A large suspension bridge with a distinctive gothic arch design, spanning over a forested area.

Portland Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Portland holiday rentals

A modern kitchen with dark cabinetry, a central island, and a dining area with a chair and table.

1. Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly

Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
Portland
9.6 out of 10, Exceptional, (7 reviews)
"Cute cottage. Perfect location. Very clean and the process was very smooth."
United States
Julianne C.
The price is AU$502
includes taxes & fees
27 Sept - 28 Sept
Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
A spiral staircase with wooden steps and metal railings, leading to an upper level with a skylight.

2. Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Portland
10.0 out of 10, Exceptional, (63 reviews)
"Peaceful, great location and beautiful interior/decor. Wished we could have stayed longer. Nice proximity to local vineyards and local towns. Our pups also appreciated standing on the overlook and peering out to ever changing Lake Erie."
United States
amy k.
The price is AU$491
includes taxes & fees
5 Oct - 6 Oct
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
A wooden room with a bed, pillows, a hanging plant, and a window with a view of greenery.

3. Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub

Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub
Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting near Lake Erie and hiking trails. Fun design, great for families/small groups. Bring your own drinking water though if you mind sulfer."
United States
Laura
The price is AU$682
includes taxes & fees
19 Oct - 20 Oct
Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub
A beach setting with a chair and a table, both covered with a white cloth.

4. Lake Erie Hosta Cabin

Lake Erie Hosta Cabin
Fredonia
10.0 out of 10, Exceptional, (11 reviews)
"Very peaceful and private property with stunning views of the Lake Erie.Cabin had all we needed except may be pack up some fans as it gets hot sometimes. Host is wonderful accommodated my extra adults kids who decided to come at the last minute.Extra futon and pillows were provided.Electirc plate helped making breakfast Omelette and stove top for tea.We enjoyed our stay very much."
United States
Malika
The price is AU$386
includes taxes & fees
7 Oct - 8 Oct
Lake Erie Hosta Cabin
A beach with a chair and a table, both covered with a white cloth.

5. Lake Erie Lily Cabin

Lake Erie Lily Cabin
Fredonia
10.0 out of 10, Exceptional, (2 reviews)
"Property incredible! Next year will plan to spend more time at the property for some down time. Many classes but forgot to rest in-between. Property owner is very gracious and open to discussing whatever😄. Will try again next year"
United States
Lisa E
The price is AU$386
includes taxes & fees
7 Oct - 8 Oct
Lake Erie Lily Cabin
A white RV parked in a wooded area with a paved path leading to it.

6. Small camper in the country

Small camper in the country
Dewittville
9.8 out of 10, Exceptional, (21 reviews)
"Had a great time, unfortunately it rained the entire time we were there but the Rv was very clean and the host was amazing. We will definitely come visit again."
United States
Ashley M.
The price is AU$134
includes taxes & fees
25 Sept - 26 Sept
Small camper in the country
A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

7. Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
9.8 out of 10, Exceptional, (16 reviews)
"You have the whole house so it is nice and quiet. I stayed here twice this summer and it was very convenient and relaxing. AC works well and the bed is comfortable."
United States
Chihiro
The price is AU$357
includes taxes & fees
4 Oct - 5 Oct
Beautiful Wine Trail 2-BR Rental
A forested area with a fire pit surrounded by green plastic chairs.

8. Comfortable Camper a few miles off thruway and area attractions. Fire ring wood

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
Forestville
9.0 out of 10, Wonderful, (2 reviews)
"Very clean and peaceful. The host was very responsive to any communication. Would definitely stay here again."
United States
Kathleen
The price is AU$154
includes taxes & fees
1 Oct - 2 Oct
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
A modern living room with a dining table, sofa, and staircase.

9. Lake Erie Retreat

Lake Erie Retreat
Dunkirk
10.0 out of 10, Exceptional, (3 reviews)
"Excellent communication with the host. Great location and very clean!"
United States
Christina F.
The price is AU$289
includes taxes & fees
21 Oct - 22 Oct
Lake Erie Retreat
A modern kitchen with wooden chairs, a dining table, and a black cabinet.

10. Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (31 reviews)
"Great clean place in a good part of town so we were able to walk to the bars and restaurants in a few minutes. Will for sure book this same place next year when we are up on fishing trip and wine arounds."
United States
Ken
The price is AU$486
includes taxes & fees
27 Sept - 28 Sept
Cozy Colonial in Downtown Westfield, NY

11. The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm
Fredonia
9.6 out of 10, Exceptional, (18 reviews)
"Superb place "
Canada
Jonathan M.
The price is AU$342
includes taxes & fees
7 Oct - 8 Oct
The Stable at Windmill Ridge Farm
A modern living room with a brick accent wall, a sofa, a bed, and a dining area.

12. Cozy Loft-Pet Friendly-Spacious

Cozy Loft-Pet Friendly-Spacious
Mayville
10.0 out of 10, Exceptional, (4 reviews)
"Great stay. Clean loft and pet friendly.Host was easy to"
United States
Angela W.
The price is AU$358
includes taxes & fees
27 Sept - 28 Sept
Cozy Loft-Pet Friendly-Spacious
A living room with a stone fireplace, a television, and a dining area in the background.

13. Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (95 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
The price is AU$443
includes taxes & fees
6 Oct - 7 Oct
Walk out the door, walk onto the beach!
A spacious living area with a dining table, a sofa, and a kitchen with wooden cabinets and a built-in island.

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

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Dewittville
9.8 out of 10, Exceptional, (72 reviews)
"We had a great time. Was the perfect home away from home for a couple days."
United States
Juliann G.
The price is AU$419
includes taxes & fees
7 Oct - 8 Oct
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
A two-story house with a deck, a barbecue grill, and a sofa.

15. Lakefront w Dock-Pets OK-Amazing Views-Large Deck

Lakefront w Dock-Pets OK-Amazing Views-Large Deck
Chautauqua Lake
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful views of the lake and a nice little place to stay!"
United States
Kierstyn I.
The price is AU$409
includes taxes & fees
28 Sept - 29 Sept
Lakefront w Dock-Pets OK-Amazing Views-Large Deck
A small, single-story mobile home with a front door, a window, and a barbecue grill in the yard.

16. Spacious 3BR Home with Pool Table & Patio Near Lake Erie

Spacious 3BR Home with Pool Table & Patio Near Lake Erie
Westfield
The price is AU$449
includes taxes & fees
28 Sept - 29 Sept
Spacious 3BR Home with Pool Table & Patio Near Lake Erie
A grassy pathway leading to a white RV with a visible logo.

17. Beautiful Camper on a country road.

Beautiful Camper on a country road.
Dewittville
9.2 out of 10, Wonderful, (15 reviews)
"Nice place "
United States
Steve M.
The price is AU$176
includes taxes & fees
1 Oct - 2 Oct
Beautiful Camper on a country road.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

18. Premier St Elmo Unit w Large Balcony over Park

Premier St Elmo Unit w Large Balcony over Park
Chautauqua
10.0 out of 10, Exceptional, (1 review)
"This unit was perfect and just as described in the listing. The owners were very good with communication and helping us be prepared for our trip."
United States
Kristy C.
The price is AU$395
includes taxes & fees
22 Oct - 23 Oct
Premier St Elmo Unit w Large Balcony over Park
A kitchen with white cabinets, a granite countertop, and a ceiling light fixture.

19. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (99 reviews)
"Everything was clean and comfortable. The location was great! We enjoyed our stay."
United States
Leslie E.
The price is AU$214
includes taxes & fees
25 Sept - 26 Sept
Step back in time farm house
A campfire with four Adirondack chairs around it, set in a forested area with a picnic table in the background.

20. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful view of the lake. Very nice little house and quiet. "
United States
Joelyn G.
The price is AU$467
includes taxes & fees
27 Sept - 28 Sept
Quiet Escape, Peaceful Lake Glimpses
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.
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Top Portland Hotel Reviews

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

8/10 Good
"The property is lovely. Derek the bartender is their best employee, and he is fantastic. They promised coffee on every floor in the morning starting at 6am. On neither day was their coffee on our floor. When we questioned it in the lobby, we were told it should have been there. Well, they didn't even have it in the lobby until 8:30. No one even offered to look into it. When we mentioned it at checkout, the front desk person simply said, "I'm sorry." Also, the kitchen was dreadfully slow. These may sound like little things, but when the hotel is charging top dollar, it should deliver on what it advertises and should be more eager to please. Their hotel in Clayton, NY is managed way more efficiently."
Mary 2-night trip
Posted 17 hours ago
Chautauqua Harbor Hotel - Jamestown

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as AU$214 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portland has to offer?

Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake: This holiday home rental outside of Portland is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Portland?

While exploring the area, visit family-friendly sights like Chautauqua Belle Steamboat, or get outside and enjoy nature at Lake Erie. In the wider area, you’ll find 21 Brix Winery and Lake Erie State Park.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip.