
House holiday rentals in Winterport
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Top-rated house rentals in Winterport
Guests agree: these houses are highly rated for location, cleanliness and more.

Cute Midcoast Cottage w Hot Tub
Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

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

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 12 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.

Come relax in our cozy and fresh home!
Welcome to a newly renovated two bedroom and 1 bathroom home in a welcoming residential neighborhood. Our home has an open layout w/ a spacious deck and yard off the back of the house and an attached garage. We welcome children and families. This space is centrally located to the shopping areas; 5-10 minutes by car, we are also quite close to the eclectic downtown. Downtown Bangor is a quick 10 minute drive or if you enjoy walking approximately 30-35 minutes through the lovely ‘tree’ streets.

Maine Wilderness Oasis: Hike Swim Kayak Fish
Take it easy at this unique getaway. Spend your days hiking the backyard trails (25 acres behind the house!), swimming or paddle boarding on the lake with a private dock (lake is a 2 minute walk down the driveway!), or traveling to near by coastal towns like Bar Harbor (Bucksport was voted #1 small coastal town in USA!). For dinner, stop by one of the lobster shacks just down the road to bring home your fresh Maine lobster! Come and disconnect (or stay connected if you’re working remotely!).

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.

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.

Waterfront-40min to Acadia-Main House-Fire Place
Enjoy all four of Maine's seasons at this lakehouse. The Main House at Getogether Stays cabin micro-resort sleeps 8 and includes free kayaks. Have you ever dreamed of being the owner of a campground or wondered what it is like to stay in the owner's building at one? Well here is your chance to live your dream for a visit to this cabin campground. The cabins are closed in the winter, but the main house is still available to rent! Enjoy this lovely home and the entire grounds of the property

Close to Restaurants, Acadia, Casino, Concerts!
Your family will be close to everything when you stay at this centrally-located home. Distances- .9 miles to Maine Savings Amphitheater 42 miles to Acadia. This home is within walking distance to the casino, the Cross Center, a seafood market, Paul Bunyan statue, and several restaurants. The highway is easily accessible. The home has 4 bedrooms(one designed to be primarily for children), one with a king bed, and two with queens. Also, the living room sectional has a pull out bed.

Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

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.
Popular amenities for house rentals in Winterport
House rentals with a pool

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

Luxe Liberty: Getaway with Heated Indoor Pool!

Coastal Retreat with Pool and Cheerful Vibes

The Jarvis Homestead | Historic Maine Mansion

New Boho Cape with Pool! Fenced yard, pet friendly

House in the woods

Dog Friendly Midcoast Cape

Ocean View Retreat with Heated Pool / Hot Tub
Weekly house rentals

The Colby House - Built in 2025!

Belfast Oceanside House - on downtown harbor walk

Sunset Retreat on Brewer Lake

Cozy Retreat Near Lake-60mins to Acadia

The Swan Lake House - Lakefront-Private Beach

Home in Bangor | Private Yard

Middle of Everywhere - 4 BR!

Tides' Reach - Private Waterfront King Beds
Private house rentals

River Apt by UMaine

Spacious 3BR Home in Bangor!

#1 NE Small Coastal Town- Castine, Shell Cottage

Sunset Cove on Swan Lake - Stunning Lake Views!

Mill Stream Cottage

Delight<Farmhouse

Cozy Stay in Bucksport

Fall & winter retreat on Crockett Cove
Quick stats about house rentals in Winterport

Total holiday rentals
Explore 20 holiday rentals in Winterport

Nightly prices starting at
Winterport holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Winterport holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winterport rentals

4.8 Average rating
Winterport stays are highly rated by guests – averaging 4.8 out of 5!
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- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Hermon Mountain Ski Area
- Sandy Point Beach
- Dragonfly Farm & Winery
- Sand Beach
- Bear Island Beach
- Lighthouse Beach
- Eaton Mountain Ski Resort
- The Camden Snow Bowl
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Farnsworth Art Museum
- Narrow Place Beach
- Rockland Breakwater Light
- Three Island Beach
- Islesboro Town Beach
- Driftwood Beach
- North Point Beach
- Hero Beach
- Billys Shore
- Pinnacle Park




