Holiday Homes in Portland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Portland holiday homes

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (58 reviews)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is AU$459
includes taxes & fees
25 Jan - 26 Jan
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is AU$347
includes taxes & fees
25 Jan - 26 Jan
Charming 1-bedroom ADU in wonderful Portland neighborhood

Entire ideally located home in Cape Elizabeth’s coveted seaside community

Entire ideally located home in Cape Elizabeth’s coveted seaside community
Cape Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is AU$572
includes taxes & fees
25 Jan - 26 Jan
Entire ideally located home in Cape Elizabeth’s coveted seaside community

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$543
includes taxes & fees
29 Jan - 30 Jan
Modern & Sunny House Steps from the Promenade. Private Parking!

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
8.8 out of 10, Excellent, (3 reviews)
"Great location"
United States
Mark J.
The price is AU$646
includes taxes & fees
25 Jan - 26 Jan
The 87th Townhome - Local Landmark

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AU$804
includes taxes & fees
1 Feb - 2 Feb
Willard Square Family Home

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is AU$570
includes taxes & fees
2 Feb - 3 Feb
Modern Getaway by the Sea

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is AU$978
includes taxes & fees
26 Jan - 27 Jan
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (66 reviews)
"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 AU$1,592
includes taxes & fees
22 Jan - 23 Jan
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
9.8 out of 10, Exceptional, (6 reviews)
"Great place great location. "
United States
Chris f.
The price is AU$1,236
includes taxes & fees
20 Jan - 21 Jan
Spacious 4-bedroom house located in the heart of Portland, ME.

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is AU$304
includes taxes & fees
20 Jan - 21 Jan
Escape to Positive Outlook

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14 reviews)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is AU$405
includes taxes & fees
20 Jan - 21 Jan
Fantastic Waterfront Views

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (55 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is AU$716
includes taxes & fees
23 Jan - 24 Jan
Beach House ∆ Prime Location ∆ Steps to the Ocean

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is AU$571
includes taxes & fees
20 Jan - 21 Jan
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is AU$498
includes taxes & fees
26 Jan - 27 Jan
Full sized home

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is AU$519
includes taxes & fees
25 Jan - 26 Jan
Beautiful 3BR Home with Office in Town of Brunswick with King beds

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!
Casco
10.0 out of 10, Exceptional, (14 reviews)
"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 AU$963
includes taxes & fees
20 Jan - 21 Jan
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Old Orchard Beach
9.4 out of 10, Exceptional, (14 reviews)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is AU$702
includes taxes & fees
20 Jan - 21 Jan
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Historic Kennebunkport home only 0.3 miles to Dock Square

Historic Kennebunkport home only 0.3 miles to Dock Square
Kennebunkport
10.0 out of 10, Exceptional, (81 reviews)
"Wonderful stay , pet friendly was a plus !! "
United States
Aimee S.
The price is AU$687
includes taxes & fees
27 Jan - 28 Jan
Historic Kennebunkport home only 0.3 miles to Dock Square

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
2.0 star property
Windham
The price is AU$1,031
includes taxes & fees
20 Jan - 21 Jan
Modern Lakeview Escape | 3BR/2BA
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Portland Hotel Reviews

Find out more about Portland

Portland Holiday Homes information

Number of reviews
433
Accommodation
92 Holiday Homes
Lowest Price
AU$347
Highest Price
AU$1,592

Explore a world of travel with Expedia