Holiday Homes in Portland

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Our top choices for Portland holiday homes

8.4 out of 10, Very good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is NZ$521
includes taxes & fees
3 Jan - 4 Jan 2026
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
10.0 out of 10, Exceptional, (38)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$616
includes taxes & fees
4 Jan - 5 Jan 2026
Modern & Sunny House Steps from the Promenade. Private Parking!

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$766
includes taxes & fees
30 Dec - 31 Dec
Modern Getaway by the Sea

Holiday Home in Parkside

Spacious Portland Home + Parking
9.0 out of 10, Wonderful, (2)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is NZ$986
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious Portland Home + Parking
2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is NZ$684
includes taxes & fees
18 Jan - 19 Jan 2026
Chic 3-bedroom house in Munjoy Hill with off-street parking.
The price is NZ$394
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 1-bedroom ADU in wonderful Portland neighborhood

Holiday Home in West End

Huge Historic Downtown Townhome
9.8 out of 10, Exceptional, (8)
"The house is so charming and in an excellent location! It is walking distance to many options, on a quiet, beautiful street with comfortable beds and a well appointed kitchen. Easy booking and communication throughout! "
United States
Siobhain C.
The price is NZ$744
includes taxes & fees
12 Jan - 13 Jan 2026
Huge Historic Downtown Townhome

Holiday Home in West End

The 87th Townhome - Local Landmark
8.8 out of 10, Excellent, (3)
"Great location"
United States
Mark J.
The price is NZ$766
includes taxes & fees
5 Jan - 6 Jan 2026
The 87th Townhome - Local Landmark
The price is NZ$1,198
includes taxes & fees
8 Jan - 9 Jan 2026
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Holiday Home in Willard Beach

Willard Square Family Home
9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed this house! "
United States
David W.
The price is NZ$886
includes taxes & fees
11 Jan - 12 Jan 2026
Willard Square Family Home
10.0 out of 10, Exceptional, (66)
"Perfect for our girls trip! Right outside portland with gorgeous views; Meghan was so very accommodating as well!"
United States
Allysa Z.
The price is NZ$1,803
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
9.8 out of 10, Exceptional, (6)
"Great place great location. "
United States
Chris f.
The price is NZ$1,450
includes taxes & fees
30 Dec - 31 Dec
Spacious 4-bedroom house located in the heart of Portland, ME.

Holiday Home in West Point

Escape to Positive Outlook
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$325
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Holiday Home in Old Orchard Beach

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
10.0 out of 10, Exceptional, (6)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is NZ$612
includes taxes & fees
4 Jan - 5 Jan 2026
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
10.0 out of 10, Exceptional, (55)
"Excellent location for an after Labor Day vacation. Easy access to the beach. Quiet street. Very nice accommodations with plenty of room. "
United States
Charles C.
The price is NZ$836
includes taxes & fees
30 Dec - 31 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean

Holiday Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is NZ$506
includes taxes & fees
2 Jan - 3 Jan 2026
Fantastic Waterfront Views

Holiday Home in Harpswell

Camp Forever cottage
9.6 out of 10, Exceptional, (58)
"yes, nice view from backyard , fairly quiet spot , lots to do in the area , hikes , restaurants. "
United States
michael z.
The price is NZ$577
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is NZ$685
includes taxes & fees
4 Jan - 5 Jan 2026
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
10.0 out of 10, Exceptional, (14)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is NZ$1,118
includes taxes & fees
5 Jan - 6 Jan 2026
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

Holiday Home in Harpswell

Full sized home
9.8 out of 10, Exceptional, (50)
"It was a very nice house to stay at. "
United States
Anonymous traveller
The price is NZ$622
includes taxes & fees
26 Jan - 27 Jan 2026
Full sized home
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 Portland Hotel Reviews

Find out more about Portland

Portland Holiday Homes information

Number of reviews
403
Accommodation
92 Holiday Homes
Lowest Price
NZ$394
Highest Price
NZ$1,803

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