Photo by Linda Kloss

Holiday Rentals in Winterport

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Holiday Rentals in Winterport

Waterfront cottage with deep water dock, ocean front.

10.0 out of 10, Exceptional, (86)
"Had a great time! House was very clean, had anything you could ask for. Will be back!"
Waterfront cottage with deep water dock, ocean front.

Lake Front on Beech Hill Pond, 2 Kayaks, Canoe, Paddle Board Provided

9.8 out of 10, Exceptional, (55)
"Wonderful camp, just magnificent views of the pond. The road was tough (unpaved), but it was so quiet. Again we went in October. Inside was very clean and nice, just like the photos they had on the website. We took drive to Bar Harbor very nice 👌 "
Lake Front on Beech Hill Pond, 2 Kayaks, Canoe, Paddle Board Provided

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (156)
"John and Barbara are the best hosts. I use their property every fall for when I am closing my camp. They are the best hosts ever. They give you the best greeting when you arrive and are willing to help if needed. The cabin is so sweet. I absolutely love how cozy it is. The little kitchen is perfect for cooking at the cabin. And there is enough little counter space to do a small puzzle! I am so grateful they take care of me in my camp closing."
The price is €195
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin By The Pond, Sleeps 2

Travel light long-term (safe & relaxing )special discount for travel nurse

10.0 out of 10, Exceptional, (101)
"All you could ask for. Clean, well appointed and great host!"
The price is €182
includes taxes & fees
26 Nov - 27 Nov
Travel light long-term (safe & relaxing )special discount for travel nurse

Modern, Dogs Welcome, Near Acadia National Park & Bar Harbor

10.0 out of 10, Exceptional, (149)
"Great property. Wonderful trip. "
Modern, Dogs Welcome, Near Acadia National Park & Bar Harbor

NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor

10.0 out of 10, Exceptional, (30)
"Our stay was wonderful. The surroundings were very peaceful. The cottage was smaller than we anticipated, but it was very well done and clean! Location was a little far from Acadia NP, but we didn’t mind the drive, especially because the cost of the cabins were very inexpensive. We’d stay again! Wonderful vacation!"
The price is €176
includes taxes & fees
26 Nov - 27 Nov
NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor

Overlook Cottage, Toddy Pond!

8.8 out of 10, Excellent, (43)
"We had a wonderful stay at the Overlook. The view was fantastic, use of kayaks & fire pit was great & we totally relaxed with our pup. The only thing we could have used was info on where the transfer station was, how to get the bedroom TV to work (we figured it out, though) & a starter roll of paper towels. Aside from these minute issues, this is a wonderful cabin to escape to! I’d definitely stay here again! "
Overlook Cottage, Toddy Pond!

Rustic Searsport Cabin: Loft + Sunroom on 10 Acres

9.8 out of 10, Exceptional, (72)
"The property owner was very helpful and insightful in some fun things to do around the area. The property itself was immaculate and offered a quiet and coY"
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres

Hidden Hemlock on Beech Hill Pond, Dogs Welcome

10.0 out of 10, Exceptional, (73)
"This was perfect, exactly what we were looking for. "
Hidden Hemlock on Beech Hill Pond, Dogs Welcome

Hermon Pond Studio

10.0 out of 10, Exceptional, (81)
"Excellent host! Responded to all inquiries quickly. Small studio with views of pond in back yard. Small but very comfortable, clean and quiet. "
The price is €266
includes taxes & fees
26 Nov - 27 Nov
Hermon Pond Studio

Gorgeous lakefront home w/ dock, canoe, kayaks & lake/forest views

8.8 out of 10, Excellent, (39)
"A beautiful house on the lake. We really enjoyed our time kayaking and fishing on the lake. The property is just as it was described. I would highly recommend this property if you are looking for a quiet spot to get away and relax."
Gorgeous lakefront home w/ dock, canoe, kayaks & lake/forest views

Lakefront, newly rebuilt, dog-friendly home with private beach, dock & firepit

10.0 out of 10, Exceptional, (10)
"We enjoyed the stay at your property. Beautiful location and home."
Lakefront, newly rebuilt, dog-friendly home with private beach, dock & firepit

near Acadia, Bar Harbor and Booth Bay

9.8 out of 10, Exceptional, (105)
"Very peaceful setting directly on Pushaw Lake outside of Old Town. Out of the way from the populated tourist areas but all are accessible within a 1- 2 hour drive. Communication with property manager was excellent and house had everything we needed. Old Town had good restaurant options."
near Acadia, Bar Harbor and Booth Bay

Gorgeous Oceanfront Retreat on Penobscot Bay

9.8 out of 10, Exceptional, (57)
"We enjoyed our stay with friends and family. The house was very comfortable…and that porch…that porch is just fabulous. "
The price is €2,112
includes taxes & fees
26 Nov - 27 Nov
Gorgeous Oceanfront Retreat on Penobscot Bay

Maine Wilderness Oasis: Swimming, Hiking, Fishing, Boating

10.0 out of 10, Exceptional, (33)
"- Gorgeous home - Quiet and beautiful property - Great drive to Acadia - Easy access to Bangor - WiFi and TV not reliable - We’ll be back!"
The price is €279
includes taxes & fees
2 Dec - 3 Dec
Maine Wilderness Oasis: Swimming, Hiking, Fishing, Boating

The James House on Chemo Pond Dogs Welcome

10.0 out of 10, Exceptional, (122)
"James House was perfect for our family gathering. Beautiful home, peaceful and scenic. Loved staying in this fully equipped home. Couches and beds were super comfortable. "
The James House on Chemo Pond Dogs Welcome

Secluded waterfront home with private dock, outdoor dining, firepit, WiFi & W/D

8.6 out of 10, Excellent, (11)
"Had a good nites sleep after heat was on"
Secluded waterfront home with private dock, outdoor dining, firepit, WiFi & W/D

Stunning lakefront home with 270° water views and private beach near Acadia

9.4 out of 10, Exceptional, (8)
"What an amazing location for our annual family gathering this year! The home was charming with a warm cottage atmosphere and situated right on beautiful Green Lake. It was immaculate, beautifully decorated, and offered our family the opportunity for their own space to spread out - 7 adults and 3 kids (4 and under). The setting on the lake is spectacular and we enjoyed swimming, kayaking, tubing, fishing, and relaxing by the fire pit. The property was well equipped with kitchen items, linens,...
Stunning lakefront home with 270° water views and private beach near Acadia

Oceanfront Home Overlooking Penobscot Bay , Castine Maine.<br>History abounds !

10.0 out of 10, Exceptional, (59)
"Peregrine House is situated on a quiet road in a peaceful location with a lovely view of the bay and gorgeous sunsets. There is easy access to the town of Castine and the house is a short walk to the beach where we enjoyed swimming. The house was well-equipped. The beds and living area were comfortable. Mary Lou was responsive to our questions and needs. We thoroughly enjoyed our stay."
Oceanfront Home Overlooking Penobscot Bay , Castine Maine.<br>History abounds !

MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,

10.0 out of 10, Exceptional, (25)
"Had everything we needed plus all the extra little touches. Very convenient to explore Acadia and environs."
The price is €274
includes taxes & fees
3 Dec - 4 Dec
MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Winterport you may be interested in

Country Inn at The Mall

2.0 star property
9.4 out of 10, Exceptional, (2293)
"Very clean and everyone very nice "
The price is €108
includes taxes & fees
2 Dec - 3 Dec
Country Inn at The Mall

Bangor Grande

2.5 star property
8.2 out of 10, Very good, (1330)
"Good times"
The price is €84
includes taxes & fees
8 Dec - 9 Dec
Bangor Grande

Bangor Aviator Hotel, BW Premier Collection

3.0 star property
8.6 out of 10, Excellent, (1290)
"Great service "
The price is €119
includes taxes & fees
1 Dec - 2 Dec
Bangor Aviator Hotel, BW Premier Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Winterport?

Yes, there are holiday rentals close to the most popular sights in Winterport, or you can select a more secluded option if you're looking for a relaxing stay. Winterport is known for its shopping and restaurants. Make sure you have time to check out the wineries while you're in the area.

What are some of the best holiday rentals that Winterport has to offer?

Modern, Dogs Welcome, Near Acadia National Park & Bar Harbor: This holiday home rental outside of Winterport is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winterport?

Expedia has 5 holiday rentals for your stay in Winterport.

What can I see and do in Winterport?

While exploring the area, visit family-friendly sights like Maine Discovery Museum, or get outside and enjoy nature at Penobscot River. In the wider area, you’ll find Winterport Winery and Swan Lake.

What are holiday rentals like in Winterport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterport. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.