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 favorite
An indoor fireplace stands against a light-colored brick wall, complemented by decorative pampas grass in a vase. A cozy seating area features plush cushions, while a spacious sleeping area is visible in the background with a king-size bed and ample natural light from large windows.
Chalet in Intervale
4.83 out of 5 average rating, 240 reviews

Cozy 1 Bed Chalet w/ King Bed & Indoor Fireplace

Cozy up at this unique and tranquil getaway cabin. Perfectly set up for 2 people, this charming A-frame is spacious, peaceful and well thought out. If its a romantic getaway you are looking for, look no further!! - with the king four-poster bed, the indoor fireplace & large, private back deck with grill you will have everything you need to enjoy & relax during your stay in the White Mountains. Close enough to everything to be convenient yet far enough away from it all for privacy and peace!

Guest favorite
The living area features wooden walls and a cozy sofa accented with colorful pillows. A lighted table sits beside a small lamp. The kitchen is visible in the background, showcasing modern fixtures and glassware.
Cabin in Conway
4.92 out of 5 average rating, 390 reviews

N. Conway…Cozy Cabin, Centrally Located

Our newly renovated cabin is family friendly (childproofed), stylish, and cozy with lovely wooden accents throughout! It is newly furnished and has brand new mattresses! This cabin is wonderfully located just off of Westside Rd. a mere skip away from Echo Lake, Cathedral Ledge, Diana's Baths etc...It is a 5 - 8 minute drive to North Conway Village and Cranmore Ski Resort; and a 5 - 8 minute drive from Settler's Green Outlets, grocery stores etc...with numerous other popular destinations nearby.

Guest favorite
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, 496 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 favorite
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, 195 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 favorite
A dining area features a small round table and two wooden chairs, positioned by large arched windows. Natural light floods the space, illuminating plants on the table. A vintage ski-themed poster decorates the wall, complementing the serene wooded views outside.
Apartment in Jackson
4.97 out of 5 average rating, 594 reviews

Studio, pet friendly, river views, Jackson NH

Sunny studio with king bed, private entrance, garage parking. Small but complete kitchen (under counter refrigerator). Great views of the Wildcat river. WiFi, cable. 1 mile to Jackson cross country trails and close to the village of Jackson. Non smoking. The space is 500 square feet. There is a two night minimum stay. Pet friendly. Starting in 2025, we will allow 1 dog without charge. You will be charged $40/stay for a second dog. Please supply information on breed and size.

Guest favorite
The exterior of the cabin is highlighted by its warm red wood siding, featuring a large paneled door and adjacent picture window. A tranquil natural setting surrounds the cabin, with green grass and trees creating a serene atmosphere.
Home in Sugar Hill
4.87 out of 5 average rating, 365 reviews

Cozy guest house near Littleton and Cannon Mtn

This rustic north country cabin offers 2 bedrooms and 1 bath for up to 4 guests. It has been renovated with comfortable beds and pillows, new appliances, a toasty pellet stove, a beautiful 75" TV with soundbar and subwoofer for movie nights, ample parking. It's located 9 minutes south of downtown Littleton and 11 minutes north of Cannon Mountain. Whether you're visiting for winter sports, leaf watching, mountaineering, or Polly's Pancakes, we're close to the action.

Top guest favorite
A cozy cabin interior features warm wooden walls and flooring. Twinkling string lights adorn the ceiling, creating a soft glow. A comfortable armchair is positioned beside a small lamp, with a spacious bed visible in the background, framed by large windows allowing natural light.
Cabin in Lovell
4.97 out of 5 average rating, 401 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

Top guest favorite
A charming cabin is nestled among snow-covered trees, with a stone chimney and wooden exterior. Stepping stones lead to a welcoming entrance, where a large window offers natural light. The surrounding landscape features a gentle snowfall, enhancing the peaceful, wooded setting.
Cabin in Intervale
4.94 out of 5 average rating, 353 reviews

Private Cabin on 1.7 acres w/ Fireplace White Mtns

Escape to your own peaceful corner of the White Mountains at Grizzly Cabin - an intimate, dog-friendly retreat tucked on nearly 2 wooded acres. Perfect for couples, solo adventurers, and nature lovers, this cozy cabin offers a rare combination of privacy and convenience. Just minutes from the charm of North Conway and a short drive to world-class ski slopes and hiking trails, it's the ideal home base for all your White Mountains adventures!

Top guest favorite
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 favorite
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, 369 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.

Guest favorite
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, 191 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 favorite
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.

Popular amenities for Madison vacation rentals

When is the best time to visit Madison?

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Avg. priceG$47,051 GYDG$50,188 GYDG$41,614 GYDG$40,778 GYDG$43,914 GYDG$47,469 GYDG$53,534 GYDG$52,279 GYDG$45,796 GYDG$50,397 GYDG$43,496 GYDG$49,561 GYD
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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 cabin rentals in Madison have wifi?

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

  • Are there family-friendly house rentals in Madison?

    Madison has more than 100 family-friendly house 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 $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do chalet rentals in Madison have air conditioning?

    Absolutely! We offer over 10 chalet rentals with air conditioning 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 House Rentals in Madison?

    Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with wifi, over 60 homes with a bbq area, over 90 homes with air conditioning, 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 G$12,547 GYD 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 & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Madison vacation rentals include wi-fi 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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