Vacation rentals in Winterport

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Top-rated vacation rentals in Winterport

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Bucksport

4.92 out of 5 average rating, 279 reviews

Chateau Chouinard Acadia NP & MMA, pets okay!

Contactless entry. Central location between Belfast, Bangor and Ellsworth. Close to Fort Knox and the Bucksport river walk, schools, restaurants and the business district. Just 50 minutes to Acadia National Park. Our casual, clean environment can be a place for you to relax and enjoy your stay in mid coast Maine at the gateway to the down east. There is a heat pump providing both heat and air conditioning, fireplace and outdoor firepit. Full kitchen with spices and breakfast items included.

Dec 2 – 9

G$33,404 GYD per night

Guest favorite

Guesthouse in Orrington

4.97 out of 5 average rating, 117 reviews

Spa-themed bedroom loft in 1850s farmhouse

PLEASE READ BEFORE BOOKING: Welcome to "La Petite Ferme," a mid-19th century farm located 8 miles from Bangor airport, 4 miles from the amphitheater and an hour's drive to Acadia. Enjoy a spa-themed loft in a stylish, upstairs room with ensuite bathroom and private use staircase for a contactless stay. Spend the night stargazing through the cathedral ceiling's sky lights, or listen to some vinyl while you get creative with the art supplies! Perfect for a romantic getaway or personal retreat.

Jul 20 – 27

G$25,004 GYD per night

Guest favorite

Home in Frankfort

4.95 out of 5 average rating, 155 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.

Sep 27 – Oct 4

G$44,215 GYD per night

Guest favorite

Loft in Bangor

4.97 out of 5 average rating, 166 reviews

The Downtown Loft Bangor

Not just another AirBnB "hotel"! A historic building, the Loft has been fully renovated with a modern, minimalist vibe. Your private escape in the heart of downtown Bangor. Comfy king bed, luxury bath, chef's kitchen, and massive windows that open into a private balcony onto Main Street! We're close to everything... 0.0 miles to all things Downtown Bangor 0.5 miles to Waterfront Concerts 0.9 miles to Hollywood Slots 1.0 miles to Cross Insurance Center 1.2 miles to Eastern Maine Medical

Nov 10 – 17

G$27,653 GYD per night

Guest favorite

Home in Thorndike

4.9 out of 5 average rating, 146 reviews

Rural spacious getaway with access for adventure

Newly-renovated house in the country. Quiet getaway, hunting basecamp, or a base for excursions around mid-coast Maine. Relax in this spacious home after enjoying nearby Unity, with train station and Amish community, or Belfast with its waterfront. Take day trips to Boothbay, Camden, Rockland, Bar Harbor, or Bangor. Or just enjoy nature on the back deck and nearby forest trails. Sleeps four in two formal bedrooms, two more adults on a futon, four/six kids or young adults in a rumpus room.

Jan 4 – 11

G$21,413 GYD per night

Guest favorite

Farm stay in Winterport

4.88 out of 5 average rating, 113 reviews

Rustic cabin on organic vegetable farm

Enjoy staying in the apprentice cabin on a working organic vegetable farm. Tiny, off-grid, one-room cabin. It has a comfortable full size bed, a wood stove, cold running water in summer months, and a Coleman stove. Sit outside and enjoy our beautiful sky. Walk around the farm to see our gardens and visit with the chickens. This is a rustic farm experience. No WiFi but the sky is beautiful. There is no shower or bathing facilities. The shared outhouse (i.e. toilet) is a 1 minute walk.

Mar 9 – 16

G$16,840 GYD per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 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!

Dec 10 – 17

G$21,486 GYD per night

Guest favorite

Apartment in Belfast

4.99 out of 5 average rating, 262 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Dec 14 – 21

G$27,202 GYD per night

Guest favorite

Guest suite in Bangor

5.0 out of 5 average rating, 116 reviews

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.

Nov 14 – 21

G$24,772 GYD per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

G$17,120 GYD per night

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 193 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

Jan 16 – 23

G$20,475 GYD per night

Guest favorite

Cottage in Waltham

4.95 out of 5 average rating, 673 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

Jan 9 – 16

G$23,792 GYD per night