
Holiday rentals in Winterport
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Top-rated holiday rentals in Winterport
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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!

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

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

Lakefront Gem with Breathtaking Island Views
You didn’t know you needed this- until you arrived. A modern studio tucked right on the water’s edge, where nothing is between you and the lake but loons, sunlight, and a whole lot of time to just be. Private dock (float, fish, float again) Spa-style indoor + outdoor showers (yes, both. Why not?) Outdoor movie night under a blanket of stars Pet-friendly Swimming, stargazing, and stories you’ll be telling next year Just a short drive from town or Acadia — if you ever want to leave.

Belfast Harbor Loft | Downtown
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.

King Bed|DTWN|Fiber Internet|Steps to Food&Drink
1873 historic hotel that sits in the heart of downtown Bangor. Just steps from fantastic restaurants, breweries, & coffee shops! 1/2 mi. to Amphitheater *10 minute walk* 43 mi. to Acadia Nat'l Park 3 mi. to Airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ King-sized bed w/ high end Centium Satin linens ☀ High Speed Fiber Internet ☀ 50” Roku TV w/ HULU + ☀ Desk ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

LOFTY-DIGS
Lofty-Digs is a newly constructed studio apartment in the upstairs of our barn. We are delighted to tell you that we are solar powered!!! The apartment offers a private entrance, small balcony overlooking our garden, free off street parking, a full bath, plenty of closet space all in a peaceful inviting, quiet, and roomy studio. Walking distance to all that Bangor has to offer including Waterfront Pavilion, Stephen King's house, wonderful pubs and restaurants.

The Reach Retreat
Coastal, light and airy, this studio is perfect for those seeking to explore all that Deer Isle has to offer! Located on the Eggemoggin Reach, you will have access to hiking trails, kayaking, sailing, shopping, and lobsters from the lobster capital of the world, Stonington! We are so lucky to live on this beautiful island and are looking forward to sharing a piece of our paradise with you!

MaineStay Cottage #5 Full Kitchen Hampden/Bangor
Welcome to MaineStay Cottage #5 highlighting a bright and airy living space with unique Maine touches throughout. Featuring a remodeled fully stocked kitchen, an electric fireplace, a smart TV for streaming your favorite shows, with a charming dining area for 2, a comfortable queen size bed, and everything you’d need for a relaxing stay - you can’t go wrong!

BANGOR MAINE ENTIRE HOUSE QUIET NEIGHBORHOOD
COME AND ENJOY A WONDERFUL STAY IN THIS QUIET NEIGHBORHOOD!! TWO BEDROOM 1 BATH HOME WITH A 3 SEASON PORCH AND A NICE LARGE DECK IN THE BACK. NEWLY RENOVATED BATHROOM AND KITCHEN. THIS HOME CENTRAL TOO ACADIA NATIONAL PARK AND MOUNT KATAHDIN, WALKING DISTANCE FROM DOWNTOWN AND APPROXIMATELY 1 MILE FROM THE AIRPORT.
Popular amenities for Winterport holiday rentals
Other great holiday rentals in Winterport

Peaceful 3BR Home w/ Barn on Expansive Acre

Peaceful historic 1855 farmhouse

Residential Brewer apt close to shopping and work

Coastal Retreat • Spa Bath • Forest Privacy

Home in Bangor | Private Yard

423 French

Swazey Carriage House

Peaceful Coastal Oasis
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 vacation rentals with a dedicated workspace in Winterport?
Yes! Work meets play with ease at over 10 vacation 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 10 homes with a kitchen, over 10 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Winterport?
Four-legged friends are welcome in Winterport. Choose from more than 20 vacation 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 vacation rentals in Winterport?
Winterport has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Acadia National Park
- Acadia National Park Pond
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- Sand Beach
- Farnsworth Art Museum
- Rockland Breakwater Light
- University of Maine
- Cellardoor Winery
- Schoodic Peninsula
- Moose Point State Park
- Cold Stream Pond
- Camden Hills State Park
- Maine Discovery Museum
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- Maine Lighthouse Museum
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