
Chalet vacation rentals in Madison
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Top-rated chalet rentals in Madison
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Popular amenities for Madison chalet rentals
Family-friendly chalet rentals

Lake Side Lodge
Beautiful quaint area on a lake to get away from the noise. Great for family retreats.

7 mins to Storyland! Dog friendly!
Cozy, clean place. Great location for ski in/out. Attitash Abenaki lift is just right next to back yard. Owner communication is excellent. We had wonderful time with kids during our ski trip! Thanks Donald.

Lake Ossipee Village, Freedom, NH
I recently had the pleasure of staying at this delightful cabin nestled in the woods of New Hampshire, and it was an experience I won’t soon forget. From the moment I arrived, I was enchanted by the serene surroundings and the cozy ambiance of the cabin. The cabin itself is beautifully maintained and exudes rustic charm. Inside, the space is warm and inviting, with thoughtful touches that make it feel like a home away from home. The living area is perfect for relaxing after a day of exploring, with a super comfortable couch. The kitchen is well-equipped with everything you might need to prepare meals. One of the best features of this cabin is its location. It’s perfectly secluded, offering privacy and a true sense of escape. I spent my mornings sipping coffee on the porch, watching the wildlife.

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!!

Eidelweiss Chalet/1 min walk to pond/playground
We had a great winter stay at the chalet! It’s a cozy and comfortable home overlooking a stream, in a convenient location to much of the White Mountains region. And a good price in exchange for bringing your own linens and cleaning up after yourself—William is very responsive and provides clear instructions about what supplies you’ll need to bring and what cleaning is expected.

Charming Jackson Cabin • Great View & location
The host was so kind and responsive! The location is perfect- so close to North Conway but not right in the middle where there's more traffic. Not far from Storyland. Beautiful scenery, quiet neighbors. The house was very clean and cozy. Perfect for my husband and I. Host was very accommodating to bringing my two large dogs.

Family Chalet Near Story Land | Private Hot Tub!
We love Jeremiah and Lisseth’s place! It was a great stay. We really appreciated how clean the house was and how well they communicated with us. It was a comfortable environment and we felt right at home. The fire place and hot tub were big perks for our group. They made sure we had everything we needed and showed they care. We will definitely book a stay with them in the future!

Spacious, air-conditioned condo next to Storyland!
Very peaceful place, spacious and well maintained. Looking forward to a nonrainy stay in our future!
Luxury chalet rentals

Pine Brook Lodge, 9 br, 5 ba, game room, fireplace
We have worked with Katie in the past and were super impressed with how helpful she was. We loved this house! The game room was perfect for our large group. The young children enjoyed hanging out in the cute playroom upstairs. It was so helpful to have a crib and high chair available. The large front lawn was perfect for our field day games. We hope to be back next year if the family can get schedules all set 😁

6 BR | EV Charger | No Pet Fee | Pool Table
Samuel's place was better than what we hoped for. We were there with 4 couples for my son's wedding. I've been in Airbnbs around the world and this is the only one that provided extras like coffee, sugar, spices, olive oil, aluminum foil, paper plates & napkins. It may seem like a small thing but it really makes a difference when traveling. Extras like the towels displayed in decorative styles were another nice finishing touch. All my guests were impressed. The house was pristine in every way. Thank you so much for such a memorable stay!

5BR/2BA-Grill| Game Rm| 5 Beaches Nearby| Fire pit
We absolutely love this place. We stayed there years ago for a softball tournament and my son was dying to bring his cousins, especially to play the Ninja Turtles arcade game in the game room. It was perfect. The kitchen is really well stocked, which was SO helpful with a big group - we cooked breakfast and dinner each night for everyone. It's really close to a ton of great things to do in the area. Hosts were wonderful.

Mt. Wash views 3 floors bed/bath on each floor
We had such a wonderful time! Exactly what Katie stated. Katie was very quick to response to any questions we had. Very private, quiet and close to town. The view was spectacular. Snow on the White Mountain Caps in May. Beautiful!!! Will give this Chalet a 110 percent and would definitely book again. Thank you Katie for a wonderful stay! Sharon and Bob plus 2.

Winnepesaukee/Gunstock/Bank of NH Pavilion Chalet
The stay was fantastic. The hosts were great. So proactive with information and always responsive! The house was beautiful, in such a great location and perfect for what we needed. Next year we will definitely be looking into this house again.

The Moose Chalet- Walk to Diana's Baths!
The Moose Cabin is a *very* wonderful place to stay: * very spacious and perfect for multiple families / friends to hang out together * perfect for toddlers / kids - even has tons of kid stuff like crib, toddler bed, toys, highchair * clean and clutter free * comfortable beds and couches * fully stocked kitchen for cooking...all the standard stuff you may need as well as extra things like instantpot * quiet, scenic neighborhood in perfect location for so many NH daytrips while also having easy access to North Conway grocery stores / restaurants * nice outdoor deck for sitting outside We stayed for a week with extended family. Beyond the weather being unseasonably cold / rainy and hampering some of our hiking plans we couldn't have asked for a better trip.

Hot Tub, Lakefront Access, Fire Pit, Free Firewood
This house was amazing. Everything was built so well in the house, plenty of room for us to spread out, and lots to do at the house, which was helpful for us with our rainy weekend. We said that we will have to come back and stay again in the winter to go skiing.

Mountain View Chalet
Great location! Property came exactly as advertised. Justine was super attentive with communication. The chalet is well laid out and easily accommodated our group. Everything was well thought out from the wi-fi, to the kitchen and beyond. When we arrived someone actually had firewood perfectly stacked in the pit so all we had to do was light a match and presto, mountainside camp fire and smores! Nice touch Justine! Can't emphasize enough how great the location is. North Conway and all of the shops and dining that go with it is 5 minutes away and for the outdoorsy there are an abundance of hiking and mountain biking trails equally as close.
Lakefront chalet rentals

On Lake Christopher, Close to Sunday River
Nova’s place is so spacious and peaceful. Everything looked great and was cozy and accommodating. Fall on the lake is amazing!

Charming & Cozy 3 Bedroom Chalet
Great HQ for a long weekend of hiking. Pricing was reasonable. Chris was very helpful and responsive (including checking in to make sure everything was up to our standards). Would stay here again. Location was amazing.

Waterfront Getaway - Fishing, Canoeing, & Skiing
We had a fantastic stay as a group of four adults and two kids. Jason was an excellent host—he responded within minutes and was incredibly helpful with anything we needed. The kitchen was very well stocked, with appliances that seemed brand new. There were plenty of toys and games to keep the kids entertained. We loved the brand new Weber gas grill, which we used every day. The fireplace was well supplied with wood, adding a cozy touch. The lake is absolutely beautiful and surrounded by nature—we even spotted a deer!

Mountain cabin with views, privacy, and more.
Great place to stay for a relaxing weekend! Beautiful views and the Airbnb had everything we needed. Pots & pans were a little hard to use - not very non-stick - so might recommend bringing your own if you plan to cook a lot. Everything was comfortable though and clean when we arrived!

The Chalet - Waterfront Home on Quiet Crystal Lake
We love our weekend at house. Everything it’s great!!! Thank you John!!!

The Chalet~ 4 bed Lakefront Family Vacation
Incredible views of the lake, we had a great stay
Quick stats about chalet rentals in Madison
Total rentals
20 properties
Nightly prices starting at
G$27,276 GYD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Sebago Lake
- Squam Lake
- Scarborough Beach
- Sunday River Resort
- Loon Mountain Resort
- Story Land
- Attitash Mountain Resort
- Weirs Beach
- Surfside Beach
- Owl's Nest Resort
- Franconia Notch State Park
- Fox Ridge Golf Club
- Cranmore Mountain Resort
- Mount Washington Cog Railway
- East End Beach
- Palace Playland
- Purity Spring Resort
- King Pine Ski Area
- Cannon Mountain Ski Resort
- Parsons Beach
- Bald Peak Colony Club
- Diana's Baths
- Ferry Beach
- Cliff House Beach