
Vacation rentals in Madison
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Madison
Guests agree: these stays are highly rated for location, cleanliness, and more.

Off-Grid Escape. Wood Fired Hot Tub. 4 Kayaks
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)

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!!!

Pristine, Peaceful Kingfield Chalet
Just a short 15-20 minute drive from Sugarloaf and 3 minutes from historic downtown Kingfield, this chalet provides a peaceful, private respite after a busy day on the mountain. Our 2BR, 1BA eco-friendly chalet is tucked back from the road, with distant neighbors and fast WiFi. You can be surrounded by nature but only minutes from lovely restaurants, local shops, grocery store, gas station and tons of trails, rivers & lakes for snowshoeing, XC, snowmobiling, hiking, huts, MTB, kayaking & more.

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.

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

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.

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.

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.

Mill Pond Waterfront Cabin On The Way To Sugarloaf
***Please Message me to ask about possible discounts and length of stay minimums.*** Year round waterfront Cabin Located on a private road off Rte. 27 & on the way to Sugarloaf. Only 15 minutes to Farmington, about 30 to Carrabassett Valley & Sugarloaf area and about an hr. to the Rangeley and Saddleback Mtn. area. The cabin is situated on 2+ acres with tall trees and plenty of wildlife. Come relax on the covered porch overlooking the pond or around the fire pit

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"

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.

Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.
Popular amenities for Madison vacation rentals
Stay near Madison's top sights
Lake side house rentals in Madison

Lake-House on water, East Lake, Near Waterville

Beautiful home on Wyman Lake

Salmon Lake Retreat

Lakefront: Private Hot Tub, Sauna & Free Massages!

Waterside Getaway

Modern Lakefront Home w/ Hot Tub • Winter Escape

Private Lake House, Firepit & Amazing Sunset Views

Lakefront 3 bedroom pet friendly on Messalonski
Other great vacation rentals in Madison

Modern Tiny Cabin Near Belgrade Lakes

Cozy Riverside Cottage

Private tiny cabin on six acres of trees

The Cottage at Red Top - Cozy Lakeside Year-Round

Charming 2 bedroom cabin on Clearwater lake

Terrapin Station @ Porter Lake – Lakefront Living

Cabin In The Birches #2

The Great Escape!
Destinations to explore
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Québec City Vacation rentals
- The Hamptons Vacation rentals
- Island of Montreal Vacation rentals
- Capital District, New York Vacation rentals
- Laurentides Vacation rentals
- Quebec City Area Vacation rentals
- Laval Vacation rentals
- Mont-Tremblant Vacation rentals
- Québec Vacation rentals
- Portland Vacation rentals





