Holiday rentals in Winn

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Top-rated holiday rentals in Winn

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Top guest favourite
A hand holds a cup labeled 'Maine' against a backdrop of shimmering water reflecting vibrant autumn foliage. The still water is bordered by large rocks and trees, enhancing the serene atmosphere.
Cabin in Burlington
4.95 out of 5 average rating, 202 reviews

Secluded Waterfront Cabin

Please Message me to ask about possible discounts and length of stay minimums. Secluded four season cabin is located on remote Saponac Lake in Burlington, Maine. Last camp on a private dead end road with clear views of the lake. Perfect location for fishing, kayaking, or just relaxing in a hammock. Fully furnished with A Minisplit Heat Pump/ AC, and Propane "wood stove" well water, and high speed WiFi. Within 30 minutes of Lincoln and 1 hr of Bangor. Both towns have shopping, restaurants,etc.

Top guest favourite
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, 94 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 favourite
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, 57 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 favourite
A cozy camp is surrounded by tall trees, showcasing a classic A-frame roof and a porch with seating. The white exterior is complemented by green trim, while areas of orange pine needles cover the ground. The setting reflects a serene, natural atmosphere.
Cottage in Brownville
4.98 out of 5 average rating, 118 reviews

Perfect Lakeside Getaway!

The perfect lakeside getaway spot with beautiful views. It is renovated with an old time cozy camp feel, with modern conveniences. This pet friendly camp is across the street from Schoodic Lake. The cozy camp sleeps 5-6 comfortably with on-site parking for three. The camp is located on ITS 111 trails for snowmobiling and ATVing. Hunting, fishing and hiking destinations include, Baxter State Park, Gulf Hagas, and Katadin Iron Works. Water access at Knights Landing just a short distance away.

Guest favourite
The A-frame chalet features a green metal roof and a wooden exterior, set amidst lush greenery. A small balcony with flower pots is visible on the upper level, while a vintage vehicle is parked nearby on the grass.
Tiny home in Atkinson
4.95 out of 5 average rating, 157 reviews

Cozy Rural A-Frame in the Middle of Maine.

Get away from it all when you stay under the stars. This chalet is right on the ITS trail, nestled in the middle of a small lightly wooded lot in a rural setting. Enjoy the fire pit, bring your snowmobiles, bikes and trailers. The space is cozy with a 55" TV and small kitchen to prepare your meals. The bedroom is in the loft with catwalk opening up to a balcony. Enjoy access to year round outdoor activities as you are nearby Katahdin Iron Works/Jo Mary region and near Sebec and Schoodic lakes

Guest favourite
The interior of the custom-built yurt features a high, circular ceiling with a skylight at its center. A modern kitchen with stainless steel appliances is visible, alongside a spacious countertop. A loft area is accessed by a wooden staircase, with wooden beams and walls enhancing the natural aesthetic.
Yurt in Medway
4.95 out of 5 average rating, 163 reviews

Katahdin Riverfront Yurt

Glamping at its best! Beautiful custom built yurt on the banks of the Penobscot river along the Grindstone Scenic Byway. Close to Baxter State Park and majestic Mount Katahdin as well as Katahdin Woods and Waters National Park. Two miles to Penobscot River Trails with miles of groomed cross country skiing and mountain biking. 4 seasons of hiking, biking, fishing, canoeing, kayaking, white water rafting, skiing, and miles and miles of snowmobiling! 1 hour to Bangor 2 hours to Bar Harbor

Guest favourite
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.
Flat in Medway
4.95 out of 5 average rating, 82 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 favourite
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
4.93 out of 5 average rating, 29 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.

Guest favourite
The exterior of a modern white lodge is displayed, featuring a combination of large windows and a sloped roof. Lush green lawns and carefully arranged landscaping surround the entrance, showcasing contemporary architectural design.
Home in Lee
5 out of 5 average rating, 10 reviews

Silver Lake Lodge

Welcome to Silver Lake Lodge! Sun yourself on the dock and cool down in the crystal clear water. When the sun goes down, you can build a campfire, isten to the loons calling and maybe even catch some northern lights. Silver Lake is an ideal spot to revel in summer! If the weather doesn’t cooperate, no worries! You’ll have endless ATV trails to explore or hang out in the beautiful home playing games or streaming a movie. If you like to cook, you will be inspired by the gourmet kitchen.

Guest favourite
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
4.88 out of 5 average rating, 25 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

Superhost
Cabin in Glenburn
4.77 out of 5 average rating, 108 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

Top guest favourite
A serene lakeside scene features a wooden dock extending over calm waters, framed by tall trees. A stone fire pit is situated on the shore, and neatly stacked firewood is visible nearby. The sky transitions to soft pastel colors at sunset, reflecting on the lake.
Cottage in Millinocket
4.92 out of 5 average rating, 170 reviews

Lozier’s Lakefront, Fish, Swim, Campfire, repeat

Lozier’s Lookout is a cozy two-bedroom, lakefront cottage on beautiful Millinocket Lake. Perfect for both adventure and relaxation, guests can enjoy nearby hiking, biking, ATV'ing, and local dining, or stay close to home casting a line off the dock, swimming in the lake, paddling the provided kayaks or canoe, and gathering around the campfire for s’mores. With the charm of a classic cabin and the comforts of home, The Lookout offers a welcoming retreat in every season.

Popular amenities for Winn holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Penobscot County
  5. Winn