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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
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, 7 reviews
"great place to stay, unwind and relax. will go back for sure! very clean and well stocked, great location to wineries and restaurants."
The price is $207
$303 total
includes taxes & fees
Jul 8 - Jul 9
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
Beach | On the beach, sun loungers
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
10.0 out of 10, Exceptional, 231 reviews
"We absolutely love it here, & what a delightful surprise to find that Dave had remodeled & upgraded the one bed/one bath to two bed/two bath! It is just a gorgeous space, perfect for us. We love the fire pit in the morning, to make a fire & have our coffee & tea out there by the lake. The whole experience is so good, we've already made our reservations for next year. It's one of the highlights of our year!"
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
Lake Erie Waterfront in Chautauqua Wine Region
Property grounds
Lake Erie Waterfront in Chautauqua Wine Region
9.8 out of 10, Exceptional, 24 reviews
"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
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Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Property grounds
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
10.0 out of 10, Exceptional, 69 reviews
"The house was perfect for our family. We had 3 adults fro Florida, 2 adults from Iowa, and 3 adults Ana a 7 year old grandson. The 4 bedrooms were laid out perfectly for us. The whole house was great and a dining table to sit 8+ for a meal. Kitchen was very equipped and met all our needs. The patio was also very nice. The only negative was the fishing was not good for the days we were here. This was our third trip here and hope to return next year."
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Glorious, lake view. Beach access. Relax in this comfortable get-away.
Property grounds
Glorious, lake view. Beach access. Relax in this comfortable get-away.
10.0 out of 10, Exceptional, 12 reviews
"I don’t have enough good things to say about our stay! This home is lovely with all of the little amenities that you could think of or want. The master bedroom was my favorite room. It’s complete with a fully adjustable bed and the most comfortable pillows and blankets. The mini library and sitting area were perfect for reading or just relaxing. It’s also where are 13-year old son came every evening to just sit and talk with mom and dad. This was the best part of our trip! The views from the...
Glorious, lake view. Beach access. Relax in this comfortable get-away.
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
Property grounds
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
10.0 out of 10, Exceptional, 1 review
"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
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
On the beach, sun loungers
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
10.0 out of 10, Exceptional, 180 reviews
"Truly above and beyond our expectations. Idyllic location on the shore of Lake Erie. Completely equipped and perfectly clean. Would like to visit again."
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
3 bedrooms, desk, iron/ironing board, internet
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
10.0 out of 10, Exceptional, 2 reviews
"The property was beautiful and very warming! The property manager was extremely polite and helpful with any questions or issues. Overall my kids couldnt have had a better time being at the property and loved sitting on the inlet watching the ducks, beavers and geese every evening! Definitely recommend staying here if your traveling near Mayville."
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
Spectacular Lake Erie Sunsets with beach access
Beach towels
Spectacular Lake Erie Sunsets with beach access
10.0 out of 10, Exceptional, 56 reviews
"We stayed here for a graduation party and this house did not disappoint. The location was right across from the Lake Erie and the views were amazing. We sat out on the big front porch and enjoyed every minute! Thank you for an amazing time!"
Spectacular Lake Erie Sunsets with beach access
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Property grounds
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
10.0 out of 10, Exceptional, 1 review
"A very pleasant and quiet property on the lake. "
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Beach
Cozy 2 Bedroom Canal Front Cottage With Private Dock
9.8 out of 10, Exceptional, 26 reviews
"Awesome"
The price is $125
$257 total
includes taxes & fees
Jun 20 - Jun 21
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Property grounds
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
7.0 out of 10, Good, 2 reviews
"Excellent property, location, and host. Rachel was very friendly and responsive. Thank you!"
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Property grounds
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
9.6 out of 10, Exceptional, 110 reviews
"We were pleased with the unit and the location. The only drawback was the gazebo had rusted scaffolding stored around it that took away any thoughts of enjoying it in the evening. That’s why we only gave the online listing three stars instead of five."
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
Exterior
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
10.0 out of 10, Exceptional, 214 reviews
"Been going to Chautauqua for years and never want to leave. The Chalet is tucked away and not far from the boat launch for fishing. Lots of Chipmunks to keep you entertained. Recommend"
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
Darling Cottage ~ 1 Mi to Lake Erie Beach!
Fridge, microwave, stovetop, coffee/tea maker
Darling Cottage ~ 1 Mi to Lake Erie Beach!
9.4 out of 10, Exceptional, 13 reviews
"This cottage was exaclty as pictured. Very comfortable and clean Would definetly recommend."
Darling Cottage ~ 1 Mi to Lake Erie Beach!
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Microwave, oven, stovetop, dishwasher
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
10.0 out of 10, Exceptional, 2 reviews
"Lovely home located on Sparkling ponds winery property! The house has 3 bedrooms (all queen beds) and 2 full baths with a nice size kitchen (with so many amenities), dining room table for 4 and another area for 2 to dine. The kitchen bing room has a nice layout and the first room as you enter the home. We also enjoyed the gas grill and outdoor dining table. The front porch also has seating where we enjoyed more coffee. Sheets, towels, toiletries, extra blankets, were all included. Communication...
The price is $185
$325 total
includes taxes & fees
Jun 20 - Jun 21
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Bemus Point Lake Front Cottage with Dock
Beach nearby
Bemus Point Lake Front Cottage with Dock
9.8 out of 10, Exceptional, 55 reviews
"Perfect cottage and location for a Chautauqua vacation"
Bemus Point Lake Front Cottage with Dock
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
Interior
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
8.0 out of 10, Very Good, 12 reviews
"My brother and I made this reservation to honor our father who passed away in in 2021. The cabin was perfect because of his love for the outdoors including its location nestled in a quiet cove. The cabin is definitely rustic. It had everything we needed including a beautiful view, and peaceful atmosphere. Plenty of firewood and the necessities for those who enjoy simplicity. The shower is quite small for tall people and hot water spare but served its purpose. We took advantage of the kayaks that...
The price is $299
$471 total
includes taxes & fees
Jul 11 - Jul 12
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
Charming Resort in the Heart of Bemus Village on CHQ Lake
Property grounds
Charming Resort in the Heart of Bemus Village on CHQ Lake
10.0 out of 10, Exceptional, 153 reviews
"Our group of friends have known each other for over 55+ years and this gathering took us back to those wonderful years so long ago. The house was perfect for the 6 of us. Restaurants were within walking distance as was the lake. Debra was helpful with any questions we had."
Charming Resort in the Heart of Bemus Village on CHQ Lake
Lakefront Log Cabin Retreat
Pool
Lakefront Log Cabin Retreat
9.6 out of 10, Exceptional, 18 reviews
"we loved staying here, the cabin was perfect , plenty of room. and the large property allows for plenty of privacy ."
Lakefront Log Cabin Retreat
Don't see what you're looking for?
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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

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, 7 reviews
"great place to stay, unwind and relax. will go back for sure! very clean and well stocked, great location to wineries and restaurants."
The price is $207
$303 total
includes taxes & fees
Jul 8 - Jul 9
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Chautauqua Harbor Hotel - Jamestown
Exterior
Chautauqua Harbor Hotel - Jamestown
3.5 star property
9.6 out of 10, Exceptional, 1,000 reviews
"Great time, can't wait to go back"
The price is $229
$258 total
includes taxes & fees
Jun 23 - Jun 24
Chautauqua Harbor Hotel - Jamestown
Clarion Hotel Conference Center on Lake Erie
Lobby
Clarion Hotel Conference Center on Lake Erie
2.5 star property
7.8 out of 10, Good, 747 reviews
"Nice location on the shores of Lake Erie. Booked a wake up call and it never happened; almost missed an early appointment."
The price is $119
$135 total
includes taxes & fees
Jun 23 - Jun 24
Clarion Hotel Conference Center 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.

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 $125 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 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

Athenaeum Hotel

Athenaeum Hotel

5/5 Excellent
"Great"
A verified traveler stayed at Athenaeum Hotel
Posted 1 day ago
Athenaeum Hotel