Photo by Matthew Jay
Search Vacation Homes in Portland
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Compare 154 Vacation Homes in Portland with updated reviews, rates, and availability.
Beachfront Retreat in Wine Country w/ Sunset View!
Beachfront Retreat in Wine Country w/ Sunset View!
10.0 out of 10, Exceptional, (5)
The price is AED 1,561
AED 3,135 total
includes taxes & fees
25 Nov - 26 Nov
Step back in time farm house
Step back in time farm house
9.8 out of 10, Exceptional, (43)
The price is AED 253
AED 526 total
includes taxes & fees
3 Dec - 4 Dec
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard
9.6 out of 10, Exceptional, (80)
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!
9.8 out of 10, Exceptional, (100)
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
10.0 out of 10, Exceptional, (44)
The price is AED 477
AED 901 total
includes taxes & fees
23 Nov - 24 Nov
"The Grape Escape"-Stylish Retreat Wine Country PA
"The Grape Escape"-Stylish Retreat Wine Country PA
9.8 out of 10, Exceptional, (11)
Quaint Lake Erie Vacation Cottage
Quaint Lake Erie Vacation Cottage
9.4 out of 10, Exceptional, (21)
Walk out the door, walk onto the beach!
Walk out the door, walk onto the beach!
10.0 out of 10, Exceptional, (63)
The price is AED 731
AED 1,579 total
includes taxes & fees
3 Dec - 4 Dec
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types 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
10.0 out of 10, Exceptional, (21)
The price is AED 657
AED 992 total
includes taxes & fees
24 Nov - 25 Nov
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
10.0 out of 10, Exceptional, (35)
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
10.0 out of 10, Exceptional, (86)
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.
Recent reviews of Portland hotels
Recent reviews of Portland hotels
5/5 Excellent
"Second time staying here. A fabulous little gem. It’s the overall vibe including the people that work there. Thanks Sam at Front Desk & Sophia in the dining room. First time eating there - unbelievably delicious.
The morning view from our room was fabulous.
Thanks Chautauqua Harbor Hotel for another lovely stay :). "
A verified traveler stayed at Chautauqua Harbor Hotel - Jamestown
Posted 15 hours ago