Book Holiday Homes in Portland

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Featured Holiday Homes in Portland

Treat yourself - Enjoy spring and summer on the lake.

Treat yourself - Enjoy spring and summer on the lake.

North East
The price is AU$600 per night from 9 Apr to 10 Apr
AU$600
includes taxes & fees
9 Apr - 10 Apr
When you stay at this vacation home in North East, you'll be on a lake, just steps from Lake Erie and a 2-minute drive from Mazza Vineyards.
Treat yourself - Enjoy spring and summer on the lake.
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

Jamestown
With a stay at this vacation home in Jamestown, you'll be on the waterfront, within a 10-minute drive of Chautauqua Lake and Lucille Ball Desi Arnaz Museum.
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard
Stunning Vacation retreat. Heated pool, ideal for family vacations or friends.

Stunning Vacation retreat. Heated pool, ideal for family vacations or friends.

Mayville
The price is AU$634 per night from 7 Apr to 8 Apr
AU$634
includes taxes & fees
7 Apr - 8 Apr
With a stay at this vacation home in Chautauqua, you'll be within a 15-minute drive of Chautauqua Lake and Chautauqua Institution.
Stunning Vacation retreat. Heated pool, ideal for family vacations or friends.
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Bemus Point Lake Front Cottage with Dock

Bemus Point Lake Front Cottage with Dock

Bemus Point
With a stay at this vacation home, you'll be centrally located in Bemus Point, a 1-minute drive from Chautauqua Lake and 11 minutes from Chautauqua ...
Bemus Point Lake Front Cottage with Dock
Waterfront Chautauqua Lake Home w/ Stunning Views

Waterfront Chautauqua Lake Home w/ Stunning Views

Jamestown
When you stay at this vacation home in Jamestown, you'll be on the waterfront, just steps from Chautauqua Lake and 11 minutes by foot from Lucille Ball Memorial ...
Waterfront Chautauqua Lake Home w/ Stunning Views
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Dewittville
The price is AU$487 per night from 6 Apr to 7 Apr
AU$487
includes taxes & fees
6 Apr - 7 Apr
Located in Dewittville, this vacation home is in a rural location, a 5-minute drive from Chautauqua Lake and 6 minutes from Dewittville Bay.
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Bemus Point
The price is AU$784 per night from 11 Apr to 12 Apr
AU$784
includes taxes & fees
11 Apr - 12 Apr
Located in Bemus Point, this vacation home is within a 15-minute drive of Chautauqua Lake and Chautauqua Institution.
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
Chautauqua Lake House with large deck- 4 bedroom & 4 bathrooms

Chautauqua Lake House with large deck- 4 bedroom & 4 bathrooms

Mayville
When you stay at this vacation home in Mayville, you'll be on a lake, within a 15-minute drive of Chautauqua Lake and Chautauqua Institution.
Chautauqua Lake House with large deck- 4 bedroom & 4 bathrooms
Create your family memories at our nautical lakeside home!

Create your family memories at our nautical lakeside home!

Ashville
When you stay at this vacation home in Ashville, you'll be on the waterfront, within a 15-minute drive of Chautauqua Lake and Chautauqua Institution.
Create your family memories at our nautical lakeside home!
Don't see what you're looking for?
See all available properties in Portland
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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
183 Holiday Homes
Lowest Price
AU$209
Highest Price
AU$784
Popular accommodation
Treat yourself - Enjoy spring and summer on the lake., Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard, Stunning Vacation retreat. Heated pool, ideal for family vacations or friends., Bemus Point Lake Front Cottage with Dock, Waterfront Chautauqua Lake Home w/ Stunning Views, Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away. , Quaint historic home in the heart of Bemus Point Village- a stroll to the water!, Chautauqua Lake House with large deck- 4 bedroom & 4 bathrooms, Create your family memories at our nautical lakeside home!

Top trending hotels in Portland

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Portland
The price is AU$482 per night from 6 Apr to 7 Apr
AU$482
includes taxes & fees
6 Apr - 7 Apr
With a stay at this cabin in Portland, you'll be a 1-minute drive from Lake Erie and 5 minutes from Lake Erie State Park.
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Clarion Hotel Conference Center on Lake Erie

Clarion Hotel Conference Center on Lake Erie

2.5 out of 5
30 Lake Shore Dr E, Dunkirk, NY
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 1 May to 2 May
AU$209
includes taxes & fees
1 May - 2 May
Located in Dunkirk, Clarion Hotel Conference Center on Lake Erie is connected to the convention center, within a 5-minute drive of Dunkirk Lighthouse and Veterans ...
Clarion Hotel Conference Center on Lake Erie
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave, Celoron, NY
Fully refundableReserve now, pay when you stay
The price is AU$242 per night from 6 Apr to 7 Apr
AU$242
includes taxes & fees
6 Apr - 7 Apr
Located in Celoron, Chautauqua Harbor Hotel - Jamestown is a 1-minute drive from Chautauqua Lake and 7 minutes from Lucille Ball Desi Arnaz Museum.
Chautauqua Harbor Hotel - Jamestown
Save an average of 15% on thousands of hotels when you're signed in
Treat yourself - Enjoy spring and summer on the lake.

Treat yourself - Enjoy spring and summer on the lake.

North East
The price is AU$600 per night from 9 Apr to 10 Apr
AU$600
includes taxes & fees
9 Apr - 10 Apr
When you stay at this vacation home in North East, you'll be on a lake, just steps from Lake Erie and a 2-minute drive from Mazza Vineyards.
Treat yourself - Enjoy spring and summer on the lake.
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.