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Portland Vacation Rentals

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Vacation Rentals in Portland

Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (4)
"Great property in a great location! We enjoyed our 1 night stay and would definitely return!"
The price is CA $282
CA $413 total
includes taxes & fees
Jun 16 - Jun 17
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Property grounds
Luxe Cabin /Hot Tub / EV Charger
10.0 out of 10, Exceptional, (12)
"Property was exactly as shown in the pictures. The cabins were delightful, beautiful wooden views. Lots of amenities in the main house and everything was super clean. Check-in was easy and the hosts were very communicative. Close to hiking, wineries, breweries, and Chautauqua."
Luxe Cabin /Hot Tub / EV Charger
Property grounds
Glorious, lake view. Beach access. Relax in this comfortable get-away.
10.0 out of 10, Exceptional, (7)
"Ethan hosted me for a few days during the eclipse in 2024. The house was very clean, the views are just as pictured, and the kitchen was well-stocked with tools and utensils. I would absolutely stay here again."
Glorious, lake view. Beach access. Relax in this comfortable get-away.
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Property grounds
Lake Erie Waterfront in Chautauqua Wine Region
9.8 out of 10, Exceptional, (24)
"The house and grounds are absolutely beautiful. The setting is rural and quiet, and the large deck on the back of the house is a wonderful gathering space for family and friends. The kitchen was well appointed with everything that we needed, and the decor throughout the house was pleasing."
Lake Erie Waterfront in Chautauqua Wine Region
Beach towels
Spectacular Lake Erie Sunsets with beach access
10.0 out of 10, Exceptional, (54)
"My mother and I went for a mother/daughter trip over Mother's Day weekend. We had an amazing time. We had a warm welcome message upon entering the lake house which was so sweet. We had everything we could have possibly needed right at our finger tips. Stacy is gracious enough to think of absolutely everything! The view of the lake from the front deck is lovely, and the sunsets are absolutely gorgeous. We were able to see the Northern Lights and it was amazing. Stacy is a great host and so very...
Spectacular Lake Erie Sunsets with beach access
Property grounds
Cozy Getaway ON Lake Erie
9.6 out of 10, Exceptional, (109)
"My Florida family and I stayed for my mom’s funeral. Great place for the family and friends to congregate while we were in town."
Cozy Getaway ON Lake Erie
Property grounds
Charming Lakefront Cottage Near Chautauqua Lake
9.8 out of 10, Exceptional, (9)
"It was a veey nice peaceful stay."
Charming Lakefront Cottage Near Chautauqua Lake
Property grounds
Charming Resort in the Heart of Bemus Village on CHQ Lake
10.0 out of 10, Exceptional, (148)
"Fantastic overall"
Charming Resort in the Heart of Bemus Village on CHQ Lake
On the beach
Secluded Cottage with Hidden Cove on Lake Erie
10.0 out of 10, Exceptional, (3)
"This place was simply amazing. Sunsets were the best, along with the stunning views! We'll definitely be back."
Secluded Cottage with Hidden Cove on Lake Erie
Beach
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
10.0 out of 10, Exceptional, (229)
"Thanks David and Barbara! Again, the accommodations were amazing, and the views and sunsets were beautiful as always! Can't wait to stay again! Thank you Jesse and Jenn."
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
Property grounds
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
10.0 out of 10, Exceptional, (66)
"Came down for a work trip and it was perfect for us."
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Beach
Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly
10.0 out of 10, Exceptional, (163)
"There’s so many things to love about this Lakehouse. It’s right on the water so you get to see everything from the inside if the weather is too cool to be outside. Plus, there’s plenty of yard space for corn hole and bury fire pit. There’s a gas grill on the property so we were easily able to pair meals every night plus a full kitchen. This is our go to for when we want to stay at Lake Chautauqua!"
Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly
Fridge, microwave, stovetop, dishwasher
Charming Lake Erie Getaway: Walk to Beach!
10.0 out of 10, Exceptional, (12)
"Nice quiet home. Will consider staying again in the future"
Charming Lake Erie Getaway: Walk to Beach!
Fridge, microwave, oven, stovetop
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
10.0 out of 10, Exceptional, (1)
"Excellent property, location, and host. Rachel was very friendly and responsive. Thank you!"
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Beach nearby
Bemus Point Lake Front Cottage with Dock
9.8 out of 10, Exceptional, (51)
"The property met our needs except there were no tv stations. I guess you have to know how to do streaming and apps which we do not do. We were there to visit our son and daughter in law who live outside Jamestown and it was a great location, about a 15 minute drive to their house. We had a great time."
Bemus Point Lake Front Cottage with Dock
Property grounds
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
9.6 out of 10, Exceptional, (108)
"Beautiful well kept cottage on the lake! Great location to restaurants and shops. The cottage had everything you needed!"
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Property grounds
Experience the Magic Lake Erie, Lakefront Home Astounding Views- Dog Friendly
10.0 out of 10, Exceptional, (123)
"This property had everything we were looking for. Beautiful views, quiet location, peaceful walks. The house had everything we could possibly need. The Wifi went out briefly, but Adele was immediately on the phone with Spectrum getting it sorted. Would not hesitate to stay again."
Experience the Magic Lake Erie, Lakefront Home Astounding Views- Dog Friendly
On the beach, sun loungers
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
10.0 out of 10, Exceptional, (178)
"I think I have stayed at either this cabin or the other one 4 to 5 times now. I love it here and the cabins are amazing. My girlfriends absolutely loved it and now they want to come back! I know I will definitely be back!"
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Property grounds
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
10.0 out of 10, Exceptional, (1)
"We had a wonderful visit at this tiny house on the lake. Beautiful views. The house itself was open and spacious. Ended up we had a few tag alongs and it easily accommodated 6 adults. We will be back again! PS: You can fish from the beach."
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
Beach nearby, beach towels
Private Home: Lightkeeper's Refuge steps to beach, marina and boat slip
9.8 out of 10, Exceptional, (31)
"My wife and I were looking for a comfortable/secluded home that was close to highway access. This home was perfect! We were able to easily see a lot of WNY due to the multiple nearby roads and highway. Additionally, the quaint town of Westfield was close so we were able to go grocery shopping, get coffee, and pick up take-out from multiple restaurants that were all within 5 mins. The house itself came exactly as advertised! We spent a lot of time in the back room reading, playing games, and...
Private Home: Lightkeeper's Refuge steps to beach, marina and boat slip
Don't see what you're looking for?
See all available properties in Portland
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.

Portland Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Portland cottages
Known landmarks
Lake Erie State Park, Vetter Vineyards Winery and Johnson Estate Winery
International airport
Erie, PA (ERI-Erie Intl.)

Other types of properties in Portland you may be interested in

Property grounds
Luxe Cabin /Hot Tub / EV Charger
10.0 out of 10, Exceptional, (12)
"Property was exactly as shown in the pictures. The cabins were delightful, beautiful wooden views. Lots of amenities in the main house and everything was super clean. Check-in was easy and the hosts were very communicative. Close to hiking, wineries, breweries, and Chautauqua."
Luxe Cabin /Hot Tub / EV Charger
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (4)
"Great property in a great location! We enjoyed our 1 night stay and would definitely return!"
The price is CA $282
CA $413 total
includes taxes & fees
Jun 16 - Jun 17
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Exterior
Chautauqua Harbor Hotel - Jamestown
3.5 star property
9.6 out of 10, Exceptional, (1000)
"Starbucks coffee on every floor! What else can I say? Great and friendly staff. Beds and pillows are top notch. The wife fell in love with the robes. Only place I will stay in Chataqua county. "
The price is CA $208
CA $235 total
includes taxes & fees
May 27 - May 28
Chautauqua Harbor Hotel - Jamestown
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.

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 $282 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 are some of the best vacation home rentals that Portland has to offer?

Glorious, lake view. Beach access. Relax in this comfortable get-away.: This vacation home rental outside of Portland is located on a lake and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.

Recent reviews of Portland properties
Expedia verified reviews

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

5/5 Excellent
"Starbucks coffee on every floor! What else can I say? Great and friendly staff. Beds and pillows are top notch. The wife fell in love with the robes. Only place I will stay in Chataqua county. "
A verified traveller stayed at Chautauqua Harbor Hotel - Jamestown
Posted 2 days ago
Chautauqua Harbor Hotel - Jamestown