Madison vacation rentals

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

4.83 out of 5 average rating, 114 reviews

A welcoming cabin is situated down a gravel driveway surrounded by tall trees. Warm light spills from the windows, creating a cozy ambiance as dusk settles. A lantern beside the pathway adds a gentle glow, inviting guests toward the entrance.

Home in Conway

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

Townhouse in Bretton Woods

Two blue armchairs are positioned in front of large windows, offering views of the surrounding landscape. Natural light floods the room, highlighting the wooden floors and modern decor. Soft curtains frame the windows, creating a cozy atmosphere.

4.86 out of 5 average rating, 59 reviews

CR11 Top Rated Ski-In/Out with views, AC, Pool/gym

Popular 3-level townhouse in upscale Crawford Ridge development. No need to drive to hit the slopes, and enjoy fireplaces and views of Mt. Washington. 2 living areas, AC, modern amenities, and close to attractions. Open kitchen, dining, and living room with stone fireplace. Primary bedroom with electric fireplace and ensuite bathroom. 2 additional bedrooms and shared bathroom upstairs. Lower level with second living room, 2 bedrooms, and shared bathroom. Central location for outdoor adventures!

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.91 out of 5 average rating, 93 reviews

A spacious sunroom features large windows allowing natural light to fill the area. Comfortable seating is arranged against the wall, complemented by a decorative coffee table. Greenery and street views are visible through the windows, creating a serene atmosphere.

Home in Conway

Downtown North Conway– private pool & hot tub!

How would you like to set up base in the heart of North Conway Village with a private pool!? (hot tub arrives in June) This prime location is minutes from Zeb's General Store, Peaches, Horse Feathers, and the Conway Scenic Railroad, so you'll be close to all the action in the village. Conveniently located off North South Road, 2 minute drive to Cranmore, or just minutes for a day of shopping at Settlers Green. Perfect for enjoying everything the White Mountains and North Conway have to offer!

4.94 out of 5 average rating, 161 reviews

The exterior of a spacious mountain townhome is captured, featuring a warm wood façade and large windows that allow natural light inside. A deck extends from the front, overlooking a snowy landscape, with tall trees framing the serene setting.

Home in Carroll

Cozy Townhouse: Bretton Woods Mt. Washington Place

In the Mount Washington Resort (Bretton Woods) and near Cannon Mountain. Inviting four-season end-unit town home with warm ambiance, all the comforts you need, and great views. A mountain vacation getaway at a great value. Modern kitchen, comfortable dining and living room with fireplace. Four bedrooms, three floors, each with private bathroom (three full, one with shower). Large entertainment / recreation room for the family, outside deck with seating to enjoy the wildlife and a grill.

4.96 out of 5 average rating, 160 reviews

A stone fireplace with a modern design is centered against a rustic wall, featuring stacked firewood on either side. The warm glow of the fire illuminates the surrounding area, complemented by natural wood beams on the ceiling.

Condo in Lincoln

Gorgeous River & Loon Mountain View Studio Condo

Cozy Studio Condo in hotel resort community sleeps 3. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy Lovely views of the mountain and Pemi River! You'll love the nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

4.98 out of 5 average rating, 54 reviews

A fire pit surrounded by four wooden Adirondack chairs is set against a gravel area. The rustic lodge can be seen in the background, framed by trees displaying autumn colors and string lights. A peaceful and inviting outdoor space is highlighted.

Home in Jackson

The Sommet-Magical Views- Main house+Guest cottage

Welcome to The Sommet in Jackson, NH – a mountain getaway lodge - MAIN HOUSE with a GUEST COTTAGE. Picturesque views, local restaurants, and endless recreation await you at this 3-bedroom, 3-bath vacation rental! Located within minutes of Mt Washington, and the multiple ski areas. Mountain biking and hiking locations within minutes’ drive. Saco River provides outdoor recreation like canoeing, kayaking, tubing and rafting. Swimming, fishing could make this a perfect summer getaway.

4.85 out of 5 average rating, 350 reviews

A natural rock formation features small waterfalls cascading into a clear pool. Surrounding greenery adds a touch of nature, while guests are seen enjoying the water. Sunlight reflects off the rocks, creating a warm atmosphere.

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

PLEASE DO NOT BOOK PEAK HOLIDAYS/WEEKENDS IN ADVANCE as we try to rent the entire house 1st. We book this listing as a 1 bedroom ONLY. Directly in the village! yet tucked away, private YARD, HOT TUB, fireplace, new furniture, cozy beds and & linens. WALK to restaurants, Saco River, Golf, Village Green, Rec Center, Whitaker Woods, scenic train station, coffee shops, stores, skating, Cranmore & nightlife. Enjoy Kayaking, skiing, adventure parks, skiing, story land, hiking, etc.

4.96 out of 5 average rating, 78 reviews

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

4.93 out of 5 average rating, 352 reviews

A serene river flows through rugged granite formations, surrounded by vibrant autumn foliage. Tall trees flank the banks, showcasing a mix of greens, yellows, and oranges. The distant mountains rise gently under a clear sky, creating a tranquil natural landscape.

Condo in Lincoln

Cute Studio Apt Resort Lincoln, NH Loon Mountain

Quaint Studio Apartment, Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Skiers & snowboarders enjoy the Free Shuttle to Loon Mountain Ski Resort only minutes away. Great area dining, and outdoor activities, indoor pool, outdoor pool, Sauna, Jacuzzi and game room make this is a great vacation location for your family. Great restaurants within walking distance.

4.98 out of 5 average rating, 87 reviews

A spacious lawn is surrounded by trees, providing a serene backdrop for outdoor activities. Comfortable seating is arranged near a firepit, while a rustic barn stands in the distance. A well-maintained walkway leads to the entrance of the charming red house.

Cottage in Hill

The red house

Charming Country Retreat in Hill, NH - Perfect for Families and Groups Welcome to our serene home in the charming town of Hill, New Hampshire! Nestled on 12 scenic acres, this inviting home offers the perfect blend of tranquility and adventure for families and groups looking to escape the hustle and bustle. Feel free to reach out if you have any questions or need additional information. We’re here to help make your stay perfect!

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

Stay near Madison's top sights

King Pine Ski Area104 locals recommend

Hobbs Tavern & Brewing Company68 locals recommend

White Lake State Park34 locals recommend

Almost There Restaurant20 locals recommend

Rosie's Restaurant19 locals recommend

White Lake Speedway17 locals recommend

Other great vacation rentals in Madison

4.99 out of 5 average rating, 68 reviews

An inviting exterior view of the property showcases a red house surrounded by lush greenery. String lights illuminate the outdoor seating area, which includes comfortable chairs and a hot tub, creating a serene atmosphere for relaxation.

Home in Thornton

70 Acre White Mountain Estate – Panoramic Views

4.93 out of 5 average rating, 58 reviews

A modern kitchen is highlighted with sleek white cabinets and a polished granite countertop. High-end stainless steel appliances, including a gas range, are featured. The open layout connects to a bright living area, where natural light fills the space through large windows.

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

5 out of 5 average rating, 22 reviews

Apartment in Bartlett

Large Family Apartment

4.92 out of 5 average rating, 179 reviews

A charming log cabin with a gabled roof is set against a clear blue sky. Large windows enhance the natural light and provide views of the surrounding trees. A spacious deck features outdoor seating, surrounded by stone steps leading to the lush green yard.

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping

4.85 out of 5 average rating, 105 reviews

A spacious living area features a large sectional sofa, a coffee table, and a flat-screen television. Natural light pours in through large windows, complemented by a skylight. A cozy fireplace is situated beside a textured black rug on the floor, adding warmth to the space.

Townhouse in Bartlett

Spacious Family Vaca Storyland*Saco*Close to all!

5 out of 5 average rating, 43 reviews

The exterior of a spacious, multi-level cottage is shown against a colorful sunset. Stone and wood detailing adds character, while large balconies enhance the charm. A well-manicured lawn features greenery and blossoming flowers, creating a welcoming approach.

Home in Bethlehem

White Mountains' Inn, Bretton Woods, Loon, Cannon!