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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
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (7)
"We liked the house, it fit our needs for our plans in Erie. The sunset views over the lake were spectacular. Very clean, Julie was a fast with email replies and communication. The gas fireplace on Friday night was nice while overlooking the lake in the evening. Breakfast was easy in the kitchen both mornings, it had everything we needed for the 3 of us. Well thought out layout and a lot of attention to details. My daughter loved soaking in the huge bathtub Saturday night. Sitting on the front...
The price is HK$1,617
HK$2,369 total
includes taxes & fees
28 Jul - 29 Jul
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, (232)
"We love the additions to this cottage from previous years. Perfect! Thank you!"
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Property grounds
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
10.0 out of 10, Exceptional, (70)
"Everything about our stay, the property a the hosts wa amazing. It’s location with the water front location nd walking distance to everything in Bemus Point! Highly recommend!"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
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Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Property grounds
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
9.6 out of 10, Exceptional, (111)
"If you are dealing with the hustle of everyday life and need some time to kick your feet up, have coffee in the morning on the dock at the lake, sit by a campfire at night, wet a line, walk to the quaint little downtown area of Bemus Point for lunch, dinner, wine bar, brewery. This little gem fits the bill! Property owners are awesome! We will definitely be back."
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Casa Andante - Lakefront Escape
Property grounds
Casa Andante - Lakefront Escape
10.0 out of 10, Exceptional, (49)
"Beautiful, clean home. The view was amazing and the amenities were perfect. Our family enjoyed our stay and would definitely recommend staying here."
Casa Andante - Lakefront Escape
Glorious, lake view. Beach access. Relax in this comfortable get-away.
Property grounds
Glorious, lake view. Beach access. Relax in this comfortable get-away.
10.0 out of 10, Exceptional, (12)
"I don’t have enough good things to say about our stay! This home is lovely with all of the little amenities that you could think of or want. The master bedroom was my favorite room. It’s complete with a fully adjustable bed and the most comfortable pillows and blankets. The mini library and sitting area were perfect for reading or just relaxing. It’s also where are 13-year old son came every evening to just sit and talk with mom and dad. This was the best part of our trip! The views from the...
Glorious, lake view. Beach access. Relax in this comfortable get-away.
Lake Front, Spacious, and Modern "Tiny Home" with 2 bedrooms and 1 bathroom
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
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Property grounds
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
10.0 out of 10, Exceptional, (2)
"The cottage was very cute and just as described."
Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Bemus Point Lake Front Cottage with Dock
Beach nearby
Bemus Point Lake Front Cottage with Dock
9.8 out of 10, Exceptional, (57)
"Lots of fishing !!!"
Bemus Point Lake Front Cottage with Dock
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, (168)
"My family of six, including my 4 teen boys as well as my friend and her daughter had a wonderful time here. The cabin has a beautiful view and a nice sized deck and backyard for all kinds of activities. The house was clean and well stocked. The house was big enough to accommodate us comfortably but cozy enough that so much time was spent together. Teenagers have a habit of disappearing on their phones. Instead the days were spent floating and kayaking in the lake or playing yard games. Evenings...
Private Chautauqua Lake House - 75 Ft Lake Front - Dock Available - Pet Friendly
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
3 bedrooms, desk, iron/ironing board, Internet
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and very warming! The property manager was extremely polite and helpful with any questions or issues. Overall my kids couldnt have had a better time being at the property and loved sitting on the inlet watching the ducks, beavers and geese every evening! Definitely recommend staying here if your traveling near Mayville."
Waterfront Chautauqua Lake Retreat: Dock, Kayaks!
Lake Erie Waterfront in Chautauqua Wine Region
Property grounds
Lake Erie Waterfront in Chautauqua Wine Region
9.8 out of 10, Exceptional, (25)
"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
"The Grape Escape"-Stylish Retreat Wine Country PA
Aerial view
"The Grape Escape"-Stylish Retreat Wine Country PA
9.8 out of 10, Exceptional, (6)
"Everything was as described. It was a good meeting place for family members from Pittsburgh, Ohio, Buffalo, Syracuse. Easter weekend. Clean, comfortable"
"The Grape Escape"-Stylish Retreat Wine Country PA
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Fridge, microwave, oven, stovetop
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
10.0 out of 10, Exceptional, (182)
"We absolutely love staying here. The cabin is always so clean and well stocked when we arrive. Dave is such a wonderful host. We book a few trips every year. This is our happy place!"
True Lake Beachfront, Stunning Sunsets, Beach glass hunting
Charming Resort in the Heart of Bemus Village on CHQ Lake
Property grounds
Charming Resort in the Heart of Bemus Village on CHQ Lake
10.0 out of 10, Exceptional, (154)
"Great location. 5 minute walk to all the restaurants. Fully stocked kitchen. Great outdoor space"
Charming Resort in the Heart of Bemus Village on CHQ Lake
Cozy Getaway ON Lake Erie
Property grounds
Cozy Getaway ON Lake Erie
9.6 out of 10, Exceptional, (110)
"The house was well stocked with everything we needed for the weekend and an extra comfy cot that we requested. The location right on the shore was exactly what we wanted but I wish we could have walked further on the shore in each direction. The fire ring was great in the evenings. Overall a fun and chill weekend for our family!"
Cozy Getaway ON Lake Erie
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, (216)
"The perfect place for kids to explore and parents to relax! Very close to midway park and the lake. It was also nice to just stay at the house and enjoy what it has to offer."
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake
Spectacular Lake Erie Sunsets with beach access
Beach towels
Spectacular Lake Erie Sunsets with beach access
10.0 out of 10, Exceptional, (57)
"Amazing stay, beautiful property. The house was clean and everything we needed was available to us. Will definetly book again!"
Spectacular Lake Erie Sunsets with beach access
Darling Cottage ~ 1 Mi to Lake Erie Beach!
Fridge, microwave, stovetop, coffee/tea maker
Darling Cottage ~ 1 Mi to Lake Erie Beach!
9.4 out of 10, Exceptional, (14)
"This cottage was exaclty as pictured. Very comfortable and clean Would definetly recommend."
Darling Cottage ~ 1 Mi to Lake Erie Beach!
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
Interior
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
8.0 out of 10, Very good, (12)
"My brother and I made this reservation to honor our father who passed away in in 2021. The cabin was perfect because of his love for the outdoors including its location nestled in a quiet cove. The cabin is definitely rustic. It had everything we needed including a beautiful view, and peaceful atmosphere. Plenty of firewood and the necessities for those who enjoy simplicity. The shower is quite small for tall people and hot water spare but served its purpose. We took advantage of the kayaks that...
Cozy Cabin on the Canal w Kayaks, Jacuzzi and dock!
Don't see what you're looking for?
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

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Property grounds
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
10.0 out of 10, Exceptional, (7)
"We liked the house, it fit our needs for our plans in Erie. The sunset views over the lake were spectacular. Very clean, Julie was a fast with email replies and communication. The gas fireplace on Friday night was nice while overlooking the lake in the evening. Breakfast was easy in the kitchen both mornings, it had everything we needed for the 3 of us. Well thought out layout and a lot of attention to details. My daughter loved soaking in the huge bathtub Saturday night. Sitting on the front...
The price is HK$1,617
HK$2,369 total
includes taxes & fees
28 Jul - 29 Jul
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)
"Just lovely & clean property. One of the nicest I've stayed in over the last few years. Super comfortable. Coffee station on each floor featuring Starbucks coffee, was a nice touch. Lake frontage of the entire resort was a plus. I recommend this place to anyone. Nice little pool, outdoor carousel bar on harbor front, generously sized rooms. Enjoyed."
The price is HK$1,985
HK$2,243 total
includes taxes & fees
14 Jul - 15 Jul
Chautauqua Harbor Hotel - Jamestown
Quality Inn
Exterior
Quality Inn
2.5 star property
7.6 out of 10, Good, (345)
"Cleanliness, comfort and breakfast option"
The price is HK$1,043
HK$1,179 total
includes taxes & fees
30 Jun - 1 Jul
Quality 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.

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

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?

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!: This holiday home rental outside of Portland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.

Recent reviews of Portland properties
Expedia verified reviews

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

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

5/5 Excellent
Location and great hosts!
"Everything about our stay, the property a the hosts wa amazing. It’s location with the water front location nd walking distance to everything in Bemus Point! Highly recommend!"
A verified traveller stayed at Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Posted 4 days ago
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!