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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, (45)
"We had a great time!"
The price is NZ$617
includes taxes & fees
9 Oct - 10 Oct
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, (79)
"I would highly recommend this property for the perfect view of the lake on the deck and from the main bedroom, the cleanliness, and easy access to the quaint downtown of North East. Our stay couldn’t have been better! "
Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

Beachfront Retreat in Wine Country w/ Sunset View!

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great place to stay. Plenty of games for the kids to use.Very well stock with supply's like soap paper products ect. Great serenity."
The price is NZ$1,562
includes taxes & fees
28 Oct - 29 Oct
Beachfront Retreat in Wine Country w/ Sunset View!

Charming Resort in the Heart of Bemus Village on CHQ Lake

10.0 out of 10, Exceptional, (192)
"Location was perfect for us, place was clean and well stocked with everything we needed. Hosts were available to answer any questions we had. "
The price is NZ$855
includes taxes & fees
12 Oct - 13 Oct
Charming Resort in the Heart of Bemus Village on CHQ Lake

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

10.0 out of 10, Exceptional, (243)
"Really great place to get away from it all, my Family truly enjoyed our time there. "
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

Cozy stay on 10acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.

2.0 star property
9.6 out of 10, Exceptional, (9)
"Awesome place. Quant and quiet. "
The price is NZ$439
includes taxes & fees
9 Oct - 10 Oct
Cozy stay on 10acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.

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

10.0 out of 10, Exceptional, (111)
"We enjoyed our stay. The property was lovely. "
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Beautiful Pet friendly cottage by the Stow Ferry

9.6 out of 10, Exceptional, (35)
"We enjoyed our stay very much. Simple but well maintained. We would stay here again. "
Beautiful Pet friendly cottage by the Stow Ferry

Modern 300 ft lakefront with pool

9.6 out of 10, Exceptional, (97)
"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

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

9.8 out of 10, Exceptional, (30)
"7 friends stayed for a girls getaway weekend. The location was excellent and the house was fully equipped. We would definitely rent it again!"
The price is NZ$747
includes taxes & fees
10 Oct - 11 Oct
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

Step back in time farm house

9.6 out of 10, Exceptional, (67)
"Very nice place! Love the spin on the antiques! Enjoyed our time her."
The price is NZ$238
includes taxes & fees
9 Oct - 10 Oct
Step back in time farm house

Create your family memories at our nautical lakeside home!

10.0 out of 10, Exceptional, (138)
"We had an incredible holiday week at Lorraine’s home! We loved all the extra water toys as much as our kids did. Staying there truly felt like being at our own home. It was extremely spacious which gave us all space to comfortably spread out after a long day on the lake. Would love to stay again!"
Create your family memories at our nautical lakeside home!

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

8.8 out of 10, Excellent, (11)
"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

LAKEFRONT PRIVACY ON SUNSET COVE

10.0 out of 10, Exceptional, (79)
"Breathtaking views and outside space was incredible! Loved all the different spots you could sit to admire Lake Eries beauty! "
LAKEFRONT PRIVACY ON SUNSET COVE

Bemus Point Lake Front Cottage with Dock

9.6 out of 10, Exceptional, (85)
"Great location for our needs and a very well-stocked cottage!"
Bemus Point Lake Front Cottage with Dock

Secluded Cottage with Hidden Cove on Lake Erie

10.0 out of 10, Exceptional, (17)
"We really enjoyed our stay. The location is amazing and there's lots to do close by. Sitting by the water watching the sunset with a bottle of local wine was the highlight."
Secluded Cottage with Hidden Cove on Lake Erie

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

9.6 out of 10, Exceptional, (20)
"We had all the aunties, uncle's and cousins for a few days of skiing. Great house, located close to Peekn Peak"
The price is NZ$1,128
includes taxes & fees
20 Oct - 21 Oct
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

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

9.6 out of 10, Exceptional, (15)
"The property is so beautiful and worth the stay. Our hosts were so accommodating, even brought by some K-cups cause they remembered there were only a few left. We would definitely stay again!"
Superb 3-bedroom, 2 bath house on lake erie. 2 min drive to Barcelona Harbor!

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

9.6 out of 10, Exceptional, (30)
"Very clean and well equipped, great attention to detail. We would love to come back."
The price is NZ$574
includes taxes & fees
9 Oct - 10 Oct
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

Lakefront Log Cabin Retreat

9.8 out of 10, Exceptional, (28)
"Very roomy and clean. Our visit was cut short."
Lakefront Log Cabin Retreat
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$238 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 holiday 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 holiday.

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 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. Or, Winter snuggle.: 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 Lily Dale Spiritual Center.

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.