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Portland Holiday Rentals

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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 AU$395
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 AU$542
includes taxes & fees
23 Feb - 24 Feb
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

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 AU$522
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)
"Lovely spot for fishing and local recreation. Near creek shoreline recently restored and stabilized with tree plantings which is ideal for trout fishing. House has everything you’d want for modern cabin. Come and you’ll want to return again. "
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 AU$1,020
includes taxes & fees
20 Feb - 21 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

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!

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

10.0 out of 10, Exceptional, (91)
"This was a great place for a girls weekend! House is beautiful, very well kept and right on the lake. Walking distance to bemus point tap house. Debra was great with checking in on us and making sure we had everything we needed. "
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Stunning Vacation retreat. Heated pool, ideal for family vacations or friends.

10.0 out of 10, Exceptional, (10)
"The property was wonderful. The house was comfortable and very clean. Had everything our group needed for a great weekend. The Host responsive. Hope to rent again"
The price is AU$614
includes taxes & fees
2 Mar - 3 Mar
Stunning Vacation retreat. Heated pool, ideal for family vacations or friends.

Cozy 2 Bedroom Canal Front Cottage With Private Dock

9.6 out of 10, Exceptional, (35)
"Very nice getaway for late fall. Basically had the area to ourselves. Nice and quiet with plenty eateries still open."
The price is AU$355
includes taxes & fees
23 Feb - 24 Feb
Cozy 2 Bedroom Canal Front Cottage With Private Dock
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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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 AU$395
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, (1001)
"I have to say this is my favorite hotel in the Chautauqua area. They have great hotel packages, swimming pool, gym and in the summer they have a pool outside and a outside bar. Inside their restaurant offers a variety of food and drinks. Great place to hang out. Their accommodations are clean, bed is comfortable and they have rooms with a porch where you can see the beautiful view of Chautauqua lake. They also have great events."
The price is AU$210
includes taxes & fees
2 Mar - 3 Mar
Chautauqua Harbor Hotel - Jamestown

Quality Inn

2.5 star property
7.6 out of 10, Good, (416)
"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 AU$172
includes taxes & fees
19 Mar - 20 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.