Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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Top guest favorite
Home in Madison
5.0 out of 5 average rating, 15 reviews

The Shore House

Welcome to your perfect lakeside retreat on the peaceful shores of beautiful Lake Wesserunsett w/ 3 beds/1.5 baths! Main living area has natural wood, cottage ambiance & stunning wall of windows w/ gorgeous lake views. Enjoy private dock, canoe, kayak, 2 decks & large lawn for cornhole. Sleeps 6 w/ king, queen & full beds. Pet-friendly, Wi-Fi, 2 TV's & parking for 4. Mins to breweries, golf, snow trails, theater, skiing, dining & more. Perfect for year-round fun—swim, fish, boat, snowmobile!

Top guest favorite
A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.
Home in Starks
4.94 out of 5 average rating, 171 reviews

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

Top guest favorite
A bright sitting area features large windows offering scenic views of Porter Lake and surrounding mountains. Wooden walls create a cozy atmosphere. A comfortable couch sits adjacent to a flat-screen TV. Nearby, a bookshelf displays a variety of books, enhancing the inviting space.
Cabin in Strong
4.92 out of 5 average rating, 174 reviews

Lakefront Home with Dock | Porter Lake | Sugarloaf

Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views

Top guest favorite
Cabin in Industry
5.0 out of 5 average rating, 11 reviews

Misty Mtn. Lodge

Take a relaxing journey to this unique and subtly Lord of the Rings inspired cabin nestled in the woods and farms of Maine. Enjoy downtown Farmington and Clearwater Lake. Ski Sugarloaf or Titcomb Mountain. Explore new trails. Greet the resident cat, Mr.Boro who abides in the cellar. Stargaze around the firepit with smores and jam on the guitars offered here at your pleasure. You'll have full access to the Lodge including 2 bedrooms, full kitchen and bathroom with an open living room concept.

Top guest favorite
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
4.97 out of 5 average rating, 324 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 favorite
Home in Hartland
4.94 out of 5 average rating, 49 reviews

Waterside Getaway

Come getaway at our waterfront house located in Hartland Maine. This is a perfect spot to unwind and enjoy the peaceful water while relaxing and having fun with your friends and family . A 30 min drive to downtown Waterville where you can find shopping and dining places for the whole family . Enjoy fishing , swimming and more right outside your door . The house also has a boat launch and dock for your boat if you choose to bring one. We hope you enjoy staying at our home.

Top guest favorite
A wooden dock extends into a calm, misty lake, with a small boat moored alongside. The water reflects soft pink and purple hues from the sky, while silhouettes of distant hills provide a serene backdrop.
Guesthouse in Cornville
5.0 out of 5 average rating, 138 reviews

Quiet Retreat; Barker Pond Farm Cabins, LLC: Pine

Barker Pond Farm Cabins, built in 2010, feature modern amenities including a full bath and kitchen, outfitted with towels, linens and cookware. Each cabin sleeps 4 people, with a queen sized bedroom and a 2 twin sleeping loft, accessed by a ship's ladder. A screened-in porch is the perfect place to sit and listen to our resident loons. We offer two identical cabins for rent, Pine, listed here, and Spruce, which can be found under "Barker Pond Farm Cabins; Spruce"

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 453 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Guest favorite
A custom-built deck under a wooden pavilion overlooks the water. Two comfortable chairs and a side table are positioned on the deck, with a red umbrella providing shade. The tranquil lake is visible in the background, surrounded by trees and a small boat dock.
Cottage in Madison
4.86 out of 5 average rating, 57 reviews

Charlie's Perch -Charming Lakewood Cottage

Nestled in the historic Lakewood Community sits our waterfront home. Walk out of your bedroom door onto a custom deck overlooking Lake Wesserunsett. Enjoy sunsets and tranquil sunrises under the pavilion. Plan your day around fishing, swimming, boating and all the adventures Maine has to offer. Use of the lake is at your own risk and liability. By booking you and all of your quests hold harmless the host and resident of the lake. There is no life guard on duty.

Top guest favorite
Home in New Portland
5.0 out of 5 average rating, 22 reviews

Riverway Cottage

Welcome to Riverway! A cozy 2-bedroom cottage nestled beside the Carrabassett River. Just 30 min from Sugarloaf’s world-class skiing and snowboarding. Enjoy fly fishing, tubing, and swimming in the river or in the pool. Explore hiking, snowshoeing, snowmobile/ATV trails (no direct access from cottage). A short drive to Kingfield (15 minutes) and Farmington(1/2hr) shops & dining. We proudly offer 1-night stays-perfect for quick trips or last-minute overnights!

Guest favorite
A well-lit kitchen features wooden walls and a marble countertop. Essential appliances, including a refrigerator and a coffee maker, are visible. Natural light enters through two windows, reflecting off the cabinetry. A doorway leads to a warmly lit adjacent room.
Cabin in Starks
4.9 out of 5 average rating, 108 reviews

Private tiny cabin on six acres of trees

The tiny cabin is perfect for any individual or couple looking for a quiet private getaway. This newly renovated space is perfect for reading, sunbathing, napping, outdoor cooking, or walking your dog in the wooded area outback. The central location of the cabin is the jumping off point to other activities such as hiking, kayaking, whitewater rafting, bicycling, or exploring Farmington, a hip little college town nearby.

Top guest favorite
The cabin's exterior is framed by lush green foliage, showcasing a welcoming wooden porch with steps leading up to the entrance. The log cabin features large windows and a combination of wood and lattice detailing on the lower level, surrounded by a serene natural setting.
Cabin in Madison
4.94 out of 5 average rating, 31 reviews

Grace Landing

In the heart of central Maine our charming, secluded cabin is nestled on a peaceful dirt road. This spacious home offers 4 cozy bedrooms and 2.5 bathrooms, making it perfect for families or groups of friends. Whether you’re looking to relax by the fireplace, enjoy the serenity of the surrounding woods, or explore the nearby lakes and trails, our cabin has everything you need for a memorable stay.

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