Book Holiday Homes in Portland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Portland

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Rent a room in the gorgeous Holt House
Elegant condo - walk to Portland's best restaurants & Old Port

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

Portland
The price is AU$667 per night from 29 Apr to 30 Apr
AU$667
includes taxes & fees
29 Apr - 30 Apr
With a stay at this vacation home, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Elegant condo - walk to Portland's best restaurants & Old Port
Save an average of 15% on thousands of hotels when you're signed in
Prime City Living Townhouse by RedAwning

Prime City Living Townhouse by RedAwning

2 out of 5
75 Carleton St, Portland, ME
The price is AU$856 per night from 29 Apr to 30 Apr
AU$856
includes taxes & fees
29 Apr - 30 Apr
With a stay at this vacation home in Portland (Parkside), you'll be a 4-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Prime City Living Townhouse by RedAwning
Convenient Portland home 3 miles from Downtown

Convenient Portland home 3 miles from Downtown

Portland
The price is AU$1,063 per night from 1 May to 2 May
AU$1,063
includes taxes & fees
1 May - 2 May
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Convenient Portland home 3 miles from Downtown
Huge Historic Downtown Townhome

Huge Historic Downtown Townhome

Portland
The price is AU$663 per night from 29 Apr to 30 Apr
AU$663
includes taxes & fees
29 Apr - 30 Apr
With a stay at this vacation home, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Huge Historic Downtown Townhome
Luxurious Penthouse with Modern Design in Downtown

Luxurious Penthouse with Modern Design in Downtown

Portland
Located in Portland (Downtown Portland), this vacation home is within a 10-minute drive of Thompson's Point and Maine Mall.
Luxurious Penthouse with Modern Design in Downtown
Coastal Retreat: Hot Tub, Firepit, Luxury Stay

Coastal Retreat: Hot Tub, Firepit, Luxury Stay

Portland
The price is AU$938 per night from 1 May to 2 May
AU$938
includes taxes & fees
1 May - 2 May
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Coastal Retreat: Hot Tub, Firepit, Luxury Stay
Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade

Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade

Portland
Located in Portland (Munjoy Hill), this vacation home is within a 10-minute drive of Thompson's Point and Maine Mall.
Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade
Don't see what you're looking for?
See all available properties in Portland
View all properties
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.

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
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

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 26 May to 27 May
AU$237
includes taxes & fees
26 May - 27 May
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$352 per night from 4 May to 5 May
AU$352
includes taxes & fees
4 May - 5 May
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 1 May to 2 May
AU$146
includes taxes & fees
1 May - 2 May
With a stay at Clarion Hotel Portland in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Clarion Hotel Portland
Save an average of 15% on thousands of hotels when you're signed in
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$300 per night from 30 Apr to 1 May
AU$300
includes taxes & fees
30 Apr - 1 May
Located in Portland (East Bayside), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Cambria Hotel Portland Downtown-Old Port
Don't see what you're looking for?
See all available properties in Portland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.