Holiday houses in Madison

5 out of 5 average rating, 134 reviews

Cabin in Chesterville

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

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)

5 out of 5 average rating, 117 reviews

Cabin in New Portland

Cozy Cabin on the Carrabassett River

Enjoy four seasons of recreation while staying in a comfortable cabin overlooking the beautiful Carrabassett River. The cabin is nestled in 17 private acres but is close to services and restaurants, trails, and the iconic Wire Bridge. Snowmobile trails are accessible from the cabin, and ATV trails with parking are accessible from nearby Kingfield (6 miles north). Ski Sugarloaf, bike the Carrabassett Valley trails, hike the Bigelow Preserve, or just relax by the river - this area has it all!

4.93 out of 5 average rating, 166 reviews

Cabin in New Portland

Cozy cabin with Hot Tub on Lemon Stream

Relax at this unique, conveniently situated 2 bedroom cabin located on Route 27 between Farmington (15 miles) and Kingfield (7 miles). For winter skiing and summer activities as well, Sugarloaf is just 30 minutes away. The cabin is just off the main road to minimize weather issues. Lemon Stream runs through the property and you can go fishing and explore the 3 acre woodland. Nicely furnished with new appliances, a new hot tub, and all the amenities, this little cabin is the perfect getaway!

4.92 out of 5 average rating, 120 reviews

Home in Starks

Heavenly 4bd farmhouse in Maine.

Medicine Hill is a 125 acre farm on the Sandy river complete with an old fashioned swimming hole and an entire island to explore. We grow a wide variety of 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 taking it all in. 4 bedrooms have incredible views and are surrounded by trees or fields. And if the Chef is available..eat!

4.97 out of 5 average rating, 220 reviews

Home in Farmington

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.

4.96 out of 5 average rating, 363 reviews

Apartment in Kingfield

On The River 2 with Lucy the resident cat

On the River 2 is located in the heart of the historic downtown Kingfield on Main street with river views of the Carrabassett river. Miss Lucy Lu (Lucy) is the cat residents who lives in this special apartment. She is the host and will greet you. She loves people. She is an indoor kitty. There is a restaurant next door, the gallery is downstairs, swimming out the back of the building. Sugarloaf mountain close by. Mountains of possibilities to explore in the western area of Maine.

4.98 out of 5 average rating, 172 reviews

Cottage in Farmington

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.

4.82 out of 5 average rating, 430 reviews

Cabin in Skowhegan

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.

5 out of 5 average rating, 117 reviews

Guesthouse in Cornville

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"

4.99 out of 5 average rating, 325 reviews

Cabin in New Sharon

Kate-Ah-Den Cabin, a soul soothing escape.

Secluded & artistically built - a cozy cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

4.85 out of 5 average rating, 142 reviews

Home in New Portland

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!

4.89 out of 5 average rating, 100 reviews

Apartment in Pittsfield

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!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Madison holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Madison

5 out of 5 average rating, 11 reviews

Home in Canaan

Zeus's Landing| Lakefront | Close to Colby

BryanRating, 5 stars6 days ago

Great location and price for our group. Beds were comfortable and house was very clean. We will be staying here next year!

4.98 out of 5 average rating, 65 reviews

Apartment in Kingfield

Village 2-Bedroom with Riverview

HarwantRating, 5 stars2 months ago

Ben was a great host! The apartment is perfect for 3-5 people and the location is perfect. 20 minutes to sugarloaf and walking distance to restaurants and a general store.

4.93 out of 5 average rating, 29 reviews

Cabin in Embden

2 BR Cabin on Beautiful Embden Pond!

DanaRating, 5 stars9 months ago

We had a great week at this lovely cottage! All the amenities we needed to enjoy time right by the water. Loved the comfortable beds and living room furniture…plenty of space to sprawl out even for a relatively small cabin. And I got what I needed most: kayaking and loons. We had a great week!

4.96 out of 5 average rating, 81 reviews

Apartment in Wilton

A Home away from Home.

KarenRating, 5 stars5 days ago

Linda and Bruce were fabulous host. The walking path down to the trout pond was enjoyable. The views outside were spectacular and you also had a great view from inside. I would definitely stay there again and bring my husband the next time. Thank you Linda and Bruce

4.89 out of 5 average rating, 75 reviews

Home in Avon

Sandy River Valley Farm House

BrennahRating, 5 stars1 week ago

Beautiful place, would definitely return! the area was private and quiet which was what we were looking for. we enjoyed seeing the cattle and sitting outside by the fire pit. our dog had a great time as well. host communicated well and was flexible.

4.8 out of 5 average rating, 20 reviews

Cabin in Embden

Beautiful 3 bedroom camp on Embden Pond!

BeverlyRating, 5 stars2 weeks ago

We had a great stay at Kayla’s place while in town visiting family. Plenty of space in the house for the 5 adults and 2 pre-teens in our group. We would stay here again if available. Thank you.

4.8 out of 5 average rating, 15 reviews

Home in Skowhegan

Cozy, Comfortable, welcoming With private suite

KatherineRating, 5 stars4 months ago

Marks place made our trip to visit family very comfortable and convenient to visit in the middle of winter. Very cozy and inviting and Mark was very attentive to ensuring our check-in and stay was great. If your looking for a great stay in Skowhegan with plenty of space and accommodation look no further.