Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Superhost
A relaxed outdoor area features wooden Adirondack chairs arranged around a fire pit, with smooth stones providing a natural border. A kayak rests on the sandy shore next to the calm water, while a charming two-story chalet is visible in the background, surrounded by trees.
Chalet in Madison
4.83 out of 5 average rating, 115 reviews

White Mtns Waterfront Chalet w/ Private Beach

This charming chalet is nestled on the edge of Little Pea Porridge Pond in the enchanting village of Eidelweiss, an alpine oasis just a short drive from Mt Washington Valley. Enjoy campfires on a private sandy beach; Fishing, swimming and boating in the warmer months; Snowmobiling, skiing and ice-skating in the Winter season. Nearby attractions incl. King Pine, Cranmore and Attitash Ski Resorts; N Conway Village; Kancamaugus Highway, Hiking Trials, Waterfalls, shopping and gourmet restaurants.

Superhost
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, 191 reviews

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.

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
4.83 out of 5 average rating, 118 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.

Guest favourite
A compact kitchen area is shown, featuring a full-size refrigerator, stove, and sink with countertop space. Cabinets are installed above and below the counter. A cozy futon couch is positioned in the foreground, complementing the warm wooden paneling on the walls.
Home in Albany
4.83 out of 5 average rating, 489 reviews

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!

Guest favourite
A serene outdoor space features a fire pit surrounded by natural stone. Lush greenery extends to distant mountain views under a partly cloudy sky, creating a peaceful setting for relaxation and outdoor gatherings.
Cabin in Tamworth
4.9 out of 5 average rating, 535 reviews

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

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, 123 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
The two-story mountaintop home is framed by lush greenery and features a spacious deck with a red umbrella. Stacked firewood is neatly arranged under the deck, and large windows allow natural light to illuminate the interior.
Home in Madison
4.97 out of 5 average rating, 159 reviews

Beautiful Getaway Chalet - Mountain Views!

Private mountaintop home! My home is located in the beautiful community of Eidelweiss with private beaches, swimming, and a playground. Located minutes from North Conway and close to all Mount Washington Valley ski areas, activities, and tax-free shopping. Just a two-hour drive from Boston and you're ready to experience crystal clear rivers, pristine lakes, covered bridges, majestic mountains, picturesque hiking, and numerous local attractions and parks.

Top guest favourite
A charming log cabin is surrounded by lush greenery and tall trees. The building features a welcoming front porch with steps leading up to the entrance. Flowering shrubs and a well-maintained garden area enhance the cabin's natural setting.
Cabin in Madison
4.98 out of 5 average rating, 106 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
The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.
Guest suite in Conway
5 out of 5 average rating, 358 reviews

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.

Top guest favourite
The cabin is nestled in a snowy landscape, featuring a sloped roof and large front windows. A wooden deck runs along the front, surrounded by tall, snow-covered trees. The ground is blanketed in thick snow, creating a serene winter atmosphere.
Flat in Conway/Albany
4.96 out of 5 average rating, 252 reviews

Dog friendly, lower level apartment off the "Kanc"

The cabin is located off Kancamagus Hwy, one of the most scenic roads in the US. The outdoor activities are endless, from hiking, biking, snowshoeing, alpine/x country skiing , golfing, horseback riding and tons of shopping at the infamous "outlet stores" You’ll love the cabin because of it's rustic motif, quiet neighborhood, and fresh mountain air. The cabin is good for couples, solo adventurers, biz travelers, and furry friends .

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, 109 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.

Guest favourite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield
4.96 out of 5 average rating, 245 reviews

Riverfront cabin between Portland & White Mtns.

Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Popular amenities for Madison holiday rentals

When is the best time to visit Madison?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$293 SGD$312 SGD$259 SGD$254 SGD$273 SGD$295 SGD$333 SGD$325 SGD$285 SGD$314 SGD$271 SGD$308 SGD
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Frequently Asked Questions

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

    Yes! Work meets play with ease at over 90 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Madison?

    Four-legged friends are welcome in Madison. Choose from more than 90 vacation rentals for guests traveling with pets.

  • Do chalet rentals in Madison have wifi?

    Absolutely! We offer over 10 chalet rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

  • 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 cabin rentals in Madison have air conditioning?

    Absolutely! We offer over 20 cabin rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Madison have a bbq area?

    Absolutely! We offer over 30 cabin rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 100 homes with wifi, over 90 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Madison

  • Total holiday rentals

    Explore 180 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 7,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    160 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    170 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!

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