Holiday rentals in Madison

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!

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

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!!!

Springside Farms Memory Lane upstairs apartment

Step Back in time at this 1800 's Colonial New England Farm home upstairs Apartment. Watch dairy cattle grazing in the pasture near by. Only 35 minutes from Sugarloaf ski resort. Snowmobile ITS 84 trail is just feet away. Plenty of parking for trailers . Experience the spectacular fall foliage this area has to offer. Our farm has a large roadside stand for over 35 years. Take pictures with the pumpkins on this traditional New England farm stead. Your own private entrance leads to the upstairs.

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.

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.

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.

2 BR Cabin on Beautiful Embden Pond!

Relax with the entire family at this peaceful cabin, just a short walk from the public boat launch and centrally located to access the region's numerous outdoor recreational activities. Choose a season: boating, canoeing, whitewater rafting, or golfing in summer; hunting or enjoying fall foliage in autumn; skiing, ice fishing, or snowmobiling in winter. There are also extensive ATV/UTV trail systems, or simply relax and enjoy the sounds of nature from one of the best lake views!

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Bear Cub Lodge

Nestled in Starks, Maine, this rustic-modern log cabin offers a serene retreat. Primarily crafted from trees on the property, This brand new build boasts a handcrafted log exterior and modern interior comforts. Large windows, a crackling fireplace, and a spacious kitchen invite relaxation. Outside, a sprawling covered deck offers stunning views. Whether for a peaceful escape or outdoor adventures, this cabin strikes the perfect balance of rustic allure and modern convenience.

Cozy cabin in Solon, free WiFi

Get ready to relax in this 3-bedroom cabin in Solon. The cozy interior features 3 queen beds and 2 twin beds, perfect for a group getaway. With free fiber WiFi available, you can stay connected while enjoying the peaceful surroundings. The bathroom offers a refreshing shower to start your day. We hope you enjoy what our place and Solon has to offer. (Please note the price is for 2 people. each additional guest you can add in the reservation for 40$ per person per night)

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!