Holiday rentals in Madison

Sister A-Frame in Woods (A)

Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Please note some amenities are seasonal. Check out our other listing!

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.

Maine Cottage - HOT TUB, Dead End, 100+ft shore.

Great getaway any time of year. Need a winter getaway for a change of scene or pace? We have you covered. Go ice fishing, snowmobiling, sliding, ice skating & just 45 minutes to Sugarloaf. During the summer months come fishing, swimming, boating, golfing or attending Maine's oldest running summer theater, Lakewood, just yards away. When you rent for a week we provide 2 tickets to the show. Also, a high caliber restaurant is part of the attraction - eat dinner, enjoy the show, watch the sun set!

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!

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.

Upstairs apartment

Located right in town,you are within walking distance to several quaint little shops, restaurants, bars and pubs. This newly listed apartment offers 2 bedrooms with queen sized beds. The kitchen is nicely equipped. A great place to stay while experiencing many of the activities Maine has to offer. Minutes away from biking & hiking trail, snowshoeing and cross country skiing. Conveniently located near ITS trails, whitewater rafting, sky diving & a little over an hour to several ski areas.

Farmington! Walk to town! Holiday family visits!

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.

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.

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

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!

Trailside Cabin

Come & play in the beautiful mountains of western Maine! Cozy, rustic cabin for two. Enjoy miles of multi use trails right off the front steps! If you decide to venture away from the cabin, Rangeley's Saddleback Mt & Sugarloaf USA are both 35 miles away & the college town of Farmington is just 15 minutes south. Our cell service is terrific, but there's no tv or wifi...come to the woods & unplug!