Photo by Matthew Jay

Portland Holiday Rentals

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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, (21)
"Very pretty cottage nestles right by Lake Erie! Highly recommend. Will def book again when we bring our dog along. Owner was very cooperative and great communication. "
The price is HK$1,392
HK$2,099 total
includes taxes & fees
6 Jan - 7 Jan 2025
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
On the beach, sun-loungers

Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining

10.0 out of 10, Exceptional, (239)
"Came out on a fishing trip and was very pleased. Very nice very clean and well equipped. Might bring my wife out for a long weekend next summer. I highly recommend this property. You will not be disappointed if you book a stay here. "
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
Terrace/patio

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

10.0 out of 10, Exceptional, (38)
"The property was great for our Thanksgiving get-together. The view of Lake Erie is wonderful, the house is comfortable and well-appointed (with a great kitchen), and our hosts were excellent. In fact, the owner (Ethan) really went above and beyond. We were unexpectedly snowed in by a lake-effect storm, and Ethan reached out to a neighbor who brought us pizza and wine! Just terrific people all the way around. A heartfelt thanks to all. We would definitely return to the Lake House!"
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
Lakehouse Vineyard on Lake Erie!
Exterior

Lakehouse Vineyard on Lake Erie!

9.2 out of 10, Wonderful, (22)
"Short family getaway to watch our daughter play tennis at a nearby college. Would vome again forca winery tour. We were able to visit 4, but there are so many more in the area. If you like sweet wine and wine tastings, this a a great place to be. Property is gorgeous! Lots of big spiders, but only on the outside. Host wad super accomodating. Operyy"
Lakehouse Vineyard on Lake Erie!
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (13)
"Very nice spacious house. Very centrally located for our wine tour. Only complaint is the wifi was not good. "
The price is HK$1,104
HK$4,507 total
includes taxes & fees
24 Dec - 25 Dec
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Year-Round Renovated Lakefront Cottage & Pet Friendly!

Year-Round Renovated Lakefront Cottage & Pet Friendly!

9.8 out of 10, Exceptional, (183)
"Lovely home on Chautauqua Lake. Picture perfect fall weather, bonfires and fall foliage!"
Year-Round Renovated Lakefront Cottage & Pet Friendly!
Beautiful Pet friendly cottage by the Stow Ferry
Property grounds

Beautiful Pet friendly cottage by the Stow Ferry

9.6 out of 10, Exceptional, (27)
"Super clean! Plenty of towels!!! We enjoyed our stay"
The price is HK$816
HK$1,588 total
includes taxes & fees
4 Jan - 5 Jan 2025
Beautiful Pet friendly cottage by the Stow Ferry
Designer Home in the Middle of Wine Country is BACK!
Fridge, microwave, oven, stovetop

Designer Home in the Middle of Wine Country is BACK!

10.0 out of 10, Exceptional, (43)
"Comfortable home in quiet neighborhood. Stayed here last year. Beautiful decor, Perfect for all our needs"
Designer Home in the Middle of Wine Country is BACK!
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, (88)
"Fantastic property!!! Clean, spacious, and inviting!! The girls and I enjoyed a beautiful weekend!! Thank you!!"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Private Home: Lightkeeper's Refuge steps to beach, marina and boat slip
Beach nearby, beach towels

Private Home: Lightkeeper's Refuge steps to beach, marina and boat slip

9.8 out of 10, Exceptional, (36)
"With a vineyard and garden in the backyard this house is perfect. We were able to watch restoration of the lighthouse across the street and had a wonderful view of Lake Erie. The house is also perfectly located for quick day trips to Buffalo, Niagara, and Chautauqua. "
Private Home: Lightkeeper's Refuge steps to beach, marina and boat slip
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Miscellaneous

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 HK$770
HK$1,757 total
includes taxes & fees
5 Jan - 6 Jan 2025
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Pet Friendly home by the Stow Ferry
Fridge, microwave, oven, stovetop

Pet Friendly home by the Stow Ferry

9.6 out of 10, Exceptional, (22)
"The place was overall comfortable, but left a little to be desired in expectation. It's the shoulder season and freezing at night. We didn't arrive until after dark and it was 53 inside. I was raised not to go to sleep with electric space heaters on, but that seemed to be the only working provision. The gas did not appear to be turned on"
Pet Friendly home by the Stow Ferry
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, (15)
"Property was nice, but we only got to stay 1 of the 2 nights due to extreme snow. We were stuck elsewhere while our belongings were at the rental. Owner was understanding and helpful in getting them back once the road was cleared.. Overall rating would have been 4.5 if that were an option"
The price is HK$1,439
HK$2,558 total
includes taxes & fees
24 Dec - 25 Dec
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

9.6 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
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Interior

True Lake Beachfront, Stunning Sunsets, Beach glass hunting

10.0 out of 10, Exceptional, (193)
"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
Step back in time farm house
Fridge, microwave, oven, stovetop

Step back in time farm house

9.8 out of 10, Exceptional, (43)
"Comfy beds and pillows, lots of room, full kitchen, quiet and relaxing. Findley Lake is a nice little village, Alexanders is a great place to have a beer and some food. "
The price is HK$537
HK$1,113 total
includes taxes & fees
6 Jan - 7 Jan 2025
Step back in time farm house
Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly
Beach

Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly

10.0 out of 10, Exceptional, (171)
"Wonderful facilities and property. Location is great too!"
Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly
Cozy Getaway ON Lake Erie
Terrace/patio

Cozy Getaway ON Lake Erie

9.8 out of 10, Exceptional, (116)
"We all had a great time!! Fishing, bird photography along the lake, dinner outside with beautiful view of lake Erie. Kids enjoyed the playground and skipping rocks. "
Cozy Getaway ON Lake Erie
Spectacular Lake Erie Sunsets with beach access
Beach towels

Spectacular Lake Erie Sunsets with beach access

10.0 out of 10, Exceptional, (72)
"This was our second time staying at the amazing Lake House! Can’t wait to go back!"
Spectacular Lake Erie Sunsets with beach access
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Miscellaneous

Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

8.4 out of 10, Very good, (8)
"Perfect little cabin in a great location. Good price and have no complaints. Thank you"
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
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
Terrace/patio

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

10.0 out of 10, Exceptional, (21)
"Very pretty cottage nestles right by Lake Erie! Highly recommend. Will def book again when we bring our dog along. Owner was very cooperative and great communication. "
The price is HK$1,392
HK$2,099 total
includes taxes & fees
6 Jan - 7 Jan 2025
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, (1000)
"Great restaurant!"
The price is HK$919
HK$1,038 total
includes taxes & fees
5 Jan - 6 Jan 2025
Chautauqua Harbor Hotel - Jamestown
Best Western Dunkirk & Fredonia Inn
Exterior

Best Western Dunkirk & Fredonia Inn

2.5 star property
7.8 out of 10, Good, (886)
"We didn’t plan on staying at Best Western in Dunkirk NY but were forced to exit I-90 west bound due to closure of freeway due to snow storm. The short notice booking charge for first night was $300.00 CAD and second night $198.00 USD plus tax for an average room.with kingsize bed. Honestly the pricing was ridiculously expensive but no choice due to weather "
The price is HK$840
HK$949 total
includes taxes & fees
5 Jan - 6 Jan 2025
Best Western Dunkirk & Fredonia 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?

Lakefront Cottage Home for All Seasons Enjoyment on Beautiful Lake Erie!: This holiday home rental outside of Portland is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Portland?

While exploring the area, visit family-friendly sights like Chautauqua Bookstore, 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.