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$592 per night from 29 Apr to 30 Apr
AU$592
includes taxes & fees
29 Apr - 30 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
Located in Jamestown, this vacation home is on the waterfront, a 1-minute drive from Chautauqua Lake and 6 minutes from 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 8 May to 9 May
AU$634
includes taxes & fees
8 May - 9 May
With a stay at this vacation home in Chautauqua, you'll be within a 15-minute drive of Chautauqua Institution and Chautauqua Bookstore.
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, within a 15-minute drive of Chautauqua Institution and Chautauqua Lake.
Bemus Point Lake Front Cottage with Dock
Waterfront Chautauqua Lake Home w/ Stunning Views

Waterfront Chautauqua Lake Home w/ Stunning Views

Jamestown
With a stay at this vacation home in Jamestown, you'll be on the waterfront, just a 1-minute walk from Chautauqua Lake and 11 minutes by foot from Lucille Ball ...
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$486 per night from 4 May to 5 May
AU$486
includes taxes & fees
4 May - 5 May
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$758 per night from 3 May to 4 May
AU$758
includes taxes & fees
3 May - 4 May
With a stay at this vacation home in Bemus Point, you'll be within a 15-minute drive of Chautauqua Institution and Chautauqua Lake.
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
With a stay at this vacation home in Mayville, you'll be on a lake, within a 15-minute drive of Chautauqua Institution and Chautauqua Lake.
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
With a stay at this vacation home in Ashville, you'll be on the waterfront, within a 15-minute drive of Chautauqua Institution and Chautauqua Lake.
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$154
Highest Price
AU$758
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$517 per night from 27 Apr to 28 Apr
AU$517
includes taxes & fees
27 Apr - 28 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
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$238 per night from 27 Apr to 28 Apr
AU$238
includes taxes & fees
27 Apr - 28 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
Treat yourself - Enjoy spring and summer on the lake.

Treat yourself - Enjoy spring and summer on the lake.

North East
The price is AU$592 per night from 29 Apr to 30 Apr
AU$592
includes taxes & fees
29 Apr - 30 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.
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
2811 North Main Street, Jamestown, NY
Fully refundable
The price is AU$154 per night from 6 May to 7 May
AU$154
includes taxes & fees
6 May - 7 May
When you stay at Holiday Inn Express & Suites Jamestown by IHG in Jamestown, you'll be near the airport, within a 5-minute drive of Roger Tory Peterson Institute ...
Holiday Inn Express & Suites Jamestown by IHG
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.

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