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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Portland holiday rentals

Interior

1. 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, (61 reviews)
"The host was very accommodating and our stay was cozy, comfortable and very clean. We had a wonderful time. We would like to visit again and definitely recommend staying here! "
United States
Carrie H.
The price is HK$1,624
HK$2,863 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Coffee/tea maker, fridge, microwave, oven

2. 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, (4 reviews)
"Cute cottage. Perfect location. Very clean and the process was very smooth."
United States
Julianne C.
The price is HK$1,624
HK$2,863 total
includes taxes & fees
12 Aug - 13 Aug
Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
Property grounds

3. Small camper in the country

Small camper in the country
Dewittville
9.8 out of 10, Exceptional, (19 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$549
HK$798 total
includes taxes & fees
24 Aug - 25 Aug
Small camper in the country
Coffee/tea maker, fridge, microwave, stovetop

4. The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!

The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!
Chautauqua
The price is HK$3,099
HK$7,697 total
includes taxes & fees
13 Aug - 14 Aug
The Arlington GB: Charming Centrally Located Condo in Chautauqua Institution!
Sun-loungers

5. Lake Erie Hosta Cabin

Lake Erie Hosta Cabin
Fredonia
9.8 out of 10, Exceptional, (6 reviews)
"Perfect for my needs. Great view of the night sky, very hospitable host, and right on Lake Erie. Couldn’t get much better than that. Kick myself in the a** for not bringing my telescope."
United States
Ronald
The price is HK$1,020
HK$2,172 total
includes taxes & fees
16 Aug - 17 Aug
Lake Erie Hosta Cabin
Sun-loungers

6. Lake Erie Lily Cabin

Lake Erie Lily Cabin
Fredonia
10.0 out of 10, Exceptional, (1 review)
"Everything was great!"
United States
Matthew D.
The price is HK$1,020
HK$2,181 total
includes taxes & fees
12 Aug - 13 Aug
Lake Erie Lily Cabin
Property grounds

7. 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
21 Aug - 22 Aug
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
Coffee/tea maker, fridge, microwave, oven

8. Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
9.6 out of 10, Exceptional, (14 reviews)
"It was a very nice cute house with 2 bedrooms. It's always nice to have a half bathroom too. It was a hot weekend and AC worked well too."
United States
Chihiro
The price is HK$1,059
HK$2,128 total
includes taxes & fees
23 Aug - 24 Aug
Beautiful Wine Trail 2-BR Rental
Dining

9. Lake Erie Retreat

Lake Erie Retreat
Dunkirk
10.0 out of 10, Exceptional, (1 review)
"I was impressed with the cleanseliness and the warm and inviting atmosphere."
United States
Amanda G.
The price is HK$934
HK$1,675 total
includes taxes & fees
6 Sept - 7 Sept
Lake Erie Retreat
1 bedroom, desk, iron/ironing board, free WiFi

10. The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm
Fredonia
9.6 out of 10, Exceptional, (16 reviews)
"Superb place "
Canada
Jonathan M.
The price is HK$981
HK$1,924 total
includes taxes & fees
1 Sept - 2 Sept
The Stable at Windmill Ridge Farm
Property grounds

11. Beautiful Camper on a country road.

Beautiful Camper on a country road.
Dewittville
9.2 out of 10, Wonderful, (10 reviews)
"Nice place "
United States
Steve M.
The price is HK$698
HK$966 total
includes taxes & fees
12 Aug - 13 Aug
Beautiful Camper on a country road.
Smart TV, fireplace, DVD player, stereo

12. 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, (69 reviews)
"Home was very cozy "
United States
Richard L.
The price is HK$1,098
HK$2,420 total
includes taxes & fees
2 Sept - 3 Sept
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Smart TV, books

13. Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (30 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$1,412
HK$2,589 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Colonial in Downtown Westfield, NY
1 bedroom, desk, iron/ironing board, free WiFi

14. 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$1,483
HK$2,648 total
includes taxes & fees
8 Sept - 9 Sept
Premier St Elmo Unit w Large Balcony over Park
Coffee/tea maker, fridge, microwave, oven

15. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (93 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
9 Sept - 10 Sept
Step back in time farm house
Smart TV, DVD player, books, video library

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

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (92 reviews)
"The house was one of the cleanest I've ever stayed at. Everything was labeled clearly and the host has thought of every possible need someone staying might have/want and has it covered!I would definitely stay here again!"
United States
Michelle F.
The price is HK$2,040
HK$3,147 total
includes taxes & fees
31 Aug - 1 Sept
Walk out the door, walk onto the beach!
Smart TV, fireplace, books

17. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (22 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is HK$941
HK$2,473 total
includes taxes & fees
16 Aug - 17 Aug
The Refined Retreat
Marina

18. Cozy 2 Bedroom Canal Front Cottage With Private Dock

Cozy 2 Bedroom Canal Front Cottage With Private Dock
Ashville
9.8 out of 10, Exceptional, (54 reviews)
"It was perfect!"
United States
Justin K.
The price is HK$981
HK$2,252 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Coffee/tea maker, fridge, microwave, oven

19. Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites

Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
Ashville
10.0 out of 10, Exceptional, (2 reviews)
"This was a beautiful house!! Very clean and had everything we needed and more! The hosts were very helpful and communicated very quickly! I highly recommend staying in this house!"
United States
Janson D.
The price is HK$1,462
HK$5,036 total
includes taxes & fees
24 Aug - 25 Aug
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
Property grounds

20. Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.

Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.
North East
9.6 out of 10, Exceptional, (13 reviews)
"nice quiet place to stay,close to boat launch also"
United States
martin v.
The price is HK$981
HK$2,014 total
includes taxes & fees
1 Sept - 2 Sept
Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.
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

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

10/10 Excellent
"Nice, clean, homey. Short walk to town n dock in good shape. Grandkids enjoyed the “beach” that they have."
Kathy S. 14-night trip
Posted 3 hours ago
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

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
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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?

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!: This holiday home rental outside of Portland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 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.