
Vacation rentals in Winterport
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Top-rated vacation rentals in Winterport
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Lakefront Log Cabin on Pleasant Lake
Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

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.

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.

Waterfront Cottage
Cozy Two-Bedroom Apartment on Hermon Pond, Hermon, Maine Enjoy a charming two-bedroom apartment attached to our home, just 5 minutes from the interstate, 20 minutes from Bangor International Airport, and about an hour from Acadia National Park. With our long private driveway and the serene pond in the backyard, you’ll feel like you’re in the middle of nowhere. Recently remodeled, the apartment exudes a cozy camp vibe with wide yellow pine walls, hidden doors, and beautiful views of the lake.

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.

Bangor Waterfront Area Home. Large 1BR 1.5 Bath
Spacious, comfortable and fully equipped 2nd Floor 1 BR 1.5 BA in town apartment. Super convenient location is easy walking distance to the waterfront park, supermarket and everything downtown. It includes a nice outdoor deck with a view of the river and off street parking for 1 car. Owner/host occupied building. Located 10 minutes from BGR / Bangor airport, 5 minutes from I-95, 1 hour to Bar Harbor/Acadia National Park. Shaws supermarket and Dunkin’ are next door. 3 hospitals are nearby.

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 stunning 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!

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.

The Loft. A Midcoast Maine Home Base.
A perfect place to use as your base for exploring Midcoast Maine. We are 8 miles from Camden or Rockland. 34 miles from Boothbay Harbor and 90 miles from Bar Harbor. This is your home away from home. A fully stocked kitchen, ready for meals after a long day of exploring. We have 1.5 baths, a washer and dryer and three Smart Tv’s. This 1700 sq foot warehouse loft has central air conditioning, two bedrooms and a large living space.
Popular amenities for Winterport vacation rentals
Other great vacation rentals in Winterport

Oceanfront Rockport Cottage #6 - Oakland Seashore

Etna pond retreat

Cottage by the Pines Near Swan Lake and Belfast

*NEW* Bagaduce River Cottage @ Old Hart Farm

Home in Bangor | Private Yard

New | Riverside | Fire Pit 3BR 2.5 bath

Antique Coastal Maine Cape

Loon Sound Forest Cottage
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- Acadia National Park
- Acadia National Park Pond
- The Camden Snow Bowl
- Sand Beach
- Farnsworth Art Museum
- University of Maine
- Rockland Breakwater Light
- Maine Discovery Museum
- Bass Harbor Head Light Station
- Schoodic Peninsula
- Moose Point State Park
- Maine Lighthouse Museum
- Cellardoor Winery
- Hollywood Slots Hotel & Raceway
- Camden Hills State Park




