Photo by Linda Kloss

Winterport Holiday Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winterport holiday rentals

Exterior
Hidden Forest Cabin Near Bangor & Acadia

Holiday Home in Winterport

Hidden Forest Cabin Near Bangor & Acadia
The price is HK$1,222
HK$1,747 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hidden Forest Cabin Near Bangor & Acadia
Private kitchen
The Country Farmhouse

Holiday Home in Winterport

The Country Farmhouse
The price is HK$4,294
HK$5,797 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Country Farmhouse
Fridge, microwave, oven, stovetop
Charming 3-bedroom cottage in Hampden with AC, WiFi

Cottage in Hampden

Charming 3-bedroom cottage in Hampden with AC, WiFi
2.0 star property
9.6 out of 10, Exceptional, (20)
"Great for our dogs! Wonderful hospitality! Thank you Rebekkah!"
United States
Justine
The price is HK$790
HK$1,759 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 3-bedroom cottage in Hampden with AC, WiFi
Exterior
NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor

Cottage in Hampden

NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor
10.0 out of 10, Exceptional, (45)
"Very nice place to stay."
United States
RITCH N.
The price is HK$933
HK$1,601 total
includes taxes & fees
2 Jan - 3 Jan 2026
NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor
Terrace/patio
3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay

Holiday Home in Ellsworth

3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay
10.0 out of 10, Exceptional, (2)
"Stay was excellent! Very comfortable rooms and beds! Super clean! Nice entertainment/tvs in all rooms. Very cozy. "
United States
Jason M.
The price is HK$525
HK$2,080 total
includes taxes & fees
30 Dec - 31 Dec
3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay
Living area
Cozy home in Bangor Maine

Holiday Home in Little City

Cozy home in Bangor Maine
9.6 out of 10, Exceptional, (25)
"Perfect for our large group. Had everything we needed."
United States
Madelyn F.
The price is HK$762
HK$2,161 total
includes taxes & fees
30 Dec - 31 Dec
Cozy home in Bangor Maine
Interior
Hermon Pond Studio

Apartment in Hermon

Hermon Pond Studio
10.0 out of 10, Exceptional, (94)
"The property and the view across the pond was amazing! Will be staying here again!"
United States
Louis
The price is HK$839
HK$2,016 total
includes taxes & fees
30 Dec - 31 Dec
Hermon Pond Studio
Fridge, microwave, oven, stovetop
Tides' Reach - Private Waterfront King Beds

Holiday Home in Orland

Tides' Reach - Private Waterfront King Beds
9.8 out of 10, Exceptional, (24)
"Great stay! Lots of space for everyone. Great kitchen to cook in. Loved sitting on the porch rockers every morning for coffee. Good size for a family. The two kings in one room is great if you have lots of kids. "
United States
Cass R.
The price is HK$731
HK$3,109 total
includes taxes & fees
30 Dec - 31 Dec
Tides' Reach - Private Waterfront King Beds
Fridge, microwave, oven, stovetop
Quiet single-level fully furnished house

Holiday Home in Fairmount

Quiet single-level fully furnished house
10.0 out of 10, Exceptional, (53)
"Great location, Great Host and great Accommodations!"
United States
Tess K.
The price is HK$811
HK$1,791 total
includes taxes & fees
30 Dec - 31 Dec
Quiet single-level fully furnished house
Microwave, oven, stovetop, paper towels
Cozy MaineStay Cottage #1 Hampden/Bangor

Cabin in Hampden

Cozy MaineStay Cottage #1 Hampden/Bangor
10.0 out of 10, Exceptional, (11)
"Great hostess and good location, close to hiking in Dorothea Dix Park."
United States
Loren N.
The price is HK$699
HK$1,313 total
includes taxes & fees
30 Dec - 31 Dec
Cozy MaineStay Cottage #1 Hampden/Bangor
2 bedrooms, WiFi, bed sheets
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn

Chalet in Glenburn

Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
8.0 out of 10, Very good, (1)
"Everything was perfect, If I could recommend one thing it would be free local channels on the tv"
United States
Bruce
The price is HK$1,881
HK$2,347 total
includes taxes & fees
30 Dec - 31 Dec
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
Fridge, microwave, oven, stovetop
Apartment in Bangor

Apartment in Bangor

Apartment in Bangor
9.4 out of 10, Exceptional, (3)
"Great, convenient spot. Everything was as advertised. "
United States
Rachel W.
The price is HK$1,010
HK$2,194 total
includes taxes & fees
20 Jan - 21 Jan 2026
Apartment in Bangor
Fridge, oven, stovetop, dishwasher
No bookings after 8/15/2024. Property sold. VRBO Thank you.

Cabin in Searsmont

No bookings after 8/15/2024. Property sold. VRBO Thank you.
10.0 out of 10, Exceptional, (5)
"Love the cottage and very clean and quiet."
United States
Jeanne
The price is HK$769
HK$1,093 total
includes taxes & fees
30 Dec - 31 Dec
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Exterior
Peaceful Cabin in the Woods

Cabin in Surry

Peaceful Cabin in the Woods
9.6 out of 10, Exceptional, (4)
"Wonderful stay, great cabin, exactly what we needed."
United States
Amanda G.
The price is HK$1,511
HK$3,307 total
includes taxes & fees
27 Jan - 28 Jan 2026
Peaceful Cabin in the Woods
Fridge, microwave, oven, stovetop
MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,

Holiday Home in Bangor

MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
10.0 out of 10, Exceptional, (40)
"Terrific accomodation. Highly recommend this property. "
United States
margaret f.
The price is HK$1,088
HK$2,321 total
includes taxes & fees
30 Dec - 31 Dec
MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
Dining
Charming 3-bedroom house in delightful Belfast, Maine

Holiday Home in Belfast

Charming 3-bedroom house in delightful Belfast, Maine
10.0 out of 10, Exceptional, (3)
"Fantastic spot. Well appointed and comfortable. "
United States
Ariel B.
The price is HK$1,654
HK$3,497 total
includes taxes & fees
30 Dec - 31 Dec
Charming 3-bedroom house in delightful Belfast, Maine
Interior
Bayside vista

Apartment in Bucksport

Bayside vista
10.0 out of 10, Exceptional, (15)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
The price is HK$965
HK$2,382 total
includes taxes & fees
3 Jan - 4 Jan 2026
Bayside vista
Living area
Inkwell Suite at Spofford Lodge

Holiday Home in Bucksport

Inkwell Suite at Spofford Lodge
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at Spofford Lodge. The room was beyond our expectations and immaculate. Check in process was easy and great communication by Lisa. Many thanks"
United Kingdom
Richard G.
The price is HK$1,248
HK$1,978 total
includes taxes & fees
20 Jan - 21 Jan 2026
Inkwell Suite at Spofford Lodge
Exterior
Cozy Cabin By The Pond, Sleeps 2

Cabin in Waldo

Cozy Cabin By The Pond, Sleeps 2
10.0 out of 10, Exceptional, (197)
"Just perfect accommodations "
United States
Jeffrey J.
The price is HK$933
HK$1,542 total
includes taxes & fees
30 Dec - 31 Dec
Cozy Cabin By The Pond, Sleeps 2
Exterior
Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly

Holiday Home in Old Town

Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly
9.0 out of 10, Wonderful, (8)
"Nice quiet area with good access to the area. "
United States
Peter D.
The price is HK$777
HK$1,838 total
includes taxes & fees
2 Jan - 3 Jan 2026
Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly
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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Top Winterport Hotel Reviews

Hollywood Casino Bangor

Hollywood Casino Bangor

10/10 Excellent
"The staff go above and beyond!!! In particular, Jack Reed!!!!! Also Amanda Souza!!! You are the best and we would stay there again because of your wonderful service!!!"
Phyllis 1-night trip
Posted 16 hours ago
Hollywood Casino Bangor

Find out more about Winterport

Search for holiday rentals in Winterport on Expedia! You can easily find your home rentals, villas, holiday apartments in Winterport using one of the methods below:

  • View our selection of featured holiday rentals in Winterport
  • Use the map to find apartments and other holiday homes in the Winterport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winterport while they last

Look no further and take a look at our great range of rental properties in Winterport!

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?

Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill: This highly rated holiday home rental in Winterport is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winterport?

Expedia has 6 holiday rentals for your stay in Winterport.

What can I see and do in Winterport?

While exploring the area, visit family-friendly sights like The Sports Arena, or get outside and enjoy nature at Penobscot River. In the wider area, you’ll find Winterport Winery and Penobscot Narrows Bridge and Observatory.

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.