Vacation rentals in Madison

4.93 out of 5 average rating, 285 reviews

A charming tiny house is nestled amongst greenery, featuring a sloped roof and white exterior. A wooden fence provides privacy while a welcoming front porch offers seating. Natural stone pathways lead to the entrance, inviting guests into a serene outdoor setting.

Tiny home in Tamworth

Tiny House - *5 star Cleanliness - Outdoor Shower!

Tiny House living at it's best! Private outdoor yard space for grilling & chilling! A full bathroom inside & an outdoor shower with hot water! The perfect place to relax after a hike! A place for a comfortable and relaxing getaway, with lakes, rivers & mountains at your doorstep! Only 1 hour to the Atlantic coast! Just 2 hours north of Boston. Under 4 hours to the Canadian Border just 30 minutes to North Conway. The famous Tamworth Farmer's Market is within walking distance (Saturday mornings).

4.94 out of 5 average rating, 170 reviews

An inviting screened-in porch features two white lounge chairs adorned with dark blue cushions, positioned around a wooden coffee table. Natural light filters through large windows, revealing a wooded landscape outside. A ceiling fan rotates gently above, adding to the tranquil atmosphere.

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.

4.98 out of 5 average rating, 531 reviews

The exterior of a wooden over-garage studio is shown, featuring a steeply pitched roof and large windows that allow for natural light. A long, paved driveway leads to the entrance, framed by greenery and stone landscaping on either side.

Guest suite in Conway

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.

4.89 out of 5 average rating, 152 reviews

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

4.9 out of 5 average rating, 514 reviews

Cabin in Tamworth

Luxurious Mountainside Cabin! Fantastic Views!

Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Giant Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets ok! *Pet Fee Applies! *Additional Fee for Sauna

4.82 out of 5 average rating, 451 reviews

A compact corner sink is mounted on the wall, featuring a chrome faucet and two dispensers of soap. The wall displays a light cream color, and the floor is covered with gray tiles. An electrical outlet is visible nearby.

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!

4.94 out of 5 average rating, 237 reviews

A private dock extends over calm waters, featuring two white Adirondack chairs positioned for tranquil lake views. Lush trees line the shoreline, and the sky is filled with scattered clouds, enhancing the serene atmosphere.

Tiny home in Bethlehem

The Uncommon Loon: A Lakeside Tiny Home Experience

Welcome to the Uncommon Loon in Whitefield, NH! Your uncommonly calm retreat away from all the stress of the real world. This freshly renovated, stunningly simple tiny house is nestled on beautiful Forest Lake, New Hampshire. Brew yourself a fresh cup of coffee, take in the mesmerizing sunrise views, and listen to the call of the Loon from your own personal dock. Whatever your goals are when visiting this tiny paradise, you’ll leave relaxed, revitalized, and ready to come back again.

5 out of 5 average rating, 112 reviews

The exterior of a newly built guesthouse is displayed against a clear sky, showcasing modern architecture with a dark grey facade and a sloped metal roof. Snow covers the ground, while trees border the property, suggesting a peaceful rural setting.

Guesthouse in Hiram

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!

A cozy fire pit area features eight blue adirondack chairs arranged in a circle around a stone fire pit. Soft lighting from hanging bulbs illuminates the surrounding trees, creating a welcoming outdoor space for gatherings.

4.97 out of 5 average rating, 147 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, 347 reviews

A charming cottage is situated by the water's edge, framed by tall trees. The exterior features a metal roof and flower boxes. A stone pathway leads from the cottage to the shoreline, where a kayak is visible in the background, adding to the serene lakeside atmosphere.

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!

5 out of 5 average rating, 97 reviews

Cabin in Madison

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.

4.96 out of 5 average rating, 226 reviews

A serene riverside view is presented, featuring a red kayak by a wooden dock. Lush green trees frame the scene, with vibrant autumn foliage visible in the background. The calm waters of the Ossipee River reflect the natural surroundings, creating a peaceful atmosphere.

Cabin in Parsonsfield

Riverfront cabin between Portland & White Mtns.

Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Madison vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Madison

A spacious living room features high vaulted ceilings with wooden beams and large windows that allow natural light to fill the space. A stone fireplace serves as a focal point, while a comfortable sectional sofa and sleek coffee table add to the inviting layout.

5 out of 5 average rating, 7 reviews

Wolf Lodge with outdoor Jacuzzi Luxury, Brand New

The bathroom is equipped with a marble countertop sink and a large mirror. To the side, a stackable washer and dryer are positioned. Natural light enters through a window adorned with blinds, complemented by a minimalistic black and white wall art piece.

4.86 out of 5 average rating, 7 reviews

Redwood Retreat | Lake Access | Mtn. Getaway

5 out of 5 average rating, 19 reviews

An open living area is presented with a comfortable sofa and additional seating around a wooden island. A black refrigerator and modern kitchen fixtures are visible. Natural light fills the space through large windows, and a wood stove is positioned nearby for warmth.

Home in Fryeburg

Fryeburg home away from home

5 out of 5 average rating, 16 reviews

A serene lakeside scene features a sandy beach curving along the water's edge, with gentle waves lapping at the shore. A wooden dock extends into the lake, surrounded by lush green trees under a partly cloudy sky. Benches are positioned on the beach for seating.

Home in Tamworth

King Bed| Ensuite Bathroom|Playground|Game Area

4.92 out of 5 average rating, 12 reviews

An aerial view of a spacious cottage surrounded by lush greenery and trees. A winding brook flows nearby, with the cottage featuring a mix of gabled roofs and large windows. Outdoor seating areas are visible on the deck, inviting relaxation in the natural setting.

Guesthouse in Madison

Quiet Brookside Midweek Escape – Book Now & Save

An outdoor seating area features two Adirondack chairs positioned around a circular fire pit. The ground is covered with a light layer of snow, and surrounding trees provide a natural backdrop. A wood pile is visible nearby, enhancing the rustic atmosphere.

4.87 out of 5 average rating, 52 reviews

Mountain View | Ski Town | Fireplace |Hiking Trail

A tranquil scene at dusk showcases a still body of water reflecting a bright full moon. The surrounding landscape features dark silhouettes of trees and distant hills under a deep blue sky. Gentle ripples disrupt the mirror-like surface of the water.

4.9 out of 5 average rating, 110 reviews

Distinctive charm on 2 wooded acres

The living area features large windows that provide ample natural light and views of the surrounding trees. A coffee table sits in the center of the room, accompanied by a comfortable seating arrangement. A flat-screen television is mounted on the wall opposite the windows.