
Holiday houses in Winterport
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Top-rated holiday rentals in Winterport
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Sail Loft
Just 1 hour from Acadia National Park, "Mayor's Mansion", home to Ralph Johnson, the first Mayor of Belfast and William V Pratt, Chief of Naval Operations during the Depression. Built in 1812 just as the war of 1812 was beginning, this historic Greek Revival is located in the center of Belfast Maine sited along the waters of Penboscot Bay. 2 min walk to the downtown square. 2 bedrooms and 2.5 baths with full kitchen, washer/dryer, and desk for work. No parties that could cause damage or a mess

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!

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 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.

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

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.

Whitetail by the River, Acadia National Park 10m
Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Lake Front-Spa Tub-Fire Pit-Full Kitchen-Canoe
Need to escape the hustle and bustle or a cramped work from home life? The year-round lakehouse is perfect for the outdoor recreational enthusiast, the work-from-home adventurist, a family trip to Acadia, or a cold-weather spa escape. Enjoy this spacious waterfront home in Bucksport, Maine. Relax in the spa tub, fish from the included canoe and kayak, or work remotely with a view. When you want to explore, the home's location is convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Belfast Harbor Loft
Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Luxury Coastal Maine 2BR Apt, 2nd Fl Stunning View
The entire building was completely and structurally remodeled and everything is new. Each unit has new floors, walls, lighting, HVAC, kitchens, bathrooms, bedrooms, and brand new mid-century modern furniture throughout. These are truly designed and built as luxury short term rental units. It's location is perfect to explore greater Penobscot Bay region, Acadia National Park, and it sits in the heart of mid-coast Maine. It is beautiful, friendly, and a perfect place to be.

Quiet lakefront cottage on Graham Lake
Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets
Popular amenities for Winterport holiday rentals
Other great holiday rentals in Winterport

The Colby House - Built in 2025!

Dickey's Bluff Lakeside Cottage

Cozy Lakefront Cabin * CampChamp

Bucksport oasis, w/hot tub! One hour to Acadia NP!

The Swan Lake House - Lakefront-Private Beach

Home in Bangor | Private Yard

Small cabin with 5 acres.

The Cubby
Frequently Asked Questions
How much does it cost to stay in house rentals in Winterport?
Experience the best of Winterport with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winterport have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Winterport. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Winterport?
Yes! Work meets play with ease at over 10 house rentals in Winterport featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Winterport?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly house rentals in Winterport?
Four-legged friends are welcome in Winterport. Choose from more than 10 house rentals for guests traveling with pets.
Do house rentals in Winterport have wifi?
Absolutely! We offer over 20 house rentals with wifi in Winterport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winterport have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Winterport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winterport?
Winterport has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Winterport

Total holiday rentals
Explore 50 holiday rentals in Winterport

Nightly prices starting at
Winterport holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 1,920 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Winterport holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Dragonfly Farm & Winery
- Sandy Point Beach
- Sand Beach
- Bear Island Beach
- Lighthouse Beach
- The Camden Snow Bowl
- Eaton Mountain Ski Resort
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Farnsworth Art Museum
- Rockland Breakwater Light
- Narrow Place Beach
- Islesboro Town Beach
- North Point Beach
- Three Island Beach
- Driftwood Beach
- Pebble Beach
- Billys Shore
- Hero Beach




