Holiday rentals in Madison

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Madison

  • Total holiday rentals

    Explore 170 holiday rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    160 of Madison holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Madison rentals

  • 4.9 Average rating

    Madison stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern chalet is nestled among trees, featuring a sloped metal roof and large windows. A deck with outdoor seating is visible, complemented by string lights. The gravel driveway leads to an inviting entrance, creating a serene outdoor setting surrounded by nature.
Chalet in Madison
4.98 out of 5 average rating, 44 reviews

Modern Chalet: 3BD/2BA Dog-Friendly|Kids Bunk

AUGUST DISCOUNTS-BOOK TODAY! SUMMER is here and the MOUNTAINS are CALLING! Make this MODERN CHALET your special getaway. This FAMILY and DOG friendly 3 BD/2 BA home is located in the heart of Eidelweiss with a view of the water! Fully stocked kitchen and comfortable living space w/kids wildlife bunk room, outdoor shower, fire-pit and more! If you are looking for a relaxing getaway kayaking on the lake or exploring the mountain peaks, make this mountain chalet your summer escape in the WHITE’s!

Top guest favourite
A serene view of Silver Lake is presented, with gentle waves visible in the distance. A private dock extends into the water, framed by lush green trees. Two canoes rest on the sandy ground nearby, adding to the tranquil lakeside scene.
Cabin in Madison
4.95 out of 5 average rating, 56 reviews

2 bedroom lake view cabin with private dock and AC

Welcome to Squirrel Patch, a cozy cabin next to the beautiful Silver Lake. Enjoy our private lakeside access with private dock and canoe, or walk along the abandoned railroad tracks to one of many nearby beaches. You can even harvest the wild blueberries that grow abundantly in the fall. This cabin has central AC/heat, a screened porch, full kitchen, outdoor grill and fire pit, and a cozy living room with a futon that can be used as an additional bed if needed! The dock is removed on Oct 1st.

Guest favourite
A spacious game room is featured, showcasing a pool table, a new ping pong table, and a foosball table. Comfortable seating is provided with a patterned couch, and natural light enters through several windows, illuminating the enjoyable game area.
Home in Madison
4.82 out of 5 average rating, 127 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.

Top guest favourite
A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.
Guest house in Hiram
5 out of 5 average rating, 134 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Top guest favourite
Flat in Madison
4.97 out of 5 average rating, 64 reviews

Silver Lake access from yard | Birding Hot Spot

I'm going to let our guest describe it... "Perfect location steps away from Silver Lake. Between the lake district and the White Mountains, Madison allows you access to both without the crowds." "One of the best Airbnbs I’ve stayed at. Such a large upper apartment with a beautiful backyard overlooking the field and stream. Felt great to be in. Quiet. Peaceful." "This place is like a hidden gem! Spacious accommodations, soft sheets, a beautiful view, and Jen was an amazing host."

Guest favourite
A modern cabin exterior is surrounded by lush greenery, featuring a spacious outdoor area with a fire pit at the center. Four wooden chairs are arranged around the fire pit, while a picnic table is nearby. String lights are hung to enhance evening ambiance.
Cabin in Madison
4.93 out of 5 average rating, 215 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.

Top guest favourite
A fire pit area is surrounded by several blue Adirondack chairs, arranged in a circle on a ground covered with natural earth. A hammock hangs between two trees, while string lights provide a soft glow overhead, creating an inviting space for gathering.
Home in Madison
4.98 out of 5 average rating, 174 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..

Top guest favourite
Home in Madison
4.97 out of 5 average rating, 29 reviews

Redwood Retreat | Lake Access | Mtn. Getaway

Tucked away in the woods of Madison, NH, this 3BR, 2BA retreat is your launchpad for adventure and relaxation. Enjoy lake access for swimming or paddling, explore scenic hiking trails, then unwind by the cozy gas fireplace or gather ‘round the crackling fire pit under starry skies. With 2 luxurious king beds, modern amenities, and plenty of space to stretch out, this serene hideaway offers the perfect blend of comfort and wilderness. Book now and make memories that last!

Superhost
Chalet in Madison
4.81 out of 5 average rating, 146 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.

Top guest favourite
Cabin in Madison
4.98 out of 5 average rating, 109 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.

Top guest favourite
Chalet in Madison
4.92 out of 5 average rating, 258 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.

Top guest favourite
The loft area displays warm wooden paneling and a prominent stone chimney. A red couch is placed near a patterned area rug, while several windows allow natural light to fill the space. An open railing separates the loft from the main level, adding to the spacious feel.
Cabin in Madison
5 out of 5 average rating, 117 reviews

Cozy & Charming Custom Log Home in Madison

Unwind in our cozy custom log home, newly crafted with all the amenities! Featuring a gorgeous stone chimney, open floor plan, covered porch, and large deck. Minutes from North Conway shopping, skiing, trails, rivers, and lakes. Located on 113 in Madison. In the winter, snowmobile or snowshoe from the cabin! Very clean, tidy, and stocked with necessities. Relax and enjoy all our beautiful area has to offer.

Popular amenities for Madison holiday rentals

When is the best time to visit Madison?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$335 SGD$355 SGD$292 SGD$252 SGD$271 SGD$293 SGD$331 SGD$323 SGD$283 SGD$311 SGD$295 SGD$331 SGD
Avg. temp-15°C-14°C-11°C-5°C2°C8°C10°C9°C6°C0°C-6°C-11°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Madison?

    Four-legged friends are welcome in Madison. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Madison?

    Yes! Work meets play with ease at over 70 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly cabin rentals in Madison?

    Madison has more than 20 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Madison?

    Experience the best of Madison with our cabin rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Madison have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Madison have wifi?

    Absolutely! We offer over 110 house rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Madison have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Chalet Rentals in Madison?

    Enhance your stay in our Chalet Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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