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

Our top choices for Portland vacation 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.
$305 nightly
The price is $345
Sep 28 - Sep 29
Total with taxes and fees
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.
$305 nightly
The price is $345
Oct 4 - Oct 5
Total with taxes and fees
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
$420 nightly
The price is $475
Oct 19 - Oct 20
Total with taxes and fees
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.
$85 nightly
The price is $96
Sep 28 - Sep 29
Total with taxes and fees
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, (17 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
$222 nightly
The price is $251
Oct 6 - Oct 7
Total with taxes and fees
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
$95 nightly
The price is $107
Oct 6 - Oct 7
Total with taxes and fees
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.
$176 nightly
The price is $199
Oct 21 - Oct 22
Total with taxes and fees
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
$295 nightly
The price is $333
Sep 28 - Sep 29
Total with taxes and fees
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.
$191 nightly
The price is $216
Sep 29 - Sep 30
Total with taxes and fees
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.
$212 nightly
The price is $240
Sep 28 - Sep 29
Total with taxes and fees
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, (96 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
$276 nightly
The price is $312
Oct 6 - Oct 7
Total with taxes and fees
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.
$252 nightly
The price is $285
Oct 4 - Oct 5
Total with taxes and fees
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.
$229 nightly
The price is $259
Sep 28 - Sep 29
Total with taxes and fees
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
$281 nightly
The price is $318
Sep 28 - Sep 29
Total with taxes and fees
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.
$109 nightly
The price is $123
Sep 28 - Sep 29
Total with taxes and fees
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.
$195 nightly
The price is $217
Sep 28 - Sep 29
Total with taxes and fees
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, (100 reviews)
"Everything was clean and comfortable. The location was great! We enjoyed our stay."
United States
Leslie E.
$133 nightly
The price is $150
Sep 28 - Sep 29
Total with taxes and fees
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.
$287 nightly
The price is $317
Sep 28 - Sep 29
Total with taxes and fees
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 2 days ago
Athenaeum Hotel

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?

Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake: This vacation home rental outside of Portland is located on a lake and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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.