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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
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$1,393
HK$2,108 total
includes taxes & fees
17 Nov - 18 Nov
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.
Terrace/patio
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
10.0 out of 10, Exceptional, (34)
"We had a wonderful getaway at this lovely house on the lake! Everything was as described or better. We cooked a couple dinners and found the kitchen had everything we needed. The master bedroom is beautiful with its view of the lake and we appreciated the seasonal decor throughout the house. We spent a lot of time out on the deck enjoying the sound of the waves. We will definitely be back!"
Enjoy fall on the lake - colorful leaves, the grape harvest. Treat yourself.
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, (238)
"Just what we needed to recharge. So beautiful and peaceful. Can't wait to come back."
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
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, (86)
"Beautiful home with all of the amenities as a home base for the Erie Wine Country Fall Harvest Festival!! Perfect weekend!"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
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
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, (14)
"My husband and I had a wonderful weekend celebrating our 33rd anniversary. The cottage was wonderful. The little touches mean so much. From the coffee and flavored creamer to the fall decorations, everything was perfect. The staff at the winery was delightful, not to mention the free bottle of wine! Hopefully we will be back next year! Thank you!"
The price is HK$1,440
HK$2,560 total
includes taxes & fees
16 Nov - 17 Nov
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
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, (12)
"Great place!!! Very roomy and lots of sleeping areas & room for all of us to hangout together "
The price is HK$1,113
HK$4,519 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Interior
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
10.0 out of 10, Exceptional, (191)
"Great stay as always. Thanks Dave!"
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Cozy 2 Bedroom Canal Front Cottage With Private Dock
Miscellaneous
Cozy 2 Bedroom Canal Front Cottage With Private Dock
9.8 out of 10, Exceptional, (33)
"Cute little cottage is a perfect place to stay while at Lake Chautauqua! It was our first trip to the area and the location of the cottage made it easy for us to explore. Communication with the owner was excellent! Would highly recommend and would stay here again if we return to the area."
The price is HK$770
HK$1,759 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom Canal Front Cottage With Private Dock
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$1,114 total
includes taxes & fees
18 Nov - 19 Nov
Step back in time farm house
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, (166)
"Great people and an unbelievable house!"
The price is HK$1,868
HK$3,758 total
includes taxes & fees
17 Nov - 18 Nov
Charming Resort in the Heart of Bemus Village on CHQ Lake
Easy driving distance to local Ski Resorts. Heart of Snowmobile trails!
Fridge, microwave, oven, stovetop
Easy driving distance to local Ski Resorts. Heart of Snowmobile trails!
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"
Easy driving distance to local Ski Resorts. Heart of Snowmobile trails!
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, (227)
"Excellent"
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
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
Casa Andante - Lakefront Escape
Miscellaneous
Casa Andante - Lakefront Escape
10.0 out of 10, Exceptional, (53)
"Great location, house was perfect for our friends get together. Beautiful views of the lake! Kitchen is well stocked, and the women loved the wine glasses. House is nicely decorated and very spacious! We had a great time sitting around the fire pit during the evening and enjoyed the morning sunrise. We will definitely be back! "
The price is HK$3,015
HK$6,395 total
includes taxes & fees
19 Nov - 20 Nov
Casa Andante - Lakefront Escape
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
Lakehouse Vineyard on Lake Erie!
Exterior
Lakehouse Vineyard on Lake Erie!
9.4 out of 10, Exceptional, (21)
"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!
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"
The price is HK$794
HK$1,549 total
includes taxes & fees
16 Nov - 17 Nov
Pet Friendly home by the Stow Ferry
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
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
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$1,393
HK$2,108 total
includes taxes & fees
17 Nov - 18 Nov
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, (1001)
"Overall this hotel was incredible and we had a wonderful stay. My only complaint is that it’s been two weeks and I still have not gotten my damage deposit back. It is still “pending”! I have never had a hold take this long to be released. That is my only complaint. "
The price is HK$1,052
HK$1,188 total
includes taxes & fees
17 Nov - 18 Nov
Chautauqua Harbor Hotel - Jamestown
Best Western Dunkirk & Fredonia Inn
Desk, laptop workspace, iron/ironing board, free cots/infant beds
Best Western Dunkirk & Fredonia Inn
2.5 star property
7.8 out of 10, Good, (876)
"Great place to stay, HOWEVER the lady at the front desk chased me into the parking lot fussing about my keys, which were in my room for pickup. Chill out fussy grandma, don't chase guests out to their car in the AM. You were a negative note on a great stay!"
The price is HK$840
HK$950 total
includes taxes & fees
28 Nov - 29 Nov
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?

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.