Photo by Matthew Jay

Holiday Rentals in Portland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Portland

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

10.0 out of 10, Exceptional, (22)
"After reading the other reviews, we booked this cottage and boy did it deliver! Amazing views, a hammock, firepit, and a perfect sun porch for reading, that we will return to enjoy in warmer weather. Inside, everything has been thought of and we wanted for nothing. We enjoyed being able to bring our dog, as well. Julie was attentive and quick to respond to any inquiries we had. You will not be disappointed so book it already!pup"
The price is €244
includes taxes & fees
23 Feb - 24 Feb
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.

10.0 out of 10, Exceptional, (40)
"We had a very nice stay in a beautiful home from which we watched and heard the arctic blast freeze Lake Erie. Perfect place to appreciate something we’d never seen before. "
The price is €336
includes taxes & fees
4 Mar - 5 Mar
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.

Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

10.0 out of 10, Exceptional, (227)
"Excellent"
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

Waterfront Chautauqua Lake Home w/ Stunning Views

10.0 out of 10, Exceptional, (12)
"Work and vaca. Cottage was perfect."
Waterfront Chautauqua Lake Home w/ Stunning Views

Modern 300 ft lakefront with pool

9.6 out of 10, Exceptional, (89)
"The location of this waterfront property at the north end of Chautauqua Lake is exceptional! The house is large, and although we were only a group of 6, it could accommodate many more. We enjoyed spectacular sunsets, charming campfires, a pontoon boat rental, winery tours, and a quaint lunch and dinner in the town of Mayville. The weather and fall colors could not have been more perfect! "
Modern 300 ft lakefront with pool

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

9.6 out of 10, Exceptional, (16)
"Myself and 5 others stayed at the cottage, it was very clean and cozy. Xinni was accommodating to our needs and answered very quickly. Would definitely stay there again!"
The price is €323
includes taxes & fees
23 Feb - 24 Feb
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

Beautiful Lake House in Point Chautauqua- Available Year Round! NEW BUNK ROOM

9.8 out of 10, Exceptional, (36)
"We had 9 in our group (5 adults and 4 children). There was more than enough room for all of us. The property is well maintained in a quiet private community. We had all the cooking supplies we needed to celebrate our Thanksgiving. The pool table, ping pong table and hot tub out back are an added bonus. The host is extremely responsive. We would definitely come back. Especially in warmer months. Thanks Kate. "
Beautiful Lake House in Point Chautauqua- Available Year Round! NEW BUNK ROOM

Lakehouse Vineyard on Lake Erie!

9.2 out of 10, Wonderful, (24)
"The house was perfect for us. Enough bedrooms, 2 bathrooms, nice kitchen and dining area. Dining area great for playing games. Close to some awesome wineries, close to friends in the area, short drive to Erie. Lake views, gorgeous sunset one nlght, typical snow storm one night. We had a wonderful time sightseeing, even in the middle of winter! My only suggesting is to get the names and numbers of the 2 owners before you get there. VRBO is frustrating to work with. "
Lakehouse Vineyard on Lake Erie!

"The Grape Escape"-Stylish Retreat Wine Country PA

9.0 out of 10, Wonderful, (12)
"AMAZING WEEKEND!! Amazing place!!! The place was even more awesome in person than on line! Big and spacious, beautiful setting, great spaces!!! Would define stay again!! "
"The Grape Escape"-Stylish Retreat Wine Country PA

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

10.0 out of 10, Exceptional, (172)
"This is a very nice property in a beautiful lake setting. Everything about this place and our stay was perfect. "
Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake

True Lake Beachfront, Stunning Sunsets, Beach glass hunting

10.0 out of 10, Exceptional, (195)
"This cabin, right on the lake, is the perfect location to spend time in the area no matter the time of year. My wife and I spent the weekend visiting the area and taking in the winter activities. We had everything we needed in this very clean and well stocked cabin. The views of the frozen lake from the comfort of a cozy family room sealed the deal. We were told by locals to come back and visit in the summer for a whole different experience. If we return, we know we have a great place to...
True Lake Beachfront, Stunning Sunsets, Beach glass hunting

Bemus Point Lake Front Cottage with Dock

9.6 out of 10, Exceptional, (71)
"Loved the lake view, great parking also. Very peaceful, I enjoyed every minute."
Bemus Point Lake Front Cottage with Dock

Waterfront Cottage - Dock & Chautauqua Lake Access

9.0 out of 10, Wonderful, (2)
"This property was so relaxing. We had everything we needed. The owners were quick to reply when needed and super friendly. I didn’t want to leave."
Waterfront Cottage - Dock & Chautauqua Lake Access

Lakeview Cabin with hot tub and located close to wineries

9.8 out of 10, Exceptional, (8)
"the house was cute as can be, very nicely decorated, and stocked with good kitchen ware and supplies"
Lakeview Cabin with hot tub and located close to wineries

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

10.0 out of 10, Exceptional, (11)
"very nice, cozy house with plenty of room "
The price is €630
includes taxes & fees
23 Feb - 24 Feb
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Big Barn in Bemus Point, unique, peaceful, and memorable

10.0 out of 10, Exceptional, (4)
"Words can explain how amazing this place is. Everything about it is top notch - I could write a book on how awesome it is 😊😎😊😎 we weee able to fit 13 people so comfortably and never felt like we were under each others feet . Weather allowed us to be outside for cornhole and ladder ball during the afternoon and beautiful campfires at night ! None of our group had anything negative to say about any of our stay . LOVED it and will be returning at some point ! Thank you Emily and Greg ! "
Big Barn in Bemus Point, unique, peaceful, and memorable

Bemus Point Vacation Rental

8.6 out of 10, Excellent, (103)
"Our cottage was adorable!!! Everything was very accommodating, cabinets fully stocked, comfortable beds, beautiful lake view and close proximity to everything we were there for. We can’t wait to come back!"
Bemus Point Vacation Rental

Spacious 7-bedroom Lake House - 50' from Lake Erie

Spacious 7-bedroom Lake House - 50' from Lake Erie

Darling Cottage ~ 1 Mi to Lake Erie Beach!

10.0 out of 10, Exceptional, (22)
"Cottage was fantastic. Great location. Perfect for our needs. Very clean and had everything we needed. We will definitely stay here again. "
Darling Cottage ~ 1 Mi to Lake Erie Beach!

Lake Life Luxury Home on Chautauqua Lake

10.0 out of 10, Exceptional, (5)
"This house on the lake was perfect for our weekend getaway! The view was amazing and my favorite part of the day, was making coffee and walking out to the end of the dock, watching the water glisten…it was so peaceful and relaxing. We will definitely be coming back here for another stay! Thank you so much!"
Lake Life Luxury Home on Chautauqua Lake
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.
Don't see what you're looking for?
See all available properties in Portland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Portland you may be interested in

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

10.0 out of 10, Exceptional, (22)
"After reading the other reviews, we booked this cottage and boy did it deliver! Amazing views, a hammock, firepit, and a perfect sun porch for reading, that we will return to enjoy in warmer weather. Inside, everything has been thought of and we wanted for nothing. We enjoyed being able to bring our dog, as well. Julie was attentive and quick to respond to any inquiries we had. You will not be disappointed so book it already!pup"
The price is €244
includes taxes & fees
23 Feb - 24 Feb
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Chautauqua Harbor Hotel - Jamestown

3.5 star property
9.6 out of 10, Exceptional, (1003)
"We came down for a little overnight getaway, just to rest, relax and got exactly what we needed. Had a couple drinks at the bar. The bartender custom made a cranberry martini for me that was fantastic! The we had a delicious dinner and a beautiful night of rest and relaxation in a comfortable and well appointed room!"
The price is €128
includes taxes & fees
3 Mar - 4 Mar
Chautauqua Harbor Hotel - Jamestown

Quality Inn

2.5 star property
7.6 out of 10, Good, (417)
"Very friendly staff! Checked in to a king room but it smelled like stale smoke (possibly because it was once a smoking room). Front desk apologized and switched us to another room. Easy peasy fix! "
The price is €105
includes taxes & fees
23 Mar - 24 Mar
Quality Inn
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.

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portland has to offer?

Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.: This holiday home rental outside of Portland is located on a lake, and has a balcony, a selection of games and a BBQ 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 wider area, you’ll find 21 Brix Winery and Lake Erie State Park.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip.