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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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Home in Stetson

4.96 out of 5 average rating, 174 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

Guest suite in Orrington

4.97 out of 5 average rating, 105 reviews

Lake front luxury retreat with an Island View

Indulge in lakeside luxury at our modern, waterfront studio retreat! Perched on the water's edge, this pet-friendly haven offers: Private dock and lake access · Spa-inspired indoor and outdoor showers · Cozy fire pit for a relaxing movie night under the stars · Unbeatable views and direct access to the lake for swimming & soaking up the sun · The serene sounds of loons and unforgettable memories to cherish. A short drive from town, experience the best of Maine living in style and tranquility.

Cabin in Eastbrook

4.96 out of 5 average rating, 241 reviews

Hemlock Cabin.

Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Guesthouse in Prospect

4.97 out of 5 average rating, 124 reviews

The Penobscot River Ranch Guesthouse

This unique four season property sits across from conservation land on the Penobscot River in Prospect Maine. 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.

Home in Bangor

4.8 out of 5 average rating, 357 reviews

Cozy House Surrounded by Nature in Bangor

Connected farmhouse with a modern kitchen, spacious lounge, 3 queen beds, and fireplace. Conveniently located just 5 minutes away from the Bangor airport, and 10 minutes from downtown. Enjoy a 55" TV with streaming, WiFi, a hot bath, a very comfy bed, wood fire, full kitchen, and nature trail. We have common courtesy house rules and simple self-checkin. There's no cleaning required on checkout. Includes complimentary coffee, snacks, toiletries, and parking for two cars. See you soon!

Cottage in Trenton

4.97 out of 5 average rating, 331 reviews

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

Guesthouse in Orland

4.99 out of 5 average rating, 137 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!

Yurt in Appleton

4.96 out of 5 average rating, 216 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Guest suite in Mount Desert

4.97 out of 5 average rating, 215 reviews

Otter Creek Retreat hosted by Elaine & Richard

Between Bar Harbor and Seal Harbor, 10 minutes by car to both and just 5 minutes by car to the Otter Cliff entrance to Acadia Park Loop Road. Walk to the Causeway via the Grover Path in 15 minutes. 5-minute walk to the Cadillac South Ridge Trail. Large high-ceiling studio with private parking and entrance with beautiful sheltered second-story deck. We are on the Blackwoods/Bar Harbor bus route so you can catch the free Island Explorer LL Bean buses to Bar Harbor and back.

Guest suite in Orono

4.99 out of 5 average rating, 495 reviews

Private Studio in the Heart of Orono

Slip into the comforts of a private, clean, and modern suite. A plush mattress, crisp white linens, granite countertops, and a rain shower. Walking distance to many of Orono's microbreweries and restaurants. Four minutes to UMaine campus (1 mile), 10 minutes to Bangor, 1 hour and 20 minutes to Acadia National Park/Bar Harbor. *The building next door is undergoing renovations. Guests may hear some light construction noise Mon-Fri during normal working hours.*

Cottage in Waltham

4.95 out of 5 average rating, 745 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

Cottage in Hampden

4.99 out of 5 average rating, 274 reviews

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!

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 Winery8 locals recommend

Winterport House of Pizza6 locals recommend

Winterport Dragway4 locals recommend

Tea Maineia4 locals recommend

Penobscot Bay Brewery3 locals recommend

Bantam Café3 locals recommend

Other great vacation rentals in Winterport

Home in Belfast

5 out of 5 average rating, 36 reviews

Sail Loft

Guesthouse in Orland

5 out of 5 average rating, 60 reviews

Studio on Orland River

Home in Verona Island

4.96 out of 5 average rating, 81 reviews

Vernon's View

Tiny home in Monroe

5 out of 5 average rating, 17 reviews

The Cabin at Lawson Woods

Tiny home in Bangor

4.84 out of 5 average rating, 25 reviews

Field of Dreams Tiny Home

Cabin in Searsmont

4.98 out of 5 average rating, 66 reviews

Birch Hill Cabin w/Hot Tub

Home in Brooks

4.98 out of 5 average rating, 59 reviews

Cozy New Home with Hot Tub: Cornerton

Home in Winterport

5 out of 5 average rating, 9 reviews

Winterport Village House A/C, Gas Fire Pit, WiFi

Quick stats about vacation rentals in Winterport

Total rentals
40 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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 $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 free parking, over 10 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 10 vacation rentals for guests traveling with pets.
Do house rentals in Winterport have wifi?
Absolutely! We offer over 10 house rentals with wifi in Winterport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winterport?
Winterport has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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