Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

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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, 122 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, 396 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, 115 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, 160 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.

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, 168 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, 107 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, 145 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.

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

Apartment in Bangor

4.9 out of 5 average rating, 161 reviews

Historic Hotel|West Market Square

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, and drinks!

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, 241 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

Top guest favorite

A comfortable living space is featured with two large windows allowing natural light to brighten the room. A cozy sofa with red cushions sits adjacent to a chair, while a wooden table is positioned nearby. A floor lamp provides additional lighting.

Guest suite in Stockton Springs

4.97 out of 5 average rating, 168 reviews

Penobscot River Views - Two Room Suite!

Two room suite on the first floor of my home with an en-suite private bathroom and views of the Penobscot River/Bay! ***Just under an hour drive to Acadia.*** Convenient access right on Route 1. A short walk to the Sandy Point beach park. Comfortable queen bed and sleep sofa. Two 40” HD TVs with Roku. Mini fridge, microwave, toaster oven and induction burner in room. Almost 400 SF of space! If you need more beds, please see my listing for the room upstairs.