
Holiday houses in Madison
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Madison
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison holiday rentals
Other great holiday rentals in Madison
Top Guest favourite

Home in Madison
4.88 out of 5 average rating, 34 reviewsBeautiful chalet home - walkable to beaches
KatherineRating, 5 stars1 month ago
Incredibly comfortable for 4 adults and 3 kids. The house was well stocked with kitchen staples and games for the kids. We loved walking to the pond and exploring the beach. Andy was so responsive and kind. Would definitely stay again!
Top Guest favourite

Home in Tamworth
5 out of 5 average rating, 16 reviewsKing Bed| Ensuite Bathroom|Playground|Game Area
InaRating, 5 stars3 months ago
We had a fantastic stay at Mark’s place! Everything is brand new, beautifully designed, and perfect for our ski getaway. The space was comfortable and well-equipped, making it easy to relax after a day on the slopes. It was also great for the kids, with plenty of room (including a game room in the basement) and thoughtful touches that made our stay even better. Highly recommend and would love to return!
Guest favourite

Guesthouse in Madison
4.91 out of 5 average rating, 11 reviewsQuiet Brookside Midweek Escape – Book Now & Save
DerekRating, 5 stars6 days ago
Lovely views. Comfortable bed. Spacious shower. Peaceful space. But: stairs! Mobility-challenged folks might find the steep staircase difficult, both up and down (as no handrail was available). Otherwise it is a lovely, comfortable, spacious, peaceful, thoughtfully prepared nest maintained by a welcoming host. We are thankful for wonderful accommodations reserved on short notice and would not hesitate to return — especially for a rematch of checkers! Thank you for having us.
Top Guest favourite

Chalet in Conway
4.98 out of 5 average rating, 48 reviewsCentral AC| Game RM| Fire Pit|Beaches Nearby
ChuckRating, 5 stars1 month ago
We stayed with friends, 3 couples, and there was plenty of room. Everything was clean and comfortable and there were some nice extra touches: some snacks waiting in the kitchen, extra toiletries in the bathrooms in case you forgot something, a basket of comfy blankets next to the "wood" stove for snuggling, a good supply of wood for the fire pit. We would definitely return if we get the chance.

Home in Madison
4.81 out of 5 average rating, 43 reviewsEidelweiss Boulder House
KeiraRating, 5 stars2 months ago
It was a great place to stay and the place matched the photos very well. Check-in and check-out were very easy and it’s a great location!!
Top Guest favourite

Cabin in Freedom
5 out of 5 average rating, 15 reviews3 bdrm + game room - Lake, Ski, Hike, Shop!
BobbieRating, 5 stars3 months ago
From the start, Ashley was helpful and kind. The house was immaculate and decorated tres chic, and she left a few treats to welcome us. Honestly, the place looked brand new! And it was so comfortable- the warm wood stove, the gourmet coffee ninja, the soft bedding and cotton sheets, the honeycomb wall shelves and little gold bumblebee towel holder….all the little touches were so special. Will definitely stay there again!
Guest favourite

Chalet in Madison
4.91 out of 5 average rating, 237 reviewsEidelweiss Chalet/1 min walk to pond/playground
JourdanRating, 5 stars6 days ago
The chalet was just as described. We were a little weary of the cleaning policy and Bill was great to explain why and how everything works. The house was clean when we arrived. It was perfect for an our family of 4, 2 kids and 2 adults. Small spaces in some rooms, but this didn’t bother us a whole lot. The playground and Little Pea Porridge Pond was sooooo accessible! Perfect for our family and the use of the kayak allowed us to venture into what we think was Middle Pea Porridge Pond. The neighborhood association does a good job at keeping the beaches and playground safe and clean. The brook was a wonderful feature, we were able to play in it several times and it was extra loud because of a rainy month and week leading up to our stay. Small, cozy spot tucked in the White Mountains.
Top Guest favourite

Home in Freedom
4.97 out of 5 average rating, 59 reviewsFarmhouse Retreat, Dog Friendly w/ Stunning View
MaryRating, 5 stars2 weeks ago
The house is gorgeous and the view is stunning. It was the perfect space for our family. We thoroughly enjoyed our stay. Definitely want to come back!
Quick stats about holiday rentals in Madison
Total rentals
170 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
6.9K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- China Holiday rentals
- Portland Holiday rentals
- Pocono Mountains Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- The Hamptons Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with lake access Madison
- House rentals Madison
- Rentals with a hot tub Madison
- Cabin rentals Madison
- Kid-friendly rentals Madison
- Rentals with a kayak Madison
- Rentals with a patio Madison
- Rentals with a fire pit Madison
- Pet-friendly rentals Madison
- Rentals with a fireplace Madison
- Rentals with outdoor seating Madison
- Rentals with a washing machine and dryer Madison
- Waterfront rentals Madison
- Chalet rentals Madison
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Dunegrass Golf Club