Vacation rentals in Winn

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Top-rated vacation rentals in Winn

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Top 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, 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 favorite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.95 out of 5 average rating, 224 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Top guest favorite
A large cottage with a blue metal roof is framed by trees and large boulders. A spacious deck is visible at the front, which is bordered by black railings. Natural stone steps lead to the entrance, complemented by a gravel pathway.
Cabin in Wels
4.97 out of 5 average rating, 39 reviews

Family Friendly Lakefront Cottage, Ambajejus Lake

Bring the whole family to this great place with lots of room for fun. This is a large (1600 sq. ft.) kid friendly cottage that has all of the conveniences of a home with the beauty and charm of a lakefront cabin. The construction was finished in 2024 so everything is new including the furniture and appliances. The cabin waterfront is in a shallow cove. The depth at the end of the dock is less than 3 feet making it a good place for wading and exploring for kids. Water shoes recommended.

Top guest favorite
A wooden dock extends out over tranquil waters, flanked by lush greenery. The water's surface reflects the calm sky, creating a serene atmosphere. Steps lead down from the dock to the gently lapping water, inviting relaxation and aquatic activities.
Cottage in Glenburn
4.95 out of 5 average rating, 248 reviews

Your own private getaway on Pushaw Lake!

Welcome to Pushaw Lake! You’ll find all the comforts of home here! :-) Come for the weekend! Save 20% for a week, or 30% for a month stay! :-) Jump in the lake or go on an adventure in a kayak or canoe this summer! Bring snowmobiles, snowshoes, skis, or go ice-fishing this winter! :-) Relax... Read a book and listen to the Loons, or sit around the fire pit and say goodbye to stress! :-) You’re less than 20 minutes from Bangor International Airport, Downtown Bangor, and UMO! :-)

Top guest favorite
A spacious living area is highlighted by high wooden ceilings and large windows that allow ample natural light. Comfortable seating is arranged around a central ottoman, complemented by a large area rug. Artwork adorns the walls, adding to the inviting ambiance.
Home in Lowell
5 out of 5 average rating, 32 reviews

Lake House Oasis on Cold Stream

Enjoy a weekend away or an extended stay at our lakehouse oasis! High speed internet, cell phone booster and a full house automatic generator make this a perfect place to get away, while being fully connected. Perfect for vaca, remote work or a weekend away with plenty of space for the whole family! 4+ bedrms, 2 bath, chefs kitchen, lrg living rm and dining area, ample outdoor/lakeside seating, bonus loft spaces, game room w pool table and foosball, gym, sauna, sand volleyball, kayaks, & more!

Top guest favorite
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, 116 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 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
4.95 out of 5 average rating, 162 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 spacious living area features a large area rug with intricate patterns. A wall-mounted television is positioned above a simple white shelf adorned with books and plants. The open concept leads to a kitchen with white cabinetry and a doorway providing access to a bedroom.
Home in Orono
4.93 out of 5 average rating, 29 reviews

The River’s Nest

A Brand New Renovated Home!! Enjoy a stylish, relaxing stay at The River’s Nest, a cozy retreat in Orono, Maine. Nestled along the Penobscot River and just minutes from UMaine, this peaceful escape blends comfort, sophistication, and nature. Wake up to birdsong, sip coffee on the porch, and unwind in a thoughtfully designed space. Whether you're visiting campus, seeking adventure, or craving a quiet getaway, The River’s Nest offers the perfect mix of charm, culture, and outdoor exploration.

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
4.93 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.

Top guest favorite
A stylish bedroom features a spacious bed with intricate bedding, complemented by a decorative tapestry and an oil painting on the wall. Soft lighting from bedside lamps adds warmth, while a ceiling fan provides airflow in the inviting atmosphere.
Apartment in Old Town
4.95 out of 5 average rating, 118 reviews

The Sovereign Suite - Cozy/Convenient/Home Theater

Relax in this rural yet convenient apartment with easy access to Old Town and just a couple miles from I-95. Find comfort in a stylish bedroom or enjoy a premium home theater experience with a 77inch 4k HDR TV and surround sound. Well stocked kitchen and complimentary coffee and tea is included. New steam washer/dryer are available for your use as well as high-speed Wi-Fi. An office space is available for those that work from home. Quiet area with much wildlife to enjoy around the house!

Top guest favorite
Snow-capped peaks of Mt Katahdin are visible in the distance, framed by a diverse landscape of trees. The foreground features a mix of leafless branches and evergreen trees, while the sky is clear with soft blue hues.
Vacation home in Stacyville
4.98 out of 5 average rating, 101 reviews

Baxters place in the shadows of Mt Katahdin .

A place for adventure in the shadows of Mt Katahdin. Located on a quiet dead end road with many Amish people and horses . The whole group will be comfortable in this spacious and unique space. Baxter park, Katahdin woods and waters national monument, hiking, biking and white water rafting nearby. ATV and snowmobile from here on fantastic statewide trail system. Groceries, restaurant and fuel 5 minutes away. Shin pond 30 miles-Milli Houlton, Lincoln 45 miles- Bangor 85 miles.

Guest favorite
Tiny home in Bangor
4.85 out of 5 average rating, 156 reviews

Field of Dreams Tiny Home

Cozy Tiny Home with Stunning Views Escape the hustle and bustle in this charming tiny home with serene field views. Enjoy the tranquility of nature while still being conveniently located just minutes from Bangor's airport and town center. Relax and unwind in the private Jacuzzi with stunning views of the endless field or gather around the fire pit for a cozy evening under the stars. The projector screen offers endless entertainment options, perfect for movie nights or gaming.

Popular amenities for Winn vacation rentals

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