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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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Apartment in Searsport

4.82 out of 5 average rating, 292 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

Nov 17 – 24

€ 106 per night

Guesthouse in Bucksport

4.92 out of 5 average rating, 278 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.

Jan 1 – 8

€ 165 per night

Cottage in Glenburn

4.94 out of 5 average rating, 196 reviews

Your own private getaway on Pushaw Lake!

Welcome to Pushaw Lake! You’ll find all the comforts of home here! :-) Come for the weekend! Save 25% for a week, or 35% for a month stay! :-) Jump in the lake or go on an adventure in a kayak or canoe this summer! Bring snowmobiles, snowshoes, skis, or go ice-fishing this winter! :-) Relax... Read a book and listen to the Loons, or sit around the fire pit and say goodbye to stress! :-) You’re less than 20 minutes from Bangor International Airport, Downtown Bangor, and UMO! :-)

Feb 6 – 13

€ 164 per night

Guesthouse in Prospect

4.97 out of 5 average rating, 116 reviews

The Penobscot River Ranch Guesthouse

This unique four season property sits on 13+ acres on the Penobscot River in Prospect Maine facing Winterport. There is a 1/2 mile trail down to the river, great for hiking and snowshoeing. An awesome place to unwind with easy access for exploring mid coast and downeast Maine. Less than 10 minutes to Rt 1 and The Penobscot Narrows Bridge and Rt 1A, 18 miles to Belfast, Castine, Blue Hill, Ellsworth. About an hour to Acadia NP and 45 min to Bangor. Great views of the land, river and wildlife.

Jun 11 – 18

€ 104 per night

Guesthouse in Orrington

4.97 out of 5 average rating, 116 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 13 – 20

€ 125 per night

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.

Dec 15 – 22

€ 241 per night

Loft in Bangor

4.97 out of 5 average rating, 164 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

Oct 11 – 18

€ 151 per night

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.

Feb 9 – 16

€ 83 per night

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!

Oct 29 – Nov 5

€ 115 per night

Apartment in Belfast

4.99 out of 5 average rating, 261 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.

Feb 12 – 19

€ 143 per night

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 1 – 8

€ 91 per night

Guesthouse in Unity

5.0 out of 5 average rating, 192 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.

Oct 26 – Nov 2

€ 111 per night

Vacation rentals for every style

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Popular amenities for Winterport vacation rentals

Free parking on premises

Air conditioning

Stay near Winterport's top sights

Winterport Dragway4 locals recommend

Winterport House of Pizza6 locals recommend

Tea Maineia4 locals recommend

Winterport Winery8 locals recommend

Bantam Café3 locals recommend

Penobscot Bay Brewery3 locals recommend

Other great vacation rentals in Winterport

Home in Thorndike

4.9 out of 5 average rating, 146 reviews

Rural spacious getaway with access for adventure

Nov 26 – Dec 3

€ 107 per night

Guesthouse in Winterport

5.0 out of 5 average rating, 55 reviews

Winterport Evergreen Farm - Guest House

Apr 18 – 25

€ 176 per night

Home in Winterport

4.95 out of 5 average rating, 20 reviews

Recently renovated Hidden Gem

Sep 15 – 22

€ 251 per night

Guest suite in Hampden

4.97 out of 5 average rating, 67 reviews

In-law apartment in Hampden

Sep 9 – 16

€ 125 per night

Apartment in Hampden

5.0 out of 5 average rating, 14 reviews

Forest Retreat - Two Bedroom Apt. in Log Cabin

May 31 – Jun 7

€ 141 per night

Cottage in Hermon

4.9 out of 5 average rating, 42 reviews

Lakefront Cottage on Tracy Pond

Jan 7 – 14

€ 128 per night

Cottage in Hermon

5.0 out of 5 average rating, 21 reviews

Modern RV on Tracy Pond

Sep 22 – 29

€ 128 per night

Cottage in Hampden

4.96 out of 5 average rating, 46 reviews

Picturesque lake-front cottage close to amenities

May 11 – 18

€ 167 per night

Destinations to explore