Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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

Cozy Cottage on the Penobscot – Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

LocationFamilyDecor

5.0 out of 5 average rating, 163 reviews

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

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.

LocationFamilyIndoor spaces

4.9 out of 5 average rating, 135 reviews

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

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.

FamilyLocationParks

5.0 out of 5 average rating, 125 reviews

Guest favorite

The historic home features a classic two-story facade with white siding and black accents. A large entryway with double doors is framed by a well-maintained garden, showcasing vibrant purple flowers in the foreground. Sunlight filters through the trees, casting gentle shadows on the lawn.

Apartment in Winterport

Cozy 1st Floor Studio - 1812 Pierce House

1812 Pierce House is a unique home on the National Register of Historic Places. Full of antiques & modern touches. If you like interesting places to stay, this is for you! If you like straight lines & central air, we recommend a hotel. A private entrance with your own entry hall bedroom w/ table, closet, & small hall leading to the bathroom w/ shower. Small fridge with freezer, hot water kettle, coffee/tea, 2 electric burners, toaster & microwave. Firepit in large yard. Close walk to river.

FamilyLocationAccuracy

4.88 out of 5 average rating, 101 reviews

Guest favorite

The rustic lodge is surrounded by lush greenery, featuring a unique tower and a welcoming entrance. The exterior showcases wood shingles and large windows, inviting natural light. Flowering bushes in the foreground add a touch of greenery to the charming facade.

Home in Frankfort

Relaxing lodge in the woods

Rustic lodge nestled in the woods, on 60+ acres. Close to Bangor, coastline, and 50 miles to Bar Harbor. Large eat in dining area with plenty of room for family and friends. Outdoor fields for games, grilling, access to Maine wildlife, with plenty of parking. Private master bedroom w/bath. Large community areas to enjoy time with friends and family. At night spend time by the campfire and take in the stunning night sky. Party and events are not allowed at this time due to COVID-19 policies.

ValueFamilyLaundry

4.94 out of 5 average rating, 178 reviews

Top guest favorite

The cabin exterior features a charming combination of wood siding and dark paint, with a covered porch inviting relaxation. A small table with two chairs is positioned on the deck, overlooking a landscaped area with gravel and plants. Large windows provide natural light to the interior.

Cabin in Frankfort

Streamside Cabin at Trailhead

Enjoy some peace and quiet at this stream side cabin. This stylish little cabin is tucked away at the end of a quiet, dead end road. It is also located just steps away from historic Mount Waldo. Hike up the mountain to see beautiful vistas and a granite quarry. Put in a canoe or kayak at the public boat launch right down the road! Centrally located for travel to many coastal towns and beaches. Right off from scenic Route 1A. One hour away from Acadia National Park.

FamilyValueComfort

4.98 out of 5 average rating, 102 reviews

Top guest favorite

Home in Hampden

Cape house in Hampden

Keep it simple at this peaceful and centrally-located place. Short drive to concerts, shopping, hospitals, skiing, the coast- you name it! It's all just a short drive away. This adorable cape sits on one acre of beautiful land, complete with fruit trees and gorgeous flowers. The house, built in 1910, has the character of an old house, but was recently lovingly restored. The original wide pine floors can still be found in the two bedrooms on the second floor.

ValueLocationBreakfast

4.86 out of 5 average rating, 111 reviews

Top guest favorite

The main living space features a modern kitchen with light wood cabinetry and dark appliances. A dining table sits center, surrounded by chairs. Large windows provide an abundance of natural light, while a cozy seating area invites relaxation. A wood stove is present for warmth during colder months.

Cabin in Jackson

Forest Cabin w/ Stunning Wall of Windows

Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

LocationFamilyLayout

4.99 out of 5 average rating, 221 reviews

Top guest favorite

A modern kitchen area features gray cabinetry and a wooden countertop. Above, shelves hold neatly arranged dishes and mugs. The space is illuminated by overhead lighting, highlighting fresh flowers beside a coffee maker. A sink with a modern faucet is centrally located, enhancing functionality.

Cottage in Hampden

MaineStay Cottage #3 Full Kitchen Hampden/Bangor

NEWLY RENOVATED from top to bottom! MaineStay Cottage #3 highlights a modern farmhouse theme with touches of Maine blueberries throughout! Featuring brand new stainless steal appliances, a fully stocked kitchen, an electric fireplace, new ultra comfort bedding, fresh linens, a smart TV for streaming your favorite shows, with a charming dining area for 2, and everything you’d need for a relaxing stay - you can’t go wrong!

ValueLocationBathroom

4.97 out of 5 average rating, 377 reviews

Top guest favorite

Home in Winterport

Fall in Maine/Waterview/Firepit/Sleeps 12

Nestled in the woods with beautiful views of the Penobscot River, Two Cottages on the River sleeps comfortably up to 12 guests and offers the perfect balance of peaceful seclusion and coastal adventure. Enjoy easy scenic drives to favorite seaside destinations such as Camden, Rockport, Belfast, Bar Harbor, Stonington, and Acadia National Park, then return home to unwind away from the crowds and tourist bustle.

FamilyLocationHospitality

5.0 out of 5 average rating, 18 reviews

Superhost

Tiny home in Winterport

Timberlight Retreat | Tiny Home Cabin

Enjoy Timberlight Retreat, a tiny home with a queen bed, fully equipped kitchen, spa-style shower, and built-in projector with Google TV. Look out from your large picture window with forest views. Relax in your private outdoor hot tub, unwind in the quiet woods, and take advantage of easy access to trails, lakes, and local dining. Ideal for couples, weekend getaways, or a nature escape.

LocationFamilyHiking

4.84 out of 5 average rating, 38 reviews

Top guest favorite

A charming cottage is surrounded by vibrant flowers and greenery. The front porch, featuring traditional wooden railings, invites relaxation. Soft sunlight filters through the trees, illuminating the cottage's exterior, while a wooden fence frames the yard, adding to the peaceful ambiance.

Cottage in Winterport

Cozy cottage in Winterport Village

This peaceful cottage is nestled in a small village situated halfway between Belfast and Bangor along the Penobscot River. You’ll find yourself just far enough “off the beaten path” while still in a quaint neighborhood with lots of history. An easy starting point when planning a trip to Midcoast or Downeast Maine, and to the lakes and mountains in the north and west.

FamilyValueTV

4.99 out of 5 average rating, 108 reviews