Book Holiday Homes in Portland
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Featured Holiday Homes in Portland

The Globe House on Munjoy Hill - Walk to Breweries

Rent a room in the gorgeous Holt House

Elegant condo - walk to Portland's best restaurants & Old Port

Prime City Living Townhouse by RedAwning

Convenient Portland home 3 miles from Downtown

Huge Historic Downtown Townhome

Luxurious Penthouse with Modern Design in Downtown

Coastal Retreat: Hot Tub, Firepit, Luxury Stay

Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade
Portland Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Portland vacation homes are the perfect way for you to wing it.
Holiday houses in Portland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Portland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Portland adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Portland with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Portland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Portland Holiday Homes essential information
Accommodation | 89 Holiday Homes |
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Lowest Price | AU$146 |
Highest Price | AU$1,063 |
Popular accommodation | The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Elegant condo - walk to Portland's best restaurants & Old Port, Prime City Living Townhouse by RedAwning, Convenient Portland home 3 miles from Downtown, Huge Historic Downtown Townhome, Luxurious Penthouse with Modern Design in Downtown, Coastal Retreat: Hot Tub, Firepit, Luxury Stay, Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade |
Top trending hotels in Portland

The Westin Portland Harborview

Portland Harbor Hotel

Clarion Hotel Portland

Cambria Hotel Portland Downtown-Old Port
More ways to explore Portland
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^Subject to availability and chosen travel dates.