Vacation rentals in Winn

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Top-rated vacation rentals in Winn

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Guest favorite

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, 194 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 favorite

An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.

Home in Hampden

5 out of 5 average rating, 113 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

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, 90 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, 36 reviews

The Howland Hideout

Welcome to The Howland Hideout! This unique tiny home is the perfect getaway spot for all seasons, 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.

Superhost

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, 149 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 favorite

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

4.96 out of 5 average rating, 140 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

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

4.95 out of 5 average rating, 75 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

4.96 out of 5 average rating, 24 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 favorite

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, 5 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.

Top guest favorite

A cozy living area showcases a brown leather sofa paired with a decorative side table. A patterned area rug is centered between the seating and a fireplace. Across the room, a dining table accommodates six and is bathed in natural light from large glass doors leading to the outdoors.

Home in Enfield

5 out of 5 average rating, 19 reviews

NEW Water’s Edge Lake House on Cold Stream!

Located right on the shoreline, our newly renovated lake house is the perfect place to stay no matter the season! Awash with natural light, the home has been thoughtfully renovated and designed for a comfortable, relaxing and convenient stay! Great swimming right off the dock, a short walk or bike ride to area beaches. We have kayaks and canoes available for use as well! CSP is one of the largest lakes in the area with great fishing, boating, ATV and snowmobile trails

Superhost

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, 70 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

A charming red cottage is situated by the lake, framed by autumn leaves. The building features a welcoming entrance with a small porch and a window, surrounded by a lush green lawn and colorful foliage, creating a peaceful lakeside setting.

Cottage in Sebec

5 out of 5 average rating, 138 reviews

Cozy All-Season Cottage on Sebec Lake in Maine

My little red Lake Cottage is located on pristine Sebec Lake in Piscataquis County in the middle of Maine. Small and cozy with combined kitchen + dining room , 2 bedrooms, sitting room, bathroom and deck overlooking the lake. Enjoy the beautiful sunsets and lake wildlife - and it is only about 15 minutes from Dover-Foxcroft with various shops and quaint eateries. I am only 30 minutes away and will be available if you have any questions!