Vacation rentals in Madison

4.97 out of 5 average rating, 114 reviews

A wooden walkway leads to the entrance of a chalet, framed by trees displaying fall colors. The mountain scenery in the background reveals rolling hills under a partly cloudy sky, enhancing the sense of elevation and connection with nature.

Chalet in Madison

Breathtaking mountain views - Hidden gem!

Chalet in the Clouds!⛅️ Relax & Rejuvenate w/ panoramic views of White Mountains from any of the 4 decks of Kailaśa Chalet! Perched on top of a mountain overlooking Mt Chocorua & Silver Lake w/ majestic views of Mt Washington Valley. So easy to get lost in the beauty of Kailaśa! Wake up to the experience of being above the clouds overlooking the valley! Settle down after dinner around the stone fireplace while watching your favorite shows on 65" TV It's not just a rental it's an experience!

4.93 out of 5 average rating, 44 reviews

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

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.

4.97 out of 5 average rating, 318 reviews

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

Airbnb Award Winning Home :New Kitchen, Beach Pass

Get away from it all in our lovely, spacious home with its new kitchen, in Eaton Center, just 5 minutes to Crystal Lake and the Eaton Village store/cafe, and 15 min to the shops and restaurants in North Conway. 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

4.84 out of 5 average rating, 102 reviews

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

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.

4.94 out of 5 average rating, 176 reviews

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

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.

4.95 out of 5 average rating, 120 reviews

The exterior of the house features a combination of timber frame siding with a light-colored front and dark wood accents. A grassy area is present, surrounded by lush greenery and orange flowers. A hammock is seen in the yard, creating a peaceful outdoor space.

Cottage in Tamworth

5*Clean! *Private patio *Sleeps 6 *Outdoor Shower!

This home has many unique areas to unwind inside & out! *Private sunken patio fully equipped with a LP/charcoal grill *Firepit *Covered outside dining *Lounge chairs *2-Hammocks *OUTDOOR SHOWER! *Sunporch *Private driveway *Quiet tucked away yard surrounded by nature! *Close to many Hikes & Wedding venues. 'The Corner House', a timber frame cape, is perfect for a New England getaway. The house consists of a re-located1820's post & beam frame and is great place to gather with family & friends

4.83 out of 5 average rating, 458 reviews

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

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!

4.95 out of 5 average rating, 163 reviews

A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.

Cabin in Conway

The Conscious Cabin

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

4.99 out of 5 average rating, 253 reviews

A cozy cottage is framed by lush greenery and colorful landscaping, featuring a welcoming front porch and a sunroom with large windows. A picnic table is positioned nearby, inviting outdoor relaxation. The property is set against a backdrop of trees, contributing to a private and serene environment.

Cottage in Brownfield

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

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.

4.97 out of 5 average rating, 152 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.

4.95 out of 5 average rating, 354 reviews

A charming cottage is nestled among tall pine trees, with a black metal roof. It features a welcoming front porch and a natural wood pathway that leads to the water's edge. The serene pond is visible beyond the cottage, framed by lush greenery.

Cottage in Conway

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!

4.91 out of 5 average rating, 77 reviews

The cabin features a metal exterior with large windows and a visible American flag hanging from the side. A wooden deck extends in front, surrounded by lush greenery, and a serene pond is seen in the background, providing a calm and natural environment.

Cabin in Madison

Lakeside camp near North Conway

Lakeside cabin near the White mountains! 2/1 updated cabin with stunning views of Davis Pond. 2nd cabin available if you need more room or need space for two families! Snowboarding,Skiing, hiking, snowmobiling, or Swimming, fishing, paddle boarding! No motors allowed on our lake. It is a peaceful retreat from your busy life. The deck has a propane fire table and downstairs we have place for bonfires and roasting smores!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Madison vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Madison

4.91 out of 5 average rating, 33 reviews

A scenic view of the river framed by lush greenery, with trees lining the banks. A vibrant rainbow arches across the sky, adding color to the serene landscape. Water flows gently, reflecting the natural setting.

Home in Conway

Rivers View

A three-level home is surrounded by lush greenery, featuring large windows that invite natural light. A spacious wrap-around deck showcases outdoor seating, with a pathway leading through landscaped gardens in front of the house. Solar panels are visible on the rooftop.

4.97 out of 5 average rating, 34 reviews

Secluded cozy family retreat, dog friendly!

A welcoming living area features wooden beams and a warm color palette. A comfortable sofa and armchairs are arranged around a wooden coffee table, with a cozy stove and a television visible in the background. Natural light streams through the windows, enhancing the cabin's rustic charm.

4.85 out of 5 average rating, 55 reviews

Mountain View | Ski Town | Fireplace |Hiking Trail

A charming alpine-style cabin is set against a snowy landscape, showcasing a steep staircase leading to the entrance. Large windows allow for ample natural light, framed by dark wood and green accents. Tall trees surround the home, enhancing its secluded feel.

4.81 out of 5 average rating, 43 reviews

Eidelweiss Boulder House

The exterior of a modern home is presented, featuring large windows and a striking red façade. A spacious deck extends from the house, equipped with outdoor seating and a canopy. Surrounded by lush trees, the setting offers a natural, tranquil atmosphere during a soft sunset.

4.81 out of 5 average rating, 21 reviews

StoneWood Lodge | Lake Access | Arcade Room | Yard

A hot tub is invitingly filled with bubbles, surrounded by lush green trees. A cocktail sits on the ledge, adding a touch of relaxation to the serene outdoor setting.

4.97 out of 5 average rating, 34 reviews

Close to Lake|Htub|Game Rm|FirePit|Stunning Design

5 out of 5 average rating, 27 reviews

The exterior of a newly built house is depicted, featuring a striking blue vinyl siding and a covered front porch. A wooden step leads to a double door entrance, framed by a landscaped yard and trees, creating a peaceful setting.

Home in Albany

Newly Built House Near the Kanc!