
Family-friendly holiday rentals in Madison
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Madison

Total holiday rentals
Explore 150 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 7,920 verified reviews to help you choose

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
150 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!
Top-rated family-friendly rentals in Madison
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

The Conscious Cabin | Getaways + Retreats
Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.
4.96 out of 5 average rating, 201 reviews
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.
4.83 out of 5 average rating, 133 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.
4.98 out of 5 average rating, 127 reviews
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.
4.94 out of 5 average rating, 231 reviews
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.
4.97 out of 5 average rating, 340 reviews
White Mountain Mansion -Secluded property, pets OK
Tucked away on five acres of beautiful wooded mountain land, we have our beautiful 5 bedroom, 5 bathroom home. 10 min outside of North Conway! Not only do we have all common amenities, we have some pretty special ones too: a movie theatre room, a gym, surround sound in 3 rooms, an upstairs lounge area equipped with a Billiards, Ping Pong, and a poker table! Not to mention a beautiful wood burning fireplace, and extra sleeping options for guests (that aren’t factored into bedrooms)
4.9 out of 5 average rating, 106 reviews
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..
4.97 out of 5 average rating, 183 reviews
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.
4.96 out of 5 average rating, 101 reviews
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!
4.98 out of 5 average rating, 111 reviews
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.
4.79 out of 5 average rating, 152 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.
4.98 out of 5 average rating, 112 reviews
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.
4.92 out of 5 average rating, 263 reviewsPopular amenities for Madison family-friendly rentals
Family-friendly home rentals with a hot tub

Luxe Lodge in the Woods! With Sauna & Hot tub
4.94 out of 5 average rating, 120 reviews
Gorgeous Conway Home A/C, Hot Tub & Full Game Room
4.92 out of 5 average rating, 100 reviews
Our Mountain Retreat – Lake Ossipee Access
4.9 out of 5 average rating, 123 reviews
One-of-a-kind log home
4.9 out of 5 average rating, 167 reviews
*New Luxe Mountain Escape* HotTub~Sauna~Games!
4.99 out of 5 average rating, 131 reviews
Luxurious Retreat with Hot Tub & Walk to Echo Lake
4.96 out of 5 average rating, 145 reviews
White Mtn Lux Retreat | Hot Tub, Sauna & Game Room
4.95 out of 5 average rating, 101 reviews
*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.
4.95 out of 5 average rating, 174 reviewsFamily- and pet-friendly home rentals

Dog & family friendly, close to Conway & Cranmore
4.99 out of 5 average rating, 169 reviews
Lost Compass Cabin•Firepit•River• Mountains
4.93 out of 5 average rating, 160 reviews
Red Shed Cottage at Pickett Hill Farm
4.96 out of 5 average rating, 105 reviews
Bear Ridge Lodge
4.95 out of 5 average rating, 353 reviews
Spacious 3 bedroom Mountain Chalet -Conway, NH
4.94 out of 5 average rating, 117 reviews
Private & Spacious, 9 Miles to downtown N. Conway
4.85 out of 5 average rating, 121 reviews
Mountain View Studio
4.98 out of 5 average rating, 688 reviews
Cabin in the Pines, Lakes Region / White Mountains
4.79 out of 5 average rating, 225 reviewsFamily-friendly home rentals with a pool

Family friendly + Mountain Views @amountainplace
4.96 out of 5 average rating, 405 reviews
Cozy Family Retreat with Saco River Access
4.91 out of 5 average rating, 149 reviews
Family Ready Home Close to Town Trails and Outlets
4.95 out of 5 average rating, 237 reviews
Trail side townhome
4.96 out of 5 average rating, 220 reviews
Cozy Condo at Attitash!
4.91 out of 5 average rating, 209 reviews
3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
4.98 out of 5 average rating, 125 reviews
NoCo Village King/kitchenette
4.91 out of 5 average rating, 261 reviews
3BR, 2BA condo in No. Conway, Close to everything!
4.98 out of 5 average rating, 199 reviewsWhen is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $337 SGD | $353 SGD | $288 SGD | $279 SGD | $331 SGD | $332 SGD | $333 SGD | $322 SGD | $281 SGD | $313 SGD | $296 SGD | $336 SGD |
| 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 |
Destinations to explore
- Cabin rentals Madison
- Rentals with beach access Madison
- Rentals with lake access Madison
- Pet-friendly rentals Madison
- Chalet rentals Madison
- Waterfront rentals Madison
- Rentals with a kayak Madison
- Rentals with a hot tub Madison
- House rentals Madison
- Family-friendly rentals Carroll County
- Family-friendly rentals New Hampshire
- Family-friendly rentals United States
- Sebago Lake
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Willard Beach
- Scarborough Beach
- Mount Washington Cog Railway
- Santa's Village
- Sunday River Resort
- Cranmore Mountain Resort
- Hills Beach
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Pleasant Mountain Ski Area
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Attitash Mountain Resort
- Echo Lake State Park
- Crawford Notch State Park





