Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Top guest favourite
A cozy living area features a modern electric fireplace encased in rustic wood, complemented by a circular coffee table. Soft seating offers comfort, while a wall-mounted television is positioned above. An adjacent entry leads to a spacious eat-in kitchen, creating an inviting environment.
Flat in Kingfield
4.9 out of 5 average rating, 386 reviews

On The River

On the River, airbnb is located in the heart of downtown Kingfield right off the snowmobile trail. Sleeps 6 people. Has a spacious eat-in kitchen with a vie looking out to the Carrabassett River. Steps away from galleries, gift shops, restaurants, bank, Stanley Museum. 20-minute drive up to Sugarloaf mountain ski resort and the breathtaking views of 4000ft peaks of the western mountains of Maine. In summer, fly fishing and swimming right out the back . In winter, there are many snow sports.

Top guest favourite
Cabin in Chesterville
5 out of 5 average rating, 162 reviews

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Guest favourite
A serene lake view captures the calm water reflecting soft hues of sunset. A dock extends into the lake, inviting peaceful moments, while colorful flowers border the rocky shore, enhancing the natural beauty of the setting.
Flat in Madison
4.92 out of 5 average rating, 62 reviews

Pa’s hangar on the lake

Quaint loft in old theatre colony on Lake Wesserunsett. "Pa's Hangar" in memory of my dad who designed and helped build our little place. It is a studio apartment complete with handicapped shower , Cook top, microwave , roasted coffee beans (fresh from our own roaster) Verismo machine, french press AND espresso machine! 3 ways to enjoy your coffee by the lake! Our home has lake frontage and the apartment is only a one minute walk to the lake for fishing, kayaking, or just listen to the loons!

Top guest favourite
The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.
Home in Farmington
4.96 out of 5 average rating, 265 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Top guest favourite
A cozy living area features knotty-pine walls and a comfortable seating arrangement with a blue sofa. A small coffee table sits atop a textured area rug. A television is positioned on a media console, illuminated by a nearby lamp. Two windows with patterned curtains allow natural light to fill the space.
Home in Farmington
4.99 out of 5 average rating, 225 reviews

Farmington! Walk to town & trails! Family-Friendly

We take great pride in providing a stay that you will remember for years to come. Our moose house is well-stocked with all essential amenities and a few extra surprises! Quaint, convenient neighborhood walking distance to UMF and downtown Farmington. Franklin Memorial Hospital is a short drive. Sugarloaf and Rangeley areas are 45 minutes. WIFI and smart TVs. (No cable.) Washer/Dryer with detergent available. Great place to stay for exploring Maine or a visit with your family and friends.

Top guest favourite
A private cottage is surrounded by lush greenery, nestled among trees. The entrance features a wooden deck with two chairs and a small table, inviting relaxation. A well-maintained stone path leads to the cottage, enhancing the private and secluded ambiance.
Cottage in Farmington
4.98 out of 5 average rating, 199 reviews

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Guest favourite
Cabin in Skowhegan
4.82 out of 5 average rating, 439 reviews

The Cabin -Skowhegan

Main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler. Loft has 2 twin beds. The couch could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large air fry oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/Blue ray player, Gas BBQ (May to November 1st.), as well as a picnic table, out door fire pit. For guest who are traveling by plane, towels are provided, upon request.

Top guest favourite
A tranquil outdoor space features a wooden pergola with seating and a grill, situated beside a hot tub. The fenced backyard is surrounded by tall trees, and the charming house is accentuated by a beautiful sunset sky.
Cabin in Kingfield
4.99 out of 5 average rating, 116 reviews

Cozy Cabin with Modern Amenities. Pet Friendly!

Kick back and relax in this beautifully renovated home with amenities you didn't know you were missing. Despite its small stature, every square inch is utilized, boasting 4 beds and 1.5 bathrooms, including a huge shower with multiple shower heads and hurricane force water pressure. Located on a quiet street just minutes from the Kingfield village, steps from the snowmobile trail system, and 20 minutes from Sugarloaf. Designed with dogs in mind, complete with a fenced in backyard.

Guest favourite
A spacious living area is showcased, featuring wooden walls and flooring. A cozy couch and an armchair provide seating, while a wooden dining set is positioned nearby. The kitchen area includes essential appliances, with natural light illuminating the space through a door and windows.
Home in Mercer
4.9 out of 5 average rating, 129 reviews

Moore's place

🇺🇸🏳️‍🌈Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets). Close to hiking, Sugarloaf, ME IT Snowmobile trails is .03 miles away,located between Farmington, Skowhegan, and Augusta If your looking for someone to take you on a hike, and or short kayaking trip, pontoon ride around Lake Wassookeag. moose head lake on a Saturday or Sunday , (with a fee) just let us know

Guest favourite
The exterior of a log home is displayed, featuring a large green lawn and surrounded by trees. A covered porch with seating and a gas grill is visible. Sliding glass doors open to the rear of the house, providing access to the outdoor space.
Cabin in Canaan
4.93 out of 5 average rating, 163 reviews

Loon Lodge Canaan,ME

Escape to this charming 2,000+ sq. ft log home on Sibley Pond, just 30 mins from I-95. Perfect for up to 8 guests, it features an open living/dining area with vaulted ceilings and rustic décor. Enjoy a new dock, spacious front yard for lawn games, and scenic views. Nearby snowmobile and ATV trails offer year-round adventure. A peaceful retreat for families and friends to relax, explore, and make lasting memories.

Guest favourite
The inviting living area features a stone fireplace with a mirror above it, surrounded by plants and wooden beams overhead. A wooden staircase leads to the upper level, while a dining area with several chairs is visible in the background, enhancing the warm and cozy ambiance.
Home in New Portland
4.86 out of 5 average rating, 156 reviews

The Riverfront Retreat - 27 minutes to Sugarloaf!

This vibrant farmhouse is surrounded by 800 ft. of Lemon Stream. Walk to the historic wire bridge! It is about 27 minutes to Sugarloaf and 8 minutes to Kingfield; located directly off Rt. 27 in route to Carrabassett Valley. You can hit the slopes then come home to a cozy, gas fireplace. There's a firepit by the stream to enjoy the stars in warmth. The home is full of color and organic decor. FAST STARLINK WIFI!

Guest favourite
The kitchen features light-colored cabinetry and a large island with seating for four. A spiral staircase is visible, leading to the upper levels. Natural light is provided by windows above the sink and in the dining area, which includes a wooden table and chairs.
Flat in Pittsfield
4.89 out of 5 average rating, 112 reviews

Loft Retreat

Welcome to our enchanting loft retreat! Our thoughtfully designed apartment offers a serene escape with a touch of sophistication. Ascend the spiral staircase to discover a cozy bedroom complete with a work space and reading nook. Hidden up a trap door on the third level are two twin beds for the nimble. A full deck complete with a small fire pit is available in the warmer months. Your getaway awaits!

Popular amenities for Madison holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Somerset County
  5. Madison