Holiday rentals in Chesterville

Off-Grid Cabin with 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- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Family · Location · Quiet

Lakefront Home w/ 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

Family · Location · Quiet

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!!!

Value · Family · River

Lakefront Log Cabin privacy-hot tub-dog friendly

Peace, privacy, in large, secluded waterfront cabin! Heavily wooded 2 acres on shore of lovely Maine pond. Cabin has 2,000 sqft on 3 levels, open, comfortable living. Beds: king, queen, 2 full, 1 twin, futon, two full bathrooms, fully equipped kitchen and pantry! Fast WiFi. Foosball, many board/card games. Meals at large picnic table on deck viewing lawn, water. Enjoy 4 kayaks, canoe, paddleboat, swim to raft, fish from dock or relax in a lounger. Endless outdoor activities, day trips.

Value · Family · Kitchen

Forest Bathing Lake Tiny Home: Kayak Fish Fire Pit

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Family · Value · Access

Close to Farmington! Newly Renovated Reset Retreat

Relax in this newly renovated 4-bedroom home on a quiet dead-end street in Wilton. Comfortably sleeps 1–10 with 3 queen beds, 1 king bed, and sleeper sofa. Enjoy a peaceful sunroom with backyard wildlife views, fully equipped kitchen, strong Wi-Fi, and dedicated workspace. Just 5 minutes to Wilson Lake, the hospital, snowmobile/ATV trail in the backyard, skiing at Sugarloaf, Saddleback, or Sunday River under an hour and local dining - perfect for short or long stays, families, or remote work.

Family · Location · Kitchen

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.

Family · Location · TV

Private, Modern 4 Bedroom Lakefront Escape

Welcome to Blueberry Point on Wilson Lake – Your Private Lakeside Retreat! Located on the shores of Wilson Lake in Wilton, featuring 250 ft of private frontage, 4 bedrooms, 3.5 bathrooms, a home office, and a game-filled rec room. Enjoy kayaking, canoeing, fishing, swimming, bonfires, and seasonal blueberry foraging. The yard is perfect for lawn games, BBQs, and relaxing year-round. In winter, explore snow-covered trails, ski nearby slopes, or simply enjoy the peaceful beauty of the lake.

Family · Location · Sleep quality

Lakefront Retreat, Boat Rental & Dogs Welcome!

A Magical Retreat on pristine Flying Lake, Amazing Views, Private Dock, Pontoon Boat Rental option & Kayaks-Perfect for a multi family/ friends getaway! Located on 200+ ft of PRIVATE Lakefront property with a Hot Tub, Theatre Room, 2 Kitchens, and so much more! 2026: Sleeps 16-22+, assuming 2/bed, seasonal Tiny House Option, Outdoor all season Hot Tub, Theatre Room, Fire Pit, 26 Acres *AWD required in winter months. Lots of parking, fishing, snowmobiling & ITS Trails & Close to Skiing!

Family · Value · Access

Relaxing Maine Woods Cabin on a Pond-Dog Friendly!

Wake up to the pond. This spacious, secluded waterfront cabin sits on 8 private acres in the Maine woods. Inside, you'll find 1,700+ sq. ft. of open, comfortable living space with 3 queen beds, a Murphy bed workspace/guest room, 2 full bathrooms, a fully stocked kitchen, and fast Wi-Fi throughout. Plenty of room for a group to gather or spread out. Outside, launch one of the kayaks or the canoe, fish off the dock, watch the sun set over the water, or just sit and listen to the quiet.

Location · Family · Bathroom

Quiet Cabin Retreat • Hot Tub • Trails

A quiet, cozy cabin surrounded by forest and complete privacy, tucked away on a dead-end road with no traffic or noise — just nature, calm, and comfort. Set on nearly 6 private acres, the property features a private walking trail through the woods, perfect for morning walks, relaxing afternoons, or simply reconnecting with nature. Ideal for couples, solo travelers, or small families looking for a peaceful getaway to slow down, unwind, and enjoy the beauty of Maine in every season.

Location · Family · Outdoor spaces

Lakeside retreat on quiet cove on Cobbessee Lake!

Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

Value · Family · Access