Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

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Guest favorite

A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.

Cottage in Hermon

4.91 out of 5 average rating, 117 reviews

Lakefront Cottage on Tracy Pond, New Hampshire

Lakefront private cottage right on 47 acre Tracy pond. This pond has no public access so it is very quiet with only my home and another Air BnB rental on the 25 acre parcel. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

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, 106 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, 92 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, 145 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 cozy sitting area features a gray couch adorned with soft pillows. A wooden coffee table rests on a textured rug, accompanied by a small plant. A wall clock and a mounted TV are visible, enhancing the bright, inviting atmosphere.

Cottage in Hampden

4.93 out of 5 average rating, 285 reviews

Central MaineStay Cottage2 Hampden/Bangor

Welcome to the all NEW cottage #2! As of 12/14/21 this cottage has been completely renovated from the ground up - literally even new floors + ceiling. This cottage features a cozy space perfect for two. A new couch, rug, fireplace, and TV ready to stream all your favorite shows makes for the perfect night in. While you’re with us enjoy the all new fully stocked kitchen & dining area. Let’s not forget the queen sized Serta mattress and fresh linens. You can’t go wrong with this cozy cottage!

Top guest favorite

A spacious bathroom features a freestanding soaking tub with elegant gold feet. A large window allows natural light to illuminate the space. Decorative plants and a stylish mirror add a touch of greenery and style, while wooden accents provide a rustic charm.

Guesthouse in Orrington

4.97 out of 5 average rating, 158 reviews

Spa-themed bedroom loft in 1850s farmhouse

PLEASE READ full listing BEFORE booking. La Petite Ferme is a mid-19th century farm located 8 miles from Bangor airport, 4 miles from the amphitheater and an hour's drive to Acadia. Enjoy a spa-themed loft in a stylish, upstairs room with ensuite bathroom and private use staircase for a contactless stay. Spend the night stargazing through the cathedral ceiling's sky lights, or listen to some vinyl while you get creative with the art supplies! Perfect for a romantic getaway or personal retreat.

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, 98 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

Guest favorite

A welcoming living area is portrayed, featuring a brown leather sofa adorned with a decorative cushion. A clear glass table is set with a delicate lace doily and a small vase of yellow roses. Near the window, a vintage record player adds a touch of charm to the space.

Apartment in Bangor

4.86 out of 5 average rating, 168 reviews

Historical Hideaway/In-Town

CharmHouse Historical Hideaway is a cozy one-bedroom first floor apartment in a very quiet neighborhood in the heart of Bangor. Perfect for a couple or traveling professional. There is one unit upstairs and a backyard unit with a long-term family residing. We have created a space that will welcome you home after a long day at the coast, downtown shopping and dining or workday. Our property is within a walk to downtown and close to both local hospitals for those wanting to travel and work.

Top guest favorite

A calm river scene is depicted, showcasing smooth water reflecting a clear blue sky. Lush green grass lines the riverbank, while trees provide gentle shade in the foreground. Rolling hills and a distant shoreline complete the serene view, enhancing the tranquil setting.

Guesthouse in Prospect

4.97 out of 5 average rating, 133 reviews

The Penobscot River Ranch Guesthouse

This unique four season property sits across from conservation land on the Penobscot River in Prospect Maine. There is a 1/2 mile trail down to the river, great for hiking and snowshoeing. An awesome place to unwind with easy access for exploring mid coast and Downeast Maine. Less than 10 minutes to Rt 1 and The Penobscot Narrows Bridge and Rt 1A, 18 miles to Belfast, Castine, Blue Hill, Ellsworth. About an hour to Acadia NP and 45 min to Bangor. Great views of the land, river and wildlife.

Superhost

The cozy bedroom features a spacious bed with a light-colored quilt and a bedside lamp. A small basket is placed nearby, and a window with patterned curtains allows natural light into the room. A wall-mounted air conditioning unit is visible.

Apartment in Brewer

4.8 out of 5 average rating, 166 reviews

Lovely- 1 bedroom rental with shared outdoor space

Our one bedroom apartment is multilevel with a large shared out door space. Eat outside on the large deck, or relax by the fire pit. Spend your days shopping in Bangor, exploring Acadia National Park, Penobscot Observatory, and many more wonders of our great state. At night, relax in the AC and put on your favorite show. Start each day with free coffee. Our apartment has all you need to enjoy your stay! *Stairs on property are relatively steep. First floor bathroom, second floor bedroom*

Guest favorite

A spacious studio room features tall windows with sheer drapes, allowing natural light to fill the space. A king-sized bed with crisp linens is centered, complemented by a stylish armchair and a small table. A wall-mounted TV and a mirror enhance the contemporary decor.

Apartment in Bangor

4.9 out of 5 average rating, 125 reviews

King Bed|Market Square View|DTWN Bangor

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 w/ high end Centium Satin linens ☀ 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 cozy bedroom features a king-sized bed with a textured blue coverlet and accent pillows. Two windows provide natural light, while decorative lamps sit atop the bed's headboard. A fan is positioned nearby, and a vibrant orange door adds a pop of color.

Home in Brooks

4.98 out of 5 average rating, 101 reviews

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.