Vacation rentals in Winn

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Top-rated vacation rentals in Winn

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Top guest favorite
A lakeside cottage is nestled among trees, featuring wooden siding with flower boxes beneath the windows. The property slopes down to a clear lake, with light filtering through the surrounding foliage, creating a serene natural environment.
Cottage in Lincoln
5 out of 5 average rating, 105 reviews

The Nest will be your Maine recreational retreat!!

The Nest is our lakeside cottage in the ❤️ of Maine’s recreational playground. You are steps from a crystal clear spring fed lake; we are also situated on ATV and snowmobile trails. Enjoy the calls of the loons & waves lapping at the shore; take in the incredible sunsets over the lake & unwind in front of the fire. We welcome your well behaved pups, please review our house rules for pet details. This is the perfect spot to recharge your batteries. We look forward to seeing you at The Nest!

Top guest favorite
A tiny home features a covered porch with wooden screens, surrounded by green grass and trees. A red firepit structure sits on a stone base nearby, enhancing the outdoor space. A gravel driveway leads up to the home, suggesting ample parking.
Tiny home in Howland
5 out of 5 average rating, 72 reviews

The Howland Hideout

Welcome to The Howland Hideout | Cozy Private Maine Retreat for Couples, Solos & Small Families. Filled with the necessary amenities for a comfortable stay and boasting handcrafted touches throughout, you won’t find many places quite like this! Could be a great fit for traveling nurses as there are multiple hospitals nearby. This family friendly location has a large parking area with plenty of room for vehicles/trailers and the patio/backyard are a great place to relax and enjoy the outdoors.

Top guest favorite
A functional kitchen area features wooden cabinetry and a white stove and refrigerator. A round wooden table with a single chair is positioned nearby, contributing to a cozy atmosphere. Small kitchen appliances are neatly arranged on the countertop, with a sink visible under the cabinets.
Apartment in Medway
4.96 out of 5 average rating, 91 reviews

Elkins Rental

A peaceful place for the family. If you're looking for a quiet out of the way place to stay but still close to all the recreation this area has to offer, this is the place. Baxter state park and Katahdin Woods and waters National Monument close by. ATV trails, Snowsled trails and the Penobscot river all within a couple of miles away . Excellent area for hunting, fishing, hiking, boating and all other 4 season outdoor activities. Plenty of parking area for snowmobile, atv and boats trailers.

Top guest favorite
A charming cabin features a wooden deck with seating, surrounded by lush greenery. Tall trees and a serene atmosphere are present. The exterior showcases log construction and several large windows, allowing natural light to enter the interior.
Cabin in Lincoln
4.95 out of 5 average rating, 38 reviews

Peaceful Cabin on Center Pond

Relax any time of year at our peaceful cabin in the Maine woods. Situated on the shore of Center pond, the cabin has been appointed with all the amenities you would hope to find. 2 bedrooms each with a Queen sized bed (1 up-1 down) a loft with 2 twin beds, and 1 & 1/2 baths, the cabin comfortably sleeps 6. Upstairs is accessed by a spiral staircase. The fully furnished kitchen has everything you need to cook a full meal. Relax and sunbathe, swim, paddleboard or kayak the Summer days away.

Top guest favorite
Home in Lincoln
5 out of 5 average rating, 14 reviews

Family Waterfront Home with Cedar Barrel Sauna

Experience the beauty of Maine at our waterfront home perfect for up to 8 guests. Enjoy stunning water views from the screened porch, kids’ treehouse, and expansive dock. Explore with the provided kayaks, paddleboard, and canoe, unwind in the new cedar barrel sauna, or relax by the fire pit and listen to the loons. Cook on the 36-in. Blackstone grill. Close to Mt. Katahdin and Acadia Nat. Park. Swim, fish, ice skate, snowmobile—there’s something for everyone in this unforgettable setting.

Guest favorite
The open-concept living area features two wooden-framed sofas with dark leather upholstery, positioned on a patterned rug. A spiral staircase leads to the loft above, surrounded by warm wooden walls and illuminated by pendant lighting.
Cabin in Weston
4.96 out of 5 average rating, 71 reviews

Beautiful Log Cabin near East Grand Lake, Maine

OPEN WATER FISHERMEN, the cabin is located CLOSE TO EAST GRAND LAKE (1/2 mile to the Butterfield Landing boat launch and large parking lot). High Speed Internet, Super Clean, No Clutter & Heats Easily. Located on Rt 1, Weston. The East Grand Lake area is a well known destination for fishing, boating, snowmobiling, deer & grouse hunting. The camp is 3.5 miles to Danforth center. SORRY NO ATVs on the property. NO PETS, 2-night min. with 3 night-min. during peak season, mid June-labor Day.

Top guest favorite
A fire pit surrounded by stone offers warmth and light against a darkening sky. A spacious, newly renovated farmhouse with large windows is visible in the background, accentuated by the soft glow of outdoor lighting. Chairs are arranged nearby for seating.
Home in Lincoln
4.9 out of 5 average rating, 30 reviews

Lincoln Park Lakeside

LARGE yard and centrally-located! Your family will be close to everything when you stay at this lake view home. Bring your boat/trailer or water toys for all recreational water sports, fishing and swimming! Boat ramp just steps from house, along with public beach and dock, playground, ping pong table, and basketball court. Walk downtown just a block away to Restaurants and stores. Stroll over to Steaks N Stuff to grab some premium meat to throw on the bbq or just hang out in the yard

Top guest favorite
The cabin is nestled on the edge of South Twin Lake, surrounded by lush trees. A deck extends over the calm water, providing scenic views. The structure features a modern design with a metal roof and large windows, reflecting a serene, natural atmosphere.
Cottage in Indian Purchase Township
4.94 out of 5 average rating, 36 reviews

Luxurious and very private lake front cottage

This lakefront cabin is about 10 miles from Millinocket Maine and near Baxter State Park. Take it easy at this unique and tranquil getaway. The deck of this amazing property sits out over the beautiful waters of South Twin Lake. Spectacular views await you from both the inside and outside of the camp. This very private property consists of the entire peninsula. There is a large dock that is great for fishing, boating and swimming on the opposite side of the peninsula.

Superhost
Cabin in Glenburn
4.79 out of 5 average rating, 127 reviews

Acadia Pines Cabin w/HotTub 10min2Downtown

Welcome to Acadia Pines Retreat, where the whispering pines and peaceful forest trails set the tone for your perfect Maine escape. Nestled just a short drive from Acadia National Park and the coast, this charming retreat offers the serenity of the woods with the comforts of home. * Peaceful, secluded location *Private hot spa jacuzzi to soak in after a day of hiking *Outdoor seating and stargazing spots 📍 Centrally located for day trips, lobster shacks, and scenic drives

Superhost
The charming cabin features a wooden exterior with a metal roof, framed by two inviting porches. The front porch is accessed by steps, while the surrounding area includes wildflowers and greenery, creating a peaceful outdoor setting. A gravel path leads to the cabin.
Cabin in Medway
4.89 out of 5 average rating, 70 reviews

Log cabin on river on snowmobile trail and beach.

Cozy 4 season cabin on East branch of the Penobscot river, across the road from Medway recreational beach, on ITS 83 snowmobile trail. 2 Cabins for rent on property. Snowmobiling, fishing, kayaking, swimming, outdoor sports. Katahdin Woods+Waters, Baxter state park,+Ripogenus gorge a short drive away. 1 double and 2 twin beds. Meander down a grassy path+ have lunch or a fire directly on river. Large circular driveway for snowmobile parking.

Guest favorite
A serene lakeside view features a grassy area leading to Cambolasse Pond. A stack of firewood stands neatly beside the water's edge, while a small boat is visible on the calm lake. Lush trees and a clear blue sky complete the peaceful setting.
Cottage in Lincoln
4.74 out of 5 average rating, 87 reviews

Home with Sandy Beach On Cambolasse Pond

Welcome to Lincoln! This Camp is Located on a beautiful 1.3 acre flat lot with ample parking, sandy beach, shallow lake access and the ability to launch your own boat right from shore! Excellent snowmobiling,swimming, boating and fishing. Located on Cambolasse Pond there is not many like this. Private pond, Very peaceful Comes with sheets, pillows, and some towels. I recommend bringing extra towels and any other essentials you may need.

Top guest favorite
Home in Island Falls
5 out of 5 average rating, 15 reviews

Grandma’s Cozy Cabin

Relax with the whole family at this cozy rustic cabin, that sits on 45 acres, surrounded by wildlife. If you’re looking to relax with nature this cabin is the place to stay. This cabin provides 2 private rooms each with queen beds, a loft that has a queen and a full beds. The ATV trail runs through the property and a short distance to ITS trails. Sit on the deck and relax and watch nature come to you.

Popular amenities for Winn vacation rentals