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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Portland vacation rentals

Interior

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, (58 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
Jul 19 - Jul 20
Total with taxes and fees
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Fridge, microwave, oven, stovetop

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
Jul 20 - Jul 21
Total with taxes and fees
Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
Sun loungers

Lake Erie Hosta Cabin

Lake Erie Hosta Cabin
Fredonia
9.4 out of 10, Exceptional, (3 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
Jul 23 - Jul 24
Total with taxes and fees
Lake Erie Hosta Cabin
Apartment (0 Bedroom) | Interior

Historic Bemus Point Studio w/ Porch: Walk to Lake

Historic Bemus Point Studio w/ Porch: Walk to Lake
3.0 star property
Bemus Point
10.0 out of 10, Exceptional, (1 review)
"Property located in center of Bemus Point, NY. It was exactly what I was looking for at Chautauqua Lake."
United States
Mark
$434 nightly
The price is $490
Jul 31 - Aug 1
Total with taxes and fees
Historic Bemus Point Studio w/ Porch: Walk to Lake
Smart TV, fireplace, DVD player, stereo

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

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Dewittville
10.0 out of 10, Exceptional, (65 reviews)
"We enjoyed our time there."
United States
Wayne D.
$297 nightly
The price is $336
Jul 26 - Jul 27
Total with taxes and fees
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Smart TV

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Ripley
9.6 out of 10, Exceptional, (40 reviews)
"Host was very welcoming house was clean"
United States
Kevin S.
$295 nightly
The price is $333
Jul 19 - Jul 20
Total with taxes and fees
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Fridge, microwave, oven, stovetop

Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (89 reviews)
"Everything was clean and comfortable. The location was great! We enjoyed our stay."
United States
Leslie E.
$133 nightly
The price is $150
Jul 21 - Jul 22
Total with taxes and fees
Step back in time farm house
Private kitchen

3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery
Ripley
10.0 out of 10, Exceptional, (29 reviews)
"Great stay at Xinnis as usual! Everything we needed for our quick stay visiting family."
United States
Toni P.
$310 nightly
The price is $350
Jul 20 - Jul 21
Total with taxes and fees
3- Bedroom Apartment at an Award Winning Winery
Interior

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
North East
9.8 out of 10, Exceptional, (26 reviews)
"Nice place very roomy. Perfect location for the wedding we attended. "
United States
John H.
$722 nightly
The price is $810
Jul 22 - Jul 23
Total with taxes and fees
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Smart TV, fireplace

Cottage on Lake Erie

Cottage on Lake Erie
North East
10.0 out of 10, Exceptional, (67 reviews)
"We had another great stay! The location is beautiful, with views of the river and the lake from the porch. The space is very welcoming and we always enjoy cooking in the well-stocked kitchen. "
United States
Mark P.
Cottage on Lake Erie
Outdoor dining

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
Bemus Point
9.8 out of 10, Exceptional, (32 reviews)
"Bet nice house. Lots of room to spread out plus a nice bonus room upstairs. "
United States
John W.
$697 nightly
The price is $788
Jul 18 - Jul 19
Total with taxes and fees
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
Terrace/patio

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, (17 reviews)
"Very nice house and welcoming. Arrived in the area a couple hours earlier than expected and was able to check in early"
United Kingdom
Girl From N.
$420 nightly
The price is $475
Aug 8 - Aug 9
Total with taxes and fees
Lakefront w Dock-Pets OK-Amazing Views-Large Deck
Smart TV, DVD player, books, video library

Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (90 reviews)
"We had a lovely one night stay. The house was as promised- we would stay again in a heartbeat. "
United States
Wendy L.
$355 nightly
The price is $401
Aug 13 - Aug 14
Total with taxes and fees
Walk out the door, walk onto the beach!
Apartment (0 Bedroom) | Interior

Pet-friendly Loft Vacation Rental w/ Fire Pit!

Pet-friendly Loft Vacation Rental w/ Fire Pit!
3.5 star property
Bemus Point
10.0 out of 10, Exceptional, (1 review)
$321 nightly
The price is $363
Aug 5 - Aug 6
Total with taxes and fees
Pet-friendly Loft Vacation Rental w/ Fire Pit!
Property grounds

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
Jul 24 - Jul 25
Total with taxes and fees
Small camper in the country
Dining

Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10

Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10
Bemus Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful, clean family friendly home with lots of room. Well equipped kitchen, including a high chair and some board games. Very convenient to Bemus Point for shopping and restaurants. The host was very responsive. We hope to return next year!"
United States
Tara G.
$1,371 nightly
The price is $1,493
Jul 19 - Jul 20
Total with taxes and fees
Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10
Coffee/tea maker, fridge, microwave, oven

Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
10.0 out of 10, Exceptional, (11 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
$274 nightly
The price is $310
Jul 23 - Jul 24
Total with taxes and fees
Beautiful Wine Trail 2-BR Rental
Smart TV, fireplace, books

The Refined Retreat

The Refined Retreat
Celoron
9.6 out of 10, Exceptional, (19 reviews)
" wonderful place to stay "
United States
Christopher R.
$274 nightly
The price is $310
Aug 10 - Aug 11
Total with taxes and fees
The Refined Retreat
Sun loungers

Lake Erie Lily Cabin

Lake Erie Lily Cabin
Fredonia
$245 nightly
The price is $277
Jul 19 - Jul 20
Total with taxes and fees
Lake Erie Lily Cabin
Smart TV

Cozy Loft-Pet Friendly-Spacious

Cozy Loft-Pet Friendly-Spacious
Mayville
10.0 out of 10, Exceptional, (2 reviews)
"My wife and I had a wonderful stay at this beautiful Vrbo in Mayville, NY. From the moment we arrived, we felt right at home. The property was incredibly spacious, giving us plenty of room to relax and enjoy our getaway. Everything was clean, comfortable, and very welcoming.One of the things we appreciated most was how easy it was to communicate with the host. They were friendly, responsive, and made the entire process—from booking to check-out—simple and stress-free.If you're looking for a...
United States
Robert D.
$231 nightly
The price is $261
Jul 22 - Jul 23
Total with taxes and fees
Cozy Loft-Pet Friendly-Spacious
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

10/10 Excellent
"Location is great. Food very good in the restaurant. Great staff"
Jan 1-night trip
Posted 21 hours ago
Chautauqua Harbor Hotel - Jamestown

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.