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

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
With a stay at this vacation home in South Portland (Willard), you'll be within a 15-minute drive of Maine Mall and Casco Bay.
Charming 110-year former Inn 10' from the Ocean!
Save an average of 15% on thousands of hotels when you're signed in
NEW LISTING! Prime City Living Townhouse by RedAwning

NEW LISTING! Prime City Living Townhouse by RedAwning

2 out of 5
Portland
Fully refundable
The price is AU$914 per night from 6 Jan to 7 Jan
AU$914
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at this vacation home in Portland (Parkside), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
NEW LISTING! Prime City Living Townhouse by RedAwning
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 within a 10-minute drive of Maine Mall and Casco Bay.
Rent a room in the gorgeous Holt House
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade

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

Portland
With a stay at this vacation home in Portland (East End), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
The best place for the money!!!

The best place for the money!!!

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
The best place for the money!!!
Modern & Sunny House Steps from the Promenade. Private Parking!

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

Portland
The price is AU$596 per night from 6 Jan to 7 Jan
AU$596
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Modern & Sunny House Steps from the Promenade. Private Parking!
Beautiful, single story ranch. Next to city park with ocean view!

Beautiful, single story ranch. Next to city park with ocean view!

Portland
The price is AU$1,813 per night from 22 Jan to 23 Jan
AU$1,813
includes taxes & fees
22 Jan - 23 Jan 2025
With a stay at this vacation home in Portland (Back Cove), you'll be within a 15-minute drive of Maine Mall and Casco Bay.
Beautiful, single story ranch. Next to city park with ocean view!
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
70 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$1,813
Popular accommodation
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Charming 110-year former Inn 10' from the Ocean!, NEW LISTING! Prime City Living Townhouse by RedAwning, Rent a room in the gorgeous Holt House, Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade, The best place for the money!!!, Modern & Sunny House Steps from the Promenade. Private Parking!, Beautiful, single story ranch. Next to city park with ocean view!

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$176 per night from 7 Jan to 8 Jan
AU$176
includes taxes & fees
7 Jan - 8 Jan 2025
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
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 25 Dec to 26 Dec
AU$166
includes taxes & fees
25 Dec - 26 Dec
With a stay at Ramada Plaza by Wyndham Portland in Portland (Nasons Corner), you'll be within a 10-minute drive of Maine Mall and Happy Wheels Skate Center.
Ramada Plaza by Wyndham Portland
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$258 per night from 25 Dec to 26 Dec
AU$258
includes taxes & fees
25 Dec - 26 Dec
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Portland Harbor Hotel
Save an average of 15% on thousands of hotels when you're signed in
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 5 Jan to 6 Jan
AU$254
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Canopy by Hilton Portland Waterfront
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.