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

Portland Vacation Rentals

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Check prices for these dates

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

Our top choices for Portland vacation 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.
$323 nightly
The price is $365
Aug 16 - Aug 17
Total with taxes and fees
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.
$323 nightly
The price is $365
Aug 12 - Aug 13
Total with taxes and fees
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.
$90 nightly
The price is $102
Aug 12 - Aug 13
Total with taxes and fees
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
$899 nightly
The price is $981
Aug 13 - Aug 14
Total with taxes and fees
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
$245 nightly
The price is $277
Aug 16 - Aug 17
Total with taxes and fees
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.
$246 nightly
The price is $278
Aug 12 - Aug 13
Total with taxes and fees
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
$95 nightly
The price is $107
Aug 12 - Aug 13
Total with taxes and fees
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
$240 nightly
The price is $271
Aug 23 - Aug 24
Total with taxes and fees
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.
$190 nightly
The price is $215
Sep 3 - Sep 4
Total with taxes and fees
Lake Erie Retreat
1 bedroom, desk, iron/ironing board, WiFi (free)

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.
$217 nightly
The price is $245
Sep 1 - Sep 2
Total with taxes and fees
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.
$109 nightly
The price is $123
Aug 12 - Aug 13
Total with taxes and fees
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.
$271 nightly
The price is $306
Aug 30 - Aug 31
Total with taxes and fees
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
$292 nightly
The price is $330
Aug 31 - Sep 1
Total with taxes and fees
Cozy Colonial in Downtown Westfield, NY
1 bedroom, desk, iron/ironing board, WiFi (free)

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.
$252 nightly
The price is $281
Sep 2 - Sep 3
Total with taxes and fees
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.
$133 nightly
The price is $150
Aug 14 - Aug 15
Total with taxes and fees
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.
$355 nightly
The price is $401
Aug 31 - Sep 1
Total with taxes and fees
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.
$279 nightly
The price is $315
Aug 16 - Aug 17
Total with taxes and fees
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.
$254 nightly
The price is $287
Sep 8 - Sep 9
Total with taxes and fees
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.
$608 nightly
The price is $642
Aug 16 - Aug 17
Total with taxes and fees
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.
$229 nightly
The price is $257
Sep 1 - Sep 2
Total with taxes and fees
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

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation 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 vacation.

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 vacation rental in Portland?

Yes, there are vacation rentals close to popular attractions in Portland, or you can select a more remote option if you want a relaxing place to stay.

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

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!: This vacation home rental outside of Portland is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area, you’ll find 21 Brix Winery and Lake Erie State Park.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can reserve for a couple days or more in Portland. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.