Holiday rentals in Winterport

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

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.

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.

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

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.

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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

A-Frame Getaway | Hot Tub | Pool Table

Escape to this 1970’s A-frame tucked into the woods of Winterport, Maine. Thoughtfully updated while keeping its original charm, the home feels warm, cozy, and relaxed. The two bedrooms are upstairs in the loft and accessed by steep, traditional A-frame stairs. Downstairs features a casual hangout space with a pool table. Step onto the deck to enjoy the private hot tub, plus the convenience of an in-home washer and dryer.

Modern Cabin in the Pines • Hot Tub + Near Acadia

Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

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.

Waterview-Deck-Firepit-Visit Acadia/Bar Harbor

Nestled in the woods with beautiful views of the Penobscot River, Cottage on the Cove 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.

Field of Dreams Tiny Home

Escape to our charming tiny home near Bangor, a perfect retreat for 2. Enjoy serene field views from a panoramic window, a private hot tub, and a cozy fire pit. Inside, a modern wood-paneled interior with a projector screen for movie nights awaits. This unique stay offers tranquility and modern comfort, just minutes from the city.