rating, 167 reviews

Dog & family friendly, close to Conway & Cranmore

FamilyKitchenSleep quality

4.96 out of 5 average rating, 201 reviews

A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.

Cabin in Conway

The Conscious Cabin | Getaways + Retreats

KitchenIndoor spacesAccuracy

4.94 out of 5 average rating, 153 reviews

Chalet in Conway

Lost Compass Cabin•Firepit•River• Mountains

FamilyIndoor spacesCheckout

4.85 out of 5 average rating, 121 reviews

Private & Spacious, 9 Miles to downtown N. Conway

Indoor spacesFamilyNearby

4.79 out of 5 average rating, 225 reviews

The cabin features a unique architectural design with a mix of slanted roofs and wooden siding. Large windows allow natural light to fill the building, while a welcoming front porch is accessed by steps. Surrounding greenery enhances the cabin's serene setting.

Cabin in Tamworth

Cabin in the Pines, Lakes Region / White Mountains

Indoor spacesFamilyHeating

A spacious dining area features a wooden table set for meals, adorned with decorative placemats and a vase of flowers. The adjoining living area is illuminated by natural light, showcasing a cozy sectional sofa and a wooden coffee table. A stone wall adds texture to the space.

4.9 out of 5 average rating, 106 reviews

White Mountain Mansion -Secluded property, pets OK

Indoor spacesKitchenBackyard

4.96 out of 5 average rating, 102 reviews

A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.

Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

Indoor spacesFamilyHiking

4.9 out of 5 average rating, 102 reviews

A charming chalet is surrounded by trees, featuring a large deck with a wooden railing and steps leading down to the yard. Soft outdoor lighting is visible, enhancing the outdoor space. The angled roof design adds character to the home, complemented by a central brick chimney.

Chalet in Tamworth

Comfortable chalet in Tamworth, walk to lake

KitchenFamilyView

Family-friendly home rentals with a pool

Townhouse in North Conway

The open kitchen features modern stainless steel appliances, including a refrigerator and stove. A spacious island with Quartz countertops provides seating for four, complemented by white bar stools. The dining area is visible, showcasing a dining table set for six, with natural light flowing in from nearby windows.

Family friendly + Mountain Views @amountainplace

Indoor spacesFamilyCheck-in

4.96 out of 5 average rating, 399 reviews

A serene view of a calm river surrounded by lush greenery. Gentle slopes lead to sandy banks, while trees provide a natural border on either side. The water reflects the blue sky above, creating a peaceful ambiance ideal for outdoor relaxation.

4.91 out of 5 average rating, 149 reviews

Cozy Family Retreat with Saco River Access

KitchenFamilyHospitality

4.96 out of 5 average rating, 218 reviews

The living area features a neutral color palette with a comfortable sectional sofa and a small dining table. A flat-screen TV is positioned adjacent to a gas fireplace, enhancing the space's coziness. Light spills in through the sliding glass doors, revealing a wooden deck and seasonal outdoor scenery.

Townhouse in Conway

Trail side townhome

KitchenFamilyLaundry

A cozy living area is furnished with a light green sectional sofa and a comfortable armchair. Natural light enters through sliding glass doors, which lead to a deck. A decorative area rug is laid over hardwood flooring, and a brick fireplace adds warmth to the space.

4.98 out of 5 average rating, 199 reviews

3BR, 2BA condo in No. Conway, Close to everything!

Indoor spacesFamilyQuiet

The open layout features a dining area with a rustic table and comfortable seating for six. A cozy sectional sofa is positioned near a door leading to the outdoor patio. Soft lighting and decorative elements create a welcoming and homey environment.

4.98 out of 5 average rating, 125 reviews

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

KitchenIndoor spacesSleep quality

4.93 out of 5 average rating, 126 reviews

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

FamilyKitchenDecor

Townhouse in North Conway

A spacious living area features a gray sectional sofa and a round chair, complemented by a wooden coffee table. Wall decor includes vintage snowshoes and framed artwork, while a stone fireplace adds warmth. Light filters in, enhancing the welcoming atmosphere.

Family Ready Home Close to Town Trails and Outlets

FamilyKitchenLaundry

4.95 out of 5 average rating, 235 reviews