Ski-in/Ski-out holiday rentals in Owls Head

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Top-rated ski-in/out rentals in Owls Head

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Guest favourite

Guest suite in Hermon

4.86 out of 5 average rating, 203 reviews

Lake House Cottage

Cozy Two-Bedroom Apartment on Hermon Pond, Hermon, Maine Enjoy a charming two-bedroom apartment attached to our home, just 5 minutes from the interstate, 20 minutes from Bangor International Airport, and about an hour from Acadia National Park. With our long private driveway and the serene pond in the backyard, you’ll feel like you’re in the middle of nowhere. Recently remodeled, the apartment exudes a cozy camp vibe with wide yellow pine walls, hidden doors, and beautiful views of the lake.

Top guest favourite

Yurt in Appleton

4.97 out of 5 average rating, 286 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Cabin in Embden

4.89 out of 5 average rating, 44 reviews

Embden Earthship - Lakefront Getaway by Sugarloaf

Escape to a handcrafted, eco-friendly lakeside retreat. Set on 8.27 private acres, this unique cabin offers direct access to a 194-acre lake, 470 feet of waterfront, and trails through lush woods. Enjoy snowmobiling, ice-fishing, snowshoeing, and cross-country skiing right outside your door. Relax by the lake, explore the orchard, or soak in panoramic forest views from every room. Just 50 minutes to Sugarloaf for downhill skiing, this peaceful haven blends rustic charm with sustainable living.

Home in Westport

4.82 out of 5 average rating, 11 reviews

Captain's Quarters

Enjoy beautiful views of the wide Sheepscot River from the updated 1842 Captain Pinkham House and salt water farm where the island's boat building industry began. Twenty acres of shore frontage, fields, and woodlands await your discovery. Or launch your kayak from the dock and explore the many local rivers and coves. And of course just relax in the cool sea breezes, or on the screen porch, or even curled up inside by the fire. Treat yourself. More updates and improvements for the 2025 season.

Superhost

Flat in Hallowell

4.71 out of 5 average rating, 147 reviews

2 bed down apt with no cleaning fee or checklist

This is a charming 1st floor apt with 1.5 baths/bidet, granite countertops and wood floors, fully stocked galley kitchen, dining area, desk space. living room with working fireplace/wood stove for winter use, large deck overlooking the Kennebec River/park. Year round hot tub, sauna and gym are located in the building next door. Just 2 blocks from bustling downtown Hallowell. Can be reserved as a 1 or 2 bedroom. The small bed is an LL Bean cot. Bicycles and kayaks available in season.

Top guest favourite

Cottage in Blue Hill

4.97 out of 5 average rating, 114 reviews

Chic Farmhouse Cottage, WiFi, Private Beach, A/C

Scrupulously appointed with authentic mid-century classics mixed with farmhouse accents. Total privacy guaranteed, NO hidden cameras, 600 sqft cottage with private, furnished, covered deck and a private fenced-in & furnished garden with a natural stone fire-pit, & ROW to private beach. High speed internet, 500Mbps, cold A/C, small kitchen equipped for basic, minimal cooking. Relax on the Adirondack chairs, grill by the fire pit or dine al fresco in the garden. Parking for 2 cars.

Superhost

Cabin in Brooks

New place to stay

Cozy Lakefront Cabin * CampChamp

Retreat. Rest. Rejuvenate. Welcome to Camp Champ Tucked away in the heart of Maine’s natural beauty, Camp Champ is a lovingly curated cabin perched right on the edge of a pristine lake. Whether you're craving summer swims and canoe adventures or winter wonderland vibes with snowshoes and hot drinks by the fire, Camp Champ is the kind of place where you lose track of time—in the best way. A place to disconnect from the busy and reconnect with nature, each other, and yourself.

Guest favourite

Cabin in Newport

4.9 out of 5 average rating, 21 reviews

Lake View Hide Away

Nestle away in the woods with water views of the lake and direct access to the atv trail . No trailering , drive the atv right from the drive way to the trails. So much to do here. After spending the day walking , fishing, enjoying an outside fire or just exploring the maine woods,soak in the hot tub, take in the peace and quiet, or an infrared sauna session. Relax and unwind in-front of our beautiful fire place.. Trail links up to the International trail system(ITS)

Top guest favourite

Guest house in Cornville

5 out of 5 average rating, 114 reviews

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"

Top guest favourite

Home in Oakland

4.89 out of 5 average rating, 95 reviews

Lake-House on water, East Lake, Near Waterville

Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

Superhost

Home in Owls Head

4.65 out of 5 average rating, 17 reviews

Beautiful Harborview Farmhouse

Beautiful serene setting and warm comfortable stylish home just minutes from beaches, cool towns, nationally acclaimed restaurants and Farnsworth Art Museum. We have received all 5 star reviews since our children flew the nest!! (and I could keep up with things:). The reviews include saying what a bargain our price is for the comfort and expansive property you will have. It is our FT home and we just rent occasionally when we are upta camp or away.