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

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Quiet Condo Close to Shopping and Attractions
Amazing place! Clean, lots of amenities, and the place had all the basics you could need! I will definitely be referring friends and returning for future trips!

The Overlook/Cozy 2 bed/Hot Tub/Wood Stove/Firepit
Wished we did more than one night at Scott's place! It's definitely equipped to spend more time. The two full bathrooms was a huge plus and the first floor one was super private for added comfort. Excellent water pressure, the hot tub was pristine and maintained, and so was the sauna. Despite the hot weather we used both and loved this perk! Bed in the main bedroom (the only one we used) was very comfortable and felt clean. Having to do laundry in the morning was a bit non-vacation-y feeling but easy enough. Great stay overall!

Owl-Pine Ski Lodge: Rustic Cabin w/Hot Tub
The cabin was beautiful and spacious. Definitely can see all the updates and renovations that have been made. Rustic but with all the modern comforts. We were only there a couple of days but fit in an outdoor fire pit and hot tub! Wish we had a few more days off to enjoy more- but we made the most of it. I take any family time i can get! Thank you!

Million $ View of Lake Winni Flexible check in/out
The place was great. Quiet with beautiful views. Lots of games which was helpful because it rained a lot during our stay. 10/10 would recommend and stay again. Host was very helpful and kind. The woman that cleaned the pool was also very sweet. My 8 year old was itching to swim in the freezing pool when it wasn’t quite ready and she offered to come to our room and let us know when she was done. Thank you for having us!

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

EPIC VIEWS, Hot Tub, Pond, River, 14 Acres A Frame
Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10

Maine Lakes Region house (private hot tub)
The spot was perfect for a weekend of skiing and riding snowmobiles. Exactly what we were looking for in a vacation home. Paul was great at recommending places and his response time was great. Also the wood burning stove made the weekend cozy and perfect.
Family- and pet-friendly home rentals

Large and lovely mountain cabin near North Conway
We had a great weekend with a blended family of young adults! There was hiking and visiting family also visiting while there! Great space and location!

Lily Brook Farm, Hollis, Maine
Visited Feb '25 Steep stairs {a delightful New England quirk} lead to a comfortable bed, quaint views out the window. Soft cottage core vibes. Eclectic design steeping in a life well lived. Wonderful kitchen, well stocked and easy to cook in. Shower pressure is adequate. Bathroom is clean and filled with an array of books and tchotchkes. Your eyes always have something to wander and examine. It's a maximalists dream. The book shelf in the living room is filled with old books some titles are expected due to surroundings and some are just plain fun. May I recommend a game of I spy Nina is quite fantastic. A spit fire. An attentive host. Hospitable and kind. She gave it a welcoming vibe. Meeting her animals was truthfully a highlight. They are even tempered and kind. Her horse is stunning & social. The donkey a goof. The mule is oh so friendly. Sheep a bit shy but non the less beautiful. Chickens? fluffy feet! The ducks were personable. The goats, joyful. Cat, adorable. Good workin dogs.

UpCountry Guest House in Heart of North Conway NH
Doug is a great host and his home is so cozy- it feels like a family home. Our 2 dogs were welcomed and we felt at ease. The area is residential and quiet. Super easy to everything you need.

Sweet 2 bedroom apartment
This is the kind of airbnb I'm excited to visit and support -- really lovely, cozy place with a lot of character and everything we needed to make ourselves at home for a week. The proximity to Chocorua is fantastic and it's a good spring board to the lakes region & and the White Mountains. Becky is fantastic - super friendly, responsive, and kind. The wifi was strong enough for me to work there for a few days and we had all the supplies we needed to cook for ourselves. The only issue was the road noise, which was pretty loud during the day, but thankfully quieter in the nights.

Cottage with antique charm view & river HSI Wi-Fi
We loved our stay! It ended up being a rainy weekend so we really enjoyed all the little extras the cabin had to offer - especially the crafting cabinet! The house has all these little helpful notes about how best to enjoy the house and your stay. The backyard is beautiful, the kitchen had great little additions (we always forget olive oil!). The beds were comfortable, our kids loved the bunk bed room. The location is great, close to local shops and small treasures but also near big chains should you need a specific item. The house really makes the most of the space. We will definitely be back!

Mountain River Spacious Country Stu
We had a wedding to attend at The Barn on the Pemi. Vikis place is literally only a 4 min drive away! Great place to stay for any event here. Very peaceful !

Cozy Cottage w/ Mountain Views & Two Outdoor Decks
Outstanding cottage! It had everything we needed and the hosts were very responsive and acommodating. We look forward to visit again!

Mountain View Cabin #1
Always a great stay at Jeff and Jayne's cabin. I think this was our 8th stay here and as always, a wonderful place to stay near Gunstock and Lake Winnipesauke.
Family-friendly home rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

★Spacious, Updated, Beautiful Condo @ The Seasons★
The condo was nicely stocked and had everything we needed for our family. Extra blankets in each closet and the beds were so comfortable! Easy to find and very close to the mountain we were skiing at for the week. Clubhouse with the pool was also within walking distance which was a huge plus.

White Mountains Ski and Golf Resort Home
Great spot! Clean. Bigger than you think. Easy to access just get off the highway!

Addie Shack in the White Mountains
Michael was fantastic with responding quickly, this home was beautiful & is a great location if you're looking to visit the white mountains! my friends & I had a great stay, we would definitely book again!

Hilltop View Lodge - White Mountains, NH
Our stay was wonderful at the cabin. The cabin was clean and centrally located to winter activities. Andrea was very responsive. Cant wait to go back again

Spectacular log home with private pool and hot tub
we had a great time at this house. very clean and comfortable! Definitely worth it! we would stay here again.

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

Large vacation home with a view
The house was amazing, the view off the back porch was gorgeous so many things to do around the house. Very responsive to questions, place was so clean looked exactly like how it was described. All around such an amazing experience can’t wait to go back!!
Quick stats about vacation rentals that are family-friendly in Madison
Total rentals
150 properties
Nightly prices starting at
G$6,294 GYD before taxes and fees
Total number of reviews
6.4K reviews
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
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- Sebago Lake
- Squam Lake
- Scarborough Beach
- Sunday River Resort
- Story Land
- Loon Mountain Resort
- Attitash Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Surfside Beach
- Franconia Notch State Park
- Fox Ridge Golf Club
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Cannon Mountain Ski Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Dartmouth Skiway
- Bald Peak Colony Club