Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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

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Guest favourite
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
4.82 out of 5 average rating, 125 reviews

Waterfront w/ Private Beach, Fire Pit & Canoe

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.

Top guest favourite
A large window offers a view of rolling mountains adorned with colorful autumn foliage. Shades of red, orange, and yellow contrast against the green trees, while a winding path is visible in the foreground, leading into the vibrant landscape.
Guest suite in Conway
4.98 out of 5 average rating, 621 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

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, 503 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
Condo in Bartlett
4.84 out of 5 average rating, 106 reviews

AttitashResort! 2-flr, 1-br, secure check-in

Location, Amenities, Convenience, All the things you're looking for in a perfect vacation get away! Enjoy every season at this well located mountain resort. Walk to all the Attitash Resort Activities like hiking, skiing, pools, hot-tubs and more all from this fully furnished condo 1 bedroom that sleeps 4 adults at the base of some of the best skiing in the east! Stay on the grounds or travel in any direction to create memories, relax, experience your best life. Fast Easy Reliable WIFI

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.
Guesthouse in Hiram
5 out of 5 average rating, 129 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!

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, 198 reviews

Ski Hideaway: XC from backyard, 15m to N. Conway

Clip into your XC skis at the back door or drive 15 mins to Cranmore. Casa Cedro is your ultimate winter basecamp. After the slopes, thaw out and plan your next adventure in our tranquil and cozy cedar cabin. High-speed internet keeps you connected, while the pine grove keeps you secluded. Our home is comfortable and modern without compromising the rustic White Mountain charm. 3 mins to Davis Pond for winter walks. A magical stay for couples & families seeking powder and peace.

Top guest favourite
Home in Eaton
4.97 out of 5 average rating, 332 reviews

White Mt Retreat: New Kitchen, W/D

Get away from it all in our lovely, spacious home with its new kitchen, in Eaton, only 15 min to the shops and restaurants in North Conway and five minutes to King Pine Ski Area. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home with two living areas is great for privacy and working remotely. Enjoy skiing at local peaks, hiking beautiful trails, warming in front of our fireplace or shopping in town. We are owner-operated

Guest favourite
The living area features high wooden ceilings and large windows, allowing natural light to fill the space. A comfortable couch is positioned near the windows, while a television is mounted on the opposite wall. The warm wooden flooring complements the rustic design.
Guesthouse in Brownfield
4.87 out of 5 average rating, 495 reviews

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

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, 107 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, 378 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 cottage exterior is surrounded by tall pine trees, providing a natural setting. A pathway leads to the front door, which is flanked by two small potted plants. The view of Pequawket Pond is visible in the background, enhancing the tranquil ambiance.
Cottage in Conway
4.96 out of 5 average rating, 197 reviews

Tiny Lakefront Cottage

Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.

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, 114 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 vacation rentals

When is the best time to visit Madison?

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Avg. price$308 CAD$328 CAD$272 CAD$267 CAD$287 CAD$310 CAD$350 CAD$342 CAD$299 CAD$329 CAD$312 CAD$350 CAD
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Frequently Asked Questions

  • 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.

  • 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 family-friendly chalet rentals in Madison?

    Madison has more than 10 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Madison with our chalet rentals, starting at about $120 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 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.

  • 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 Cabin Rentals in Madison?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 30 homes with a bbq area, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Madison

  • Total vacation rentals

    Explore 180 vacation rentals in Madison

  • Nightly prices starting at

    Madison vacation rentals start at $82 CAD per night before taxes and fees

  • Verified guest reviews

    Over 8,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    170 of Madison vacation 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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