Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

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Guest favorite
A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.
Cottage in Hermon
4.91 out of 5 average rating, 137 reviews

Lakefront Cottage on Tracy Pond

Lakefront private cottage right on 47 acre Tracy pond. This pond has no public access so it is very quiet with only my home and another Air BnB rental on the 25 acre parcel. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

Top guest favorite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.95 out of 5 average rating, 211 reviews

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

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 404 reviews

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.

Top guest favorite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 124 reviews

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

Superhost
A living room is depicted with a light-colored sofa, flanked by two patterned armchairs. A wooden coffee table occupies the center, and a textured area rug is laid beneath. Natural light enters through sheer curtains, while wall art and a lamp enhance the cozy ambiance.
Home in Winterport
4.88 out of 5 average rating, 112 reviews

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.

Top guest favorite
A comfortable living space is complemented by large windows offering expansive views of the surrounding countryside. A gas fireplace adds warmth, and a ceiling fan provides airflow. The seating includes a leather chair and a sofa adorned with decorative pillows, set over a soft area rug.
Guesthouse in Winterport
5 out of 5 average rating, 113 reviews

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

Guest favorite
The rustic lodge is surrounded by lush greenery, featuring a unique tower and a welcoming entrance. The exterior showcases wood shingles and large windows, inviting natural light. Flowering bushes in the foreground add a touch of greenery to the charming facade.
Home in Frankfort
4.94 out of 5 average rating, 173 reviews

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.

Top guest favorite
A fire pit is set beside the calm waters of Long Pond, reflecting the soft colors of the evening sky. Surrounding trees create a natural frame, enhancing the serene atmosphere of this waterfront location.
Cottage in Bucksport
4.92 out of 5 average rating, 247 reviews

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!

Top guest favorite
A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.
Guesthouse in Orland
4.99 out of 5 average rating, 182 reviews

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 400 Mbs cable 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. Pet friendly!

Top guest favorite
A view from a shaded patio showcases a round table surrounded by wicker chairs. The lush green lawn extends to the water's edge, where trees provide a natural frame for the serene expanse of the bay, dotted with clouds reflecting in the distance.
Home in Belfast
4.92 out of 5 average rating, 184 reviews

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.

Top guest favorite
The cabin exterior is softly illuminated by string lights, enhancing the porch area. A cozy seating arrangement is visible, complemented by a wooden railing and steps leading to the yard. Surrounding trees provide a natural backdrop under the twilight sky.
Cottage in Bucksport
4.98 out of 5 average rating, 161 reviews

Cozy Cottage in the Woods

Our open concept 2 bedroom home nestled in the woods has the charm of a cottage but the comforts of home. Morning coffee on the porch is often accompanied by sightings of deer in the large field out the front door and hummingbirds busy at the feeder. Get away from it all while being only 25 min from Bangor, under an hour from Belfast & Camden, and 45 min to an hour from Acadia & Bar Harbor!

Top guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham
4.95 out of 5 average rating, 841 reviews

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 vacation rentals

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 vacation rentals in Winterport

  • Total vacation rentals

    Explore 50 vacation rentals in Winterport

  • Nightly prices starting at

    Winterport vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 1,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winterport vacation rentals include wi-fi 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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