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Portland Vacation Rentals

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Vacation Rentals in Portland

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

10.0 out of 10, Exceptional, (39)
"We had a great time!"
The price is CA $286
CA $496 total
includes taxes & fees
Sep 3 - Sep 4
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

10.0 out of 10, Exceptional, (71)
"We absolutely loved our stay and highly recommend this beautiful property. The home and amenities are exactly as described. You can’t help but have a great time. "
The price is CA $308
CA $604 total
includes taxes & fees
Aug 28 - Aug 29
Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

Waterfront Chautauqua Lake Home w/ Deck & Grill!

10.0 out of 10, Exceptional, (4)
"Beautiful sunsets, close to stores ,clean and comfy"
Waterfront Chautauqua Lake Home w/ Deck & Grill!

Bemus Point Vacation Rental

8.6 out of 10, Excellent, (107)
"We had a great time! it was everything we expected. If your looking for the Ritz go somewhere else. This cottage had everything we were hoping for.We are looking forward to next year!"
Bemus Point Vacation Rental

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

10.0 out of 10, Exceptional, (104)
"Great place for fishing and enjoying the lake"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Superb 3-bedroom, 2 bath house on lake erie. 2 min drive to Barcelona Harbor!

10.0 out of 10, Exceptional, (11)
"The house and property is in a great location! It’s close to the pier where my boys fished and kayaked. We toured the lighthouse which was so amazing. We had such a great time enjoying the local wineries as well. There was plenty of space in the house and it has everything you need. The trail to the fire pit was the best! The stars are amazing at night with the most beautiful sunsets! The host was very communicative, available, and gracious. Would definitely recommend!"
Superb 3-bedroom, 2 bath house on lake erie. 2 min drive to Barcelona Harbor!

Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining

10.0 out of 10, Exceptional, (254)
"Our stay was absolutely amazing. We love staying at the cabin. We look forward to more stays at the lake."
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining

Charming Resort in the Heart of Bemus Village on CHQ Lake

10.0 out of 10, Exceptional, (187)
"Resort on Main is such a great place to stay. You have everything you need. The house is clean and comfy. Debra and Rick are great. We plan to come back for another stay. "
Charming Resort in the Heart of Bemus Village on CHQ Lake

Modern 300 ft lakefront with pool

9.6 out of 10, Exceptional, (93)
"This house was beautiful and big and roomy and perfect for all of us cousins! The host was quick to respond to any need and went above and beyond. "
Modern 300 ft lakefront with pool

Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

9.8 out of 10, Exceptional, (104)
"Very clean, well stocked property! Close to town w/shops, restaurants,etc within walking distance. "
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

Balcony + Scenic Views: Chautauqua Lake Retreat

9.0 out of 10, Wonderful, (9)
"Everything was great. Clean and nice! "
Balcony + Scenic Views: Chautauqua Lake Retreat

Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

10.0 out of 10, Exceptional, (5)
"The house was absolutely perfect and we loved the location. It was great for our group. The kitchen was so well-appointed and the grill and fire pit made our outdoor time even more enjoyable. "
Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

Step back in time farm house

9.6 out of 10, Exceptional, (59)
"Just me for this trip but house was immaculate will handle 2 couple easily. I really enjoyed the stay"
The price is CA $86
CA $191 total
includes taxes & fees
Sep 1 - Sep 2
Step back in time farm house

Bemus Point Lake Front Cottage with Dock

9.6 out of 10, Exceptional, (82)
"Cottage and amenities were very nice. Disappointing was the several feet of muck at the lake shore which made it impossible to swim or launch a kayak from shore. The dock is unsteady and rickety; no way we could have launched a kayak from there."
Bemus Point Lake Front Cottage with Dock

Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities

2.0 out of 10, (6)
"We booked for this property a week ago and it took the money out of my account within 10 seconds. The day we went to the property I called the owner and they said it was not available. That was a long-term rental only we were only looking to rent it out for one day, but in my search, it came up and we took it and Now we are waiting for a refund. If it wasn’t available, it should’ve been in my search button in saying it. was very disappointed. We had to find last-minute hotel."
The price is CA $112
CA $166 total
includes taxes & fees
Aug 28 - Aug 29
Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities

Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake

10.0 out of 10, Exceptional, (178)
"House was great no complaints "
Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake

Private 70ft Lakefront Cabin,3br,3ba,Pet Friendly- Kayaks/Paddle boards provided

9.8 out of 10, Exceptional, (129)
"Great place loved all the extra activity items , kayaking etc"
Private 70ft Lakefront Cabin,3br,3ba,Pet Friendly- Kayaks/Paddle boards provided

3 Bedroom Cottage on the Shores of Chautauqua Lake

10.0 out of 10, Exceptional, (138)
"Comfortable house situated on shore of Lake Chautauqua with great views."
3 Bedroom Cottage on the Shores of Chautauqua Lake

Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

8.6 out of 10, Excellent, (10)
"Great location on waterfront with easy access to Stow ferry to Bemis Pt. Also only 5 miles from Chautauqua Institute. Perfect size cottage for 2 people. Very relaxing spot with friendly neighbors "
Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

Cozy Getaway ON Lake Erie

9.8 out of 10, Exceptional, (123)
"House is perfect with the best sunset views. Lots of amenities. Great communication with the host. Would definitely recommend and we look forward to coming back again!"
Cozy Getaway ON Lake Erie
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

Find out more about Portland

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland vacation rentals we have selected for you start as low as CA $86 per night. Entering your travel dates in the search wizard 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 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 Lily Dale Spiritual Center.

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.