
Family-friendly vacation rentals in Madison
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Madison
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

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.

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.

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.

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!

Luxurious Mountainside Cabin! Fantastic Views!
Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets Welcome! *Pet Fee Applies! *Additional Fee for Sauna

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.

Secluded, cozy cabin nestled in the Maine woods
Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

Mountain Treehouse Guesthouse
Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

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.

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.
Popular amenities for Madison family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Suite Jacuzzi Pool White Mtns. River Front

Attitash Studio | 5min to Storyland| Pools

Mountain-view ski chalet w/ hot tub

Hot Tub Haven: Dog-Friendly Retreat

Romantic New England Historic Schoolhouse c1866

An Amazing Mountain Getaway!

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

Family Friendly Chalet with Serene Mountain Views
Family- and pet-friendly home rentals

Tree House at the Shire

Handcrafted A-Frame near Newfound Lake & Hiking

Lost Compass Cabin - Close to shops & downtown

Tranquility, Relaxation, Family, Romance

The Conscious Cabin

Steep Falls Escape, river & falls just steps away

The Watson House

Rustic Pebble Cottage in beautiful Bridgton, Maine
Family-friendly home rentals with a pool

Cranmore Condo | Pool, Hot Tub & Minutes to Town

White Mountain Resort Pool/HotTub Shuttle to Loon

AttitashResort! 1-flr, studio, secure check-in

Family friendly + Mountain Views @amountainplace

KimBills’ on the Saco

Cozy Condo at The Seasons- 2 Bedrooms

Loon Mountain Area Rental - 2Br/2Ba

Trail side townhome
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $317 CAD | $338 CAD | $282 CAD | $275 CAD | $297 CAD | $319 CAD | $368 CAD | $355 CAD | $310 CAD | $352 CAD | $293 CAD | $334 CAD |
| 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 vacation rentals that are family-friendly in Madison

Total vacation rentals
Explore 160 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 7,310 verified reviews to help you choose

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
150 of Madison vacation 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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- Sebago Lake
- Squam Lake
- Story Land
- Scarborough Beach
- Sunday River Resort
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Tenney Mountain Resort
- Funtown Splashtown USA
- King Pine Ski Area
- Willard Beach
- Cannon Mountain Ski Resort
- Cliff House Beach
- Parsons Beach
- Waterville Valley Resort
- Ferry Beach
- White Lake State Park
- Laudholm Beach




