Holiday rentals in Winterport

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 800 Mbs fiber 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. We’re very pet friendly!

Nomad's Rest-Secluded Modern Camp 30 miles to MDI

The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures. Adults-only and not equipped to handle children or infants

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

The Greenhouse Cottage

We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

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.

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

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.

Acadia Region New Oceanfront Cottage

Relax and unwind at this unique waterfront retreat where you can enjoy breathtaking views of the ever-changing tides. Keep an eye out for bald eagles, osprey, and the occasional seal as you soak in the natural beauty around you. This renovated former boathouse combines comfort with convenience, offering the perfect base for your coastal adventures. Situated in Mid Coast, Maine, it's ideally located just an hour from Acadia National Park, 15 minutes from Belfast, and 45 minutes from Camden.

Lavender by the Sea

The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

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.

Acadia Pines Cabin w/HotTub 10min2Downtown

Welcome to Acadia Pines Retreat, where the whispering pines and peaceful forest trails set the tone for your perfect Maine escape. Nestled just a short drive from Acadia National Park and the coast, this charming retreat offers the serenity of the woods with the comforts of home. * Peaceful, secluded location *Private hot spa jacuzzi to soak in after a day of hiking *Outdoor seating and stargazing spots 📍 Centrally located for day trips, lobster shacks, and scenic drives

Forest Cabin with 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!