Photo by Linda Kloss

Holiday Homes in Winterport

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winterport holiday homes

A hot tub with two chairs and a fire pit in a wooded area.

1. Timberlight Retreat | Tiny Home Cabin

Timberlight Retreat | Tiny Home Cabin
Winterport
10.0 out of 10, Exceptional, (1 review)
"This was the first time I’ve ever stayed in a Tiny home and it was adorable. An experience I am so happy to have had a chance to try. The firepit and hot tub were very relaxing."
United States
Christy L.
The price is €249
includes taxes & fees
12 Nov - 13 Nov
Timberlight Retreat | Tiny Home Cabin
A modern bathroom with a skylight, a mirror, and a towel rack.

2. Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (22 reviews)
"Property was very nice, clean and Lisa our host was very nice and helpful. Great place, highly recommend!"
United States
brian g.
The price is €192
includes taxes & fees
8 Dec - 9 Dec
Inkwell Suite at Spofford Lodge
A modern kitchen with a central island, white cabinetry, and a stainless steel range hood.

3. Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (29 reviews)
"We were greeted by deers in the property. It’s very peaceful and closest to nature."
United States
Anup B.
The price is €368
includes taxes & fees
16 Nov - 17 Nov
Tides' Reach - Private Waterfront King Beds
A living room with a fireplace, a television mounted above it, a dining area with chairs and a table, and a ceiling fan.

4. Waterfront Cape | 3BR/2 Bath| Fire Pit

Waterfront Cape | 3BR/2 Bath| Fire Pit
Brewer
9.8 out of 10, Exceptional, (6 reviews)
"The house was sparkling clean and so easy to navigate around. The view from The front of the house is spectacular."
United States
Amy
The price is €270
includes taxes & fees
12 Nov - 13 Nov
Waterfront Cape | 3BR/2 Bath| Fire Pit
A deck with wicker furniture, including a chair and a table, and a glass candle holder.

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

MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
Bangor
10.0 out of 10, Exceptional, (51 reviews)
"Enjoyed the property, close to things we wanted to do in the area."
United States
rick r.
The price is €246
includes taxes & fees
12 Nov - 13 Nov
MaineStay Central Bangor Townhouse Near airport & Acadia Park w washer & dryer,
An outdoor patio area with a table and chairs, a covered seating area, and a view of the surrounding landscape.

6. Clean & Cozy 1BR Apt#6 w/Full Kitchen & Private Bath

Clean & Cozy 1BR Apt#6 w/Full Kitchen & Private Bath
Ellsworth
8.6 out of 10, Excellent, (11 reviews)
"The property was nice, and in a good location for us to visit nearby towns"
United States
Samantha
The price is €127
includes taxes & fees
15 Nov - 16 Nov
Clean & Cozy 1BR Apt#6 w/Full Kitchen & Private Bath
A modern living room with a grey sofa, a coffee table, and a dining area with a white table and chairs.

7. New | Riverside | Fire Pit 3BR 2.5 bath

New | Riverside | Fire Pit 3BR 2.5 bath
Brewer
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful location"
United States
Ashley W.
New | Riverside | Fire Pit 3BR 2.5 bath
A wooden deck with a view of a landscaped garden and a body of water.

8. Spacious, bright, oceanfront house on the Blue Hill Peninsula.

Spacious, bright, oceanfront house on the Blue Hill Peninsula.
Penobscot
10.0 out of 10, Exceptional, (8 reviews)
"Great view and ambience!"
United States
Cameron C.
The price is €654
includes taxes & fees
1 Dec - 2 Dec
Spacious, bright, oceanfront house on the Blue Hill Peninsula.
An outdoor patio area with a table and chairs, a covered seating area, and a view of the surrounding landscape.

9. Clean&Cozy 1BR Apt5 w/Full Kitchen & Bathroom

Clean&Cozy 1BR Apt5 w/Full Kitchen & Bathroom
Ellsworth
7.6 out of 10, Good, (7 reviews)
"This was a wonderful property and we enjoyed our stay!"
United States
Logan
The price is €126
includes taxes & fees
11 Nov - 12 Nov
Clean&Cozy 1BR Apt5 w/Full Kitchen & Bathroom
A modern outdoor seating area with a fire pit, two Adirondack chairs, and a wooden deck.

10. Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater

Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater
Bangor
The price is €220
includes taxes & fees
17 Nov - 18 Nov
Field of Dreams Tiny Home w/ Jacuzzi & Personal Theater
A modern kitchen with a central island, stainless steel appliances, and wooden cabinetry.

11. Silver Oak Retreat Private Forest Getaway

Silver Oak Retreat Private Forest Getaway
Belfast
The price is €533
includes taxes & fees
11 Nov - 12 Nov
Silver Oak Retreat Private Forest Getaway
A modern kitchen with a central island, built-in appliances, and a flat-screen TV.

12. Pine Tree Retreat

Pine Tree Retreat
Hermon
The price is €427
includes taxes & fees
21 Nov - 22 Nov
Pine Tree Retreat
A kitchen with a stainless steel sink, wooden countertop, a window with a view of trees, and a hanging light fixture.

13. Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly

Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly
Old Town
9.4 out of 10, Exceptional, (13 reviews)
"It was clean, cozy, and oh so quiet ❤️"
United States
Alyssa
The price is €198
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom house. Close to everything, But quiet area. Pet Friendly
A row of colorful mobile homes with a flag displaying "WELCOME HOME" on a flagpole.

14. 5BR 3 Bath-The Maine House@Twin Hills Cottages

5BR 3 Bath-The Maine House@Twin Hills Cottages
Ellsworth
9.2 out of 10, Wonderful, (32 reviews)
"Cottage was clean and convenient location from parks"
United States
Alex
The price is €250
includes taxes & fees
11 Nov - 12 Nov
5BR 3 Bath-The Maine House@Twin Hills Cottages
A living room with a sectional sofa, a flat-screen TV, a wooden staircase, and a ceiling fan.

15. 3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay

3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay
Ellsworth
9.2 out of 10, Wonderful, (16 reviews)
"We had a wonderful, quiet, and cozy stay!"
United States
Susan J.
The price is €344
includes taxes & fees
21 Nov - 22 Nov
3-bedroom house in pleasant Ellsworth with AC, WiFi. Enjoy a cozy stay
A modern kitchen with stainless steel appliances, white cabinetry, and a dining area with wooden chairs.

16. Quiet Orono Getaway • 2 Min to I-95 & Downtown

Quiet Orono Getaway • 2 Min to I-95 & Downtown
Orono
The price is €434
includes taxes & fees
13 Nov - 14 Nov
Quiet Orono Getaway • 2 Min to I-95 & Downtown
A modern kitchen with a wooden ceiling, a dining area with a wooden table and chairs, and a view of the outdoors through large windows.

17. Meadow Place Modern 3BR Belfast Getaway with Deck

Meadow Place Modern 3BR Belfast Getaway with Deck
Belfast
The price is €577
includes taxes & fees
11 Nov - 12 Nov
Meadow Place Modern 3BR Belfast Getaway with Deck
A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

18. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is €257
includes taxes & fees
9 Dec - 10 Dec
Pretty Old House in Newport
A kitchen with white cabinets, stainless steel appliances, a window, and a potted plant.

19. Spacious 4BR| Near Airport | Covered Patio

Spacious 4BR| Near Airport | Covered Patio
Bangor dr
9.6 out of 10, Exceptional, (16 reviews)
"Quite safe clean"
United States
Danny T.
Spacious 4BR| Near Airport | Covered Patio
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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Learn more about Winterport

Along the scenic Penobscot River, this charming coastal town invites visitors to sample local vintages at Winterport Winery. Nearby adventures await at Penobscot Narrows Bridge and Observatory, where breathtaking views complement day trips to Swan Lake.

See all hotels in Winterport
A lighthouse, a house, and a coastal landscape.
Photo by Linda Kloss
Open Photo by Linda Kloss