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Portland Holiday Rentals

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Holiday Rentals in Portland

Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (5)
"Great property in a great location! We enjoyed our 1 night stay and would definitely return!"
The price is NZ$491
per night
28 May - 29 May
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Property grounds
Luxe Cabin /Hot Tub / EV Charger
10.0 out of 10, Exceptional, (12)
"Property was exactly as shown in the pictures. The cabins were delightful, beautiful wooden views. Lots of amenities in the main house and everything was super clean. Check-in was easy and the hosts were very communicative. Close to hiking, wineries, breweries, and Chautauqua."
Luxe Cabin /Hot Tub / EV Charger
Property grounds
Glorious, lake view. Beach access. Relax in this comfortable get-away.
10.0 out of 10, Exceptional, (8)
"Ethan's home on Lake Erie is amazing. The location was great. The views were awesome. The house is as pictured but better! Very clean, comfortable, and well stocked. They have thought of everything. Communication and check in was extremely easy. Thank you for sharing this lovely home. We will definitely be back."
Glorious, lake view. Beach access. Relax in this comfortable get-away.
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Property grounds
Lake Erie Waterfront in Chautauqua Wine Region
9.8 out of 10, Exceptional, (24)
"The house and grounds are absolutely beautiful. The setting is rural and quiet, and the large deck on the back of the house is a wonderful gathering space for family and friends. The kitchen was well appointed with everything that we needed, and the decor throughout the house was pleasing."
Lake Erie Waterfront in Chautauqua Wine Region
Beach towels
Spectacular Lake Erie Sunsets with beach access
10.0 out of 10, Exceptional, (54)
"My mother and I went for a mother/daughter trip over Mother's Day weekend. We had an amazing time. We had a warm welcome message upon entering the lake house which was so sweet. We had everything we could have possibly needed right at our finger tips. Stacy is gracious enough to think of absolutely everything! The view of the lake from the front deck is lovely, and the sunsets are absolutely gorgeous. We were able to see the Northern Lights and it was amazing. Stacy is a great host and so very...
Spectacular Lake Erie Sunsets with beach access
Fridge, microwave, oven, stovetop
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
10.0 out of 10, Exceptional, (1)
"Excellent property, location, and host. Rachel was very friendly and responsive. Thank you!"
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Beach nearby
Bemus Point Lake Front Cottage with Dock
9.8 out of 10, Exceptional, (51)
"The property met our needs except there were no tv stations. I guess you have to know how to do streaming and apps which we do not do. We were there to visit our son and daughter in law who live outside Jamestown and it was a great location, about a 15 minute drive to their house. We had a great time."
Bemus Point Lake Front Cottage with Dock
Property grounds
Chautauqua private acreage. Centrally located with your own heated pool to enjoy
10.0 out of 10, Exceptional, (1)
"Couldn’t have asked for a better property for our stay. The owners are super nice and thoughtful as well! 100% recommend this house for your stay in this area."
Chautauqua private acreage. Centrally located with your own heated pool to enjoy
Exterior
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
10.0 out of 10, Exceptional, (212)
"We’ve been visiting Chautauqua for years and this was by far our best trip yet. The chalet was beautiful and very well stocked with all the essentials and then some!! Communication with the owners was great. We were able to hike and explore the property, play in the snow, enjoy some of the local wineries, then wind down to relax by the cozy fireplace. Our family had an amazing time and is already looking forward to staying here again. Thanks for opening your home to help us create some wonderful...
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
Property grounds
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
10.0 out of 10, Exceptional, (67)
"We had another amazing time. Such a wonderful peaceful beautiful place. Thank you once again for sharing your home with us !"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
On the beach, sun-loungers
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
10.0 out of 10, Exceptional, (180)
"Truly above and beyond our expectations. Idyllic location on the shore of Lake Erie. Completely equipped and perfectly clean. Would like to visit again."
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Fridge, microwave, oven, stovetop
Pet Friendly home by the Stow Ferry
9.8 out of 10, Exceptional, (14)
"This place was perfect. Melinda was a wonderful host and immediately responsive. Great stay! Will definitely stay here again."
Pet Friendly home by the Stow Ferry
Fridge, microwave, stovetop, coffee/tea maker
Darling Cottage ~ 1 Mi to Lake Erie Beach!
10.0 out of 10, Exceptional, (12)
"This cottage was exaclty as pictured. Very comfortable and clean Would definetly recommend."
Darling Cottage ~ 1 Mi to Lake Erie Beach!
Fridge, microwave, stovetop, dishwasher
Charming Lake Erie Getaway: Walk to Beach!
10.0 out of 10, Exceptional, (12)
"Nice quiet home. Will consider staying again in the future"
Charming Lake Erie Getaway: Walk to Beach!
Property grounds
Cozy Getaway ON Lake Erie
9.6 out of 10, Exceptional, (109)
"My Florida family and I stayed for my mom’s funeral. Great place for the family and friends to congregate while we were in town."
Cozy Getaway ON Lake Erie
Property grounds
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
10.0 out of 10, Exceptional, (1)
"We had a wonderful visit at this tiny house on the lake. Beautiful views. The house itself was open and spacious. Ended up we had a few tag alongs and it easily accommodated 6 adults. We will be back again! PS: You can fish from the beach."
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
2 bedrooms, WiFi, bed sheets
Spacious and Modern "Tiny Home" with 2 bedrooms directly on Chautauqua Lake
10.0 out of 10, Exceptional, (1)
"Stayed here for the eclipse but got much more out of it. It was a nice quiet stay right on the lake which made for and enjoyable long weekend. Havinging th abilty to walk out, sit around a fire on a lake and fish was quite enjoyable. The tiny home was perfect for our needs and look forward to staying here again in the future. It was pet friendy yet lacked any animal hair which was a big concern as we had more than 1 person alerigic to dogs but had to bering out non shedding dog with us. Overall...
Spacious and Modern "Tiny Home" with 2 bedrooms directly on Chautauqua Lake
Property grounds
A great view of the lake with many activities within walking distance.
10.0 out of 10, Exceptional, (9)
"We had a wonderful time at Karen and Tim’s property it was everything we wanted and needed it to be. If you are looking for history this house has so much history. The host’s were fantastic and the house was great, well stocked, clean,and what a great location. Would recommend it to anyone. Our whole family had a great time ages 2-60+. Will definitely go back. Shelly B Almond,NY"
A great view of the lake with many activities within walking distance.
On the beach
Secluded Cottage with Hidden Cove on Lake Erie
10.0 out of 10, Exceptional, (3)
"This place was simply amazing. Sunsets were the best, along with the stunning views! We'll definitely be back."
Secluded Cottage with Hidden Cove on Lake Erie
Beach
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
10.0 out of 10, Exceptional, (229)
"Thanks David and Barbara! Again, the accommodations were amazing, and the views and sunsets were beautiful as always! Can't wait to stay again! Thank you Jesse and Jenn."
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
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See all available properties in Portland
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.

Other types of properties in Portland you may be interested in

Property grounds
Luxe Cabin /Hot Tub / EV Charger
10.0 out of 10, Exceptional, (12)
"Property was exactly as shown in the pictures. The cabins were delightful, beautiful wooden views. Lots of amenities in the main house and everything was super clean. Check-in was easy and the hosts were very communicative. Close to hiking, wineries, breweries, and Chautauqua."
Luxe Cabin /Hot Tub / EV Charger
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (5)
"Great property in a great location! We enjoyed our 1 night stay and would definitely return!"
The price is NZ$491
per night
28 May - 29 May
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Exterior
Chautauqua Harbor Hotel - Jamestown
3.5 star property
9.6 out of 10, Exceptional, (1010)
"Best hotel in the area this is my 3rd time staying it is really clean and beautiful scenic area"
The price is NZ$330
per night
28 May - 29 May
Chautauqua Harbor Hotel - Jamestown
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portland. Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portland short-term rentals, that won’t be hard to do.

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?

Glorious, lake view. Beach access. Relax in this comfortable get-away.: 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.

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