Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

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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, 208 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

Guest favorite

The open concept living area features a comfortable sectional sofa and armchairs arranged around a round coffee table. A brick fireplace is positioned near the flat-screen TV. Modern appliances are visible in the kitchen area, with overhead lighting enhancing the space.

Apartment in Bucksport

4.94 out of 5 average rating, 125 reviews

Luxury Coastal Maine Apartment 1st Floor

Nestled in the charming coastal village of Bucksport, this luxury two bedroom, one bathroom apartment has everything you need to feel comfortable away from home. A short half-block walk takes you to Main Street restaurants, shops, and a beautiful waterfront walkway. Just 35 miles away, Acadia National Park is an easy day trip. Twenty miles from Bangor, Belfast, and Ellsworth, this lovely little town is centrally located for vacation or business travel. Close to Maine Maritime Academy and UMaine.

Guest favorite

The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.

Treehouse in Appleton

4.97 out of 5 average rating, 399 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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, 116 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.

Guest favorite

A living room is depicted with a light-colored sofa, flanked by two patterned armchairs. A wooden coffee table occupies the center, and a textured area rug is laid beneath. Natural light enters through sheer curtains, while wall art and a lamp enhance the cozy ambiance.

Home in Winterport

4.89 out of 5 average rating, 102 reviews

Hidden Gem

This recently renovated home is located in the heart of historic Winterport, Maine. It’s located on a quiet street with views of the Penobscot River. Winterport is an old fashion, quaint town, where everyone is very friendly. The home has three bedrooms and one bath with plenty of room to spread out. This house is so centrally located its only 52 miles to Bar Harbor and Acadia National Park, 21 miles to Belfast and 40 miles to Camden just to name a few of the beautiful coastal towns in Maine.

Top guest favorite

The modern kitchen and living area feature light wood ceilings and ample natural light from large windows. A comfortable sectional sofa and a wooden dining table are complemented by sleek cabinetry and appliances, creating a warm and inviting gathering space.

Cabin in Jackson

4.99 out of 5 average rating, 163 reviews

Wall of Windows - Super Clean & Solar-powered

This newly constructed 850 sq ft cabin features a wall of windows and is located on a 30 acre forest. It is perfect for those seeking a peaceful and cozy space to relax and breathe deeper while experiencing the brilliance of Mid-Coast Maine. Wake up to the gentle morning sun cresting over the trees, linger at night under the magic and mystery of a star-filled sky, and witness what all four seasons have to offer. Belfast and Unity are close w/ Bangor, Camden, Rockland, & Acadia - easy day trips.

Guest favorite

A rustic interior is visible, showcasing warm wood finishes and natural light. A dining table and chairs sit in the screened-in porch area, surrounded by greenery. The doorway leads to a cozy sleeping area, emphasizing the home's connection with nature.

Tiny home in Jackson

4.87 out of 5 average rating, 263 reviews

Tiny House oasis in Beautiful Waldo County. We❤️🐕

We have an adorable rustic & comfy tiny house; warm & cozy, with a big queen bed & AC. LAST MINUTE DISCOUNT September 7th through 11th. Check it out! There is a fridge, tea kettle, toaster oven & stovetop. Try our new outdoor shower building. There's a composting toilet indoors which works well & smells not at all. NO INDOOR PLUMBING but we supply drinking/cooking/washing water & there is a sink that drains. If you have more people & your own camping equipment, look for our other listing.

Top guest favorite

A comfortable living space is complemented by large windows offering expansive views of the surrounding countryside. A gas fireplace adds warmth, and a ceiling fan provides airflow. The seating includes a leather chair and a sofa adorned with decorative pillows, set over a soft area rug.

Guesthouse in Winterport

5 out of 5 average rating, 109 reviews

Winterport Evergreen Farm - Guest House

Relax & enjoy a private, peaceful stay at this beautiful Christmas tree farm in Winterport. We offer the perfect spot for nature lovers and couples! Conveniently located 20 minutes from both Bangor and Belfast and 75+/- mins from Acadia National Park. After a day of adventuring on or off the property, unwind around the fire pit or on your deck. This property has woodland trails that cover 200+ acres that includes a pristine farm pond. Couples who love cooking will relish the appointed kitchen

Top guest favorite

Tiny home in Surry

4.96 out of 5 average rating, 149 reviews

Tiny House at Wooded Bliss Homestead

On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

Guest favorite

A spacious room features a king-sized bed with a wooden frame, a round mirror above a dark dresser, and large windows draped with dark curtains. A comfortable chair and small tables are positioned nearby, while hardwood flooring adds warmth to the space.

Apartment in Bangor

4.91 out of 5 average rating, 220 reviews

Historic Hotel|King Bed|Steps to great Food&Drink

1873 historic hotel that sits in the heart of downtown Bangor. Just steps from fantastic restaurants, breweries, & coffee shops! 1/2 mi. to Amphitheater *10 minute walk* 43 mi. to Acadia Nat'l Park 3 mi. to airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ King-sized bed; premium front facing Market Square View ☀ High Speed Fiber Internet ☀ 50” Roku TV w/ HULU + ☀ Desk ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

Top guest favorite

A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.

Guesthouse in Orland

4.99 out of 5 average rating, 175 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Guest favorite

A spacious kitchen is highlighted by modern appliances and a large island with seating. Bright yellow doors add a pop of color to the minimalist design, while an adjacent living area offers comfortable seating. The layout extends to a well-lit corridor lined with framed artwork.

Loft in Bangor

4.95 out of 5 average rating, 244 reviews

The Downtown Loft Bangor

Not just another AirBnB "hotel"! A historic building, the Loft has been fully renovated with a modern, minimalist vibe. Your private escape in the heart of downtown Bangor. Comfy king bed, luxury bath, chef's kitchen, top -rated king sofa bed, and massive windows that open to an expansive view of Main Street! 0.0 miles to all things Downtown Bangor 0.5 miles to Waterfront Concerts 0.9 miles to Hollywood Slots 1.0 miles to Cross Insurance Center 1.2 miles to Eastern Maine Medical