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 HK$1,623
HK$2,862 total
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 HK$1,623
HK$2,862 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
A room with a foosball table, wooden flooring, and a ceiling fan.

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 HK$1,725
HK$3,944 total
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
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
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 HK$484
HK$600 total
includes taxes & fees
26 Sept - 27 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 HK$980
HK$2,003 total
includes taxes & fees
12 Oct - 13 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 HK$471
HK$842 total
includes taxes & fees
4 Oct - 5 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 HK$833
HK$1,518 total
includes taxes & fees
25 Oct - 26 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 HK$1,553
HK$2,712 total
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 HK$933
HK$1,861 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$919
HK$1,942 total
includes taxes & fees
28 Sept - 29 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 HK$1,608
HK$2,473 total
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)
"A very pleasant stay here. It was peaceful and so nice to sit on the back deck!"
United States
Mary Anne J.
The price is HK$1,035
HK$2,340 total
includes taxes & fees
4 Oct - 5 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 HK$1,304
HK$2,431 total
includes taxes & fees
27 Sept - 28 Sept
Lakefront w Dock-Pets OK-Amazing Views-Large Deck

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 HK$1,380
HK$2,517 total
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 HK$698
HK$966 total
includes taxes & fees
27 Sept - 28 Sept
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 HK$823
HK$1,786 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$572
HK$1,178 total
includes taxes & fees
28 Sept - 29 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 HK$941
HK$2,628 total
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

Athenaeum Hotel

Athenaeum Hotel

10/10 Excellent
"Staff was wonderful . We loved the concert we saw in the amphitheater. No worries about parking, traffic etc. It was awesome!"
Valerie 1-night trip
Posted 16 hours ago
Athenaeum Hotel

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

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.