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Portland Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Portland

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

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 HK$1,611
HK$2,770 total
includes taxes & fees
19 Oct - 20 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.
Interior

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!
Property grounds

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 HK$3,603
HK$7,053 total
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
Marina

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 HK$1,681
HK$3,869 total
includes taxes & fees
13 Oct - 14 Oct
Charming Resort in the Heart of Bemus Village on CHQ Lake
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, (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
Beautiful Pet friendly cottage by the Stow Ferry
Property grounds

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

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 HK$973
HK$1,981 total
includes taxes & fees
10 Oct - 11 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!
Marina

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!
Step back in time farm house
Fridge, microwave, oven, stovetop

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 HK$567
HK$1,169 total
includes taxes & fees
20 Oct - 21 Oct
Step back in time farm house
Create your family memories at our nautical lakeside home!
Property grounds

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!
Modern 300 ft lakefront with pool
Pool

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

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
Beach

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
Property grounds

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
On the beach

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
Interior

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 HK$1,590
HK$5,092 total
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!
Outdoor dining

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
Microwave, oven, stovetop, dishwasher

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 HK$1,296
HK$2,581 total
includes taxes & fees
18 Oct - 19 Oct
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!
Exterior

Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!

10.0 out of 10, Exceptional, (22)
"We had a wonderful time at this perfectly appointed property. The host is very accommodating. Everything designed to ensure a lovely and relaxing time on this beautiful property."
The price is HK$1,723
HK$4,216 total
includes taxes & fees
12 Oct - 13 Oct
Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!
Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake
Beach

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

10.0 out of 10, Exceptional, (182)
"House was great no complaints "
Enjoy a 4-bedroom vacation home with 75 feet of lake frontage 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.
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Top Portland Hotel Reviews

The White Inn

The White Inn

10/10 Excellent
"The room was gorgeous, bed comfortable, staff was amazing. Great location with a cute bar/dining. "
Christine 1-night trip
Posted 5 days ago
The White Inn

Find out more about Portland

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

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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.