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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Top guest favourite
A serene lakeside view features numerous boats anchored in calm water, surrounded by distant mountains. A sandy beach extends along the shoreline, leading to a wooden pier. The sky is clear, emphasizing the tranquility of the natural landscape.
Home in Freedom
4.98 out of 5 average rating, 115 reviews

Perfect Family Getaway On Lake Ossipee

Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

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
4.83 out of 5 average rating, 127 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
An open-concept living space features high cathedral ceilings with wooden beams. A cozy seating area with a sectional sofa faces a contemporary gas fireplace. A well-appointed kitchen with an island and stainless-steel appliances is adjacent to the dining area, where natural light floods in from multiple windows.
Home in Conway
4.98 out of 5 average rating, 166 reviews

Riverfront Getaway in Conway, Saco River Farmhouse

Welcome to The Saco River Farmhouse! This newly renovated riverfront retreat has everything for a perfect White Mountains getaway. Just 10 minutes from North Conway’s restaurants, shops, and outlets. The open layout offers a spacious, inviting atmosphere for relaxing with loved ones. In summer, float from your private Saco River access or relax on the back deck. In winter, you're minutes from ski resorts and snowmobile trails. In the fall, enjoy breathtaking foliage and crisp mountain air!

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, 126 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
The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.
Home in Naples
4.99 out of 5 average rating, 175 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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

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, 170 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
The exterior of the house features a rustic red wood siding with large windows, set within a lush green landscape. The sloped roof is adorned with a bright red metal covering, complementing the natural surroundings. Smooth stones lead up to the entryway, surrounded by carefully maintained grass and shrubs.
Home in Eaton
4.97 out of 5 average rating, 334 reviews

White Mt Retreat w/ Beach Pass, 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

Top guest favourite
A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.
Home in Bridgton
4.98 out of 5 average rating, 164 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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, 381 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 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, 115 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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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 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 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 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 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 90 homes with air conditioning, over 100 homes with wifi, over 60 homes with a bbq area, 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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