Search Holiday Homes in Portland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • 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

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The Globe House on Munjoy Hill - Walk to Breweries

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, (59 reviews)
"Nice place. Good location."
United States
Rob M.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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, (39 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
Modern & Sunny House Steps from the Promenade. Private Parking!

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.
Modern Getaway by the Sea

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
Charming 1-bedroom ADU in wonderful Portland neighborhood

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home

Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
9.0 out of 10, Wonderful, (2 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
Spacious Portland Home + Parking

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.0 out of 10, Wonderful, (4 reviews)
"Great location"
United States
Mark J.
The 87th Townhome - Local Landmark

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, (70 reviews)
"Had a really nice stay. "
United States
John F.
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"I loved spending time in this thoughtfully put together home. It is indeed chic, very personal, and our cat was comfortable here. The downstairs shower was my favorite bathroom, the shower is beautiful and cozy. The beds are wonderfully comfortable, and there were featherdown pillows in each room. My kids did argue over who got the small cute though "
United States
Penelope L.
Chic 3-bedroom house in Munjoy Hill with off-street parking.

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

7 Bed Historic Home for Group Stays

7 Bed Historic Home for Group Stays
West End
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic location , friendly and communicative hosts. Great for a group outing and would definitely stay again "
United States
Jason S.
7 Bed Historic Home for Group Stays

Historic 1849 Sea Cpt. Mansion; Weddings, Groups

Historic 1849 Sea Cpt. Mansion; Weddings, Groups
West End
10.0 out of 10, Exceptional, (2 reviews)
"Definitely recommend "
United States
Maddy Kuppens
Historic 1849 Sea Cpt. Mansion; Weddings, Groups

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
2 bedroom w/ expansive water views

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
Camp Forever cottage

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
Fantastic Waterfront Views

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
Full sized home

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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.
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

New 2-bedroom townhouse near to Town, ocean, recreational & Bowdoin College #2

New 2-bedroom townhouse near to Town, ocean, recreational & Bowdoin College #2
Brunswick
10.0 out of 10, Exceptional, (1 review)
"Properly was a cozy temporary home base while at a weekend long swim meet. The house was well-equipped in every way, and the host was very responsive and extremely accommodating. The kitchen had everything we needed and we could play games or watch movies in the downtime with a cozy fire. The close proximity to Bowdoin was also a plus. Would definitely rent again."
United States
emily p.
New 2-bedroom townhouse near to Town, ocean, recreational & Bowdoin College #2
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
450
Accommodation
82 Holiday Homes
Lowest Price
£156
Highest Price
£1,732