Portland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Portland vacation rentals

Terrace/patio
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Portland
10.0 out of 10, Exceptional, (51)
"The stay made for a wonderful girls weekend!"
United States
Christine W.
The price is ￥28,812
￥52,268 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Property grounds
Small camper in the country

Small camper in the country

Small camper in the country
Dewittville
9.8 out of 10, Exceptional, (19)
"Had a great time, unfortunately it rained the entire time we were there but the Rv was very clean and the host was amazing. We will definitely come visit again."
United States
Ashley M.
The price is ￥9,344
￥14,078 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Small camper in the country
Outdoor dining
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
1.0 star property
Forestville
8.0 out of 10, Very Good, (1)
The price is ￥9,344
￥16,718 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
Fridge, microwave, oven, stovetop
Peaceful, Serene, Lake View thru the trees

Peaceful, Serene, Lake View thru the trees

Peaceful, Serene, Lake View thru the trees
2.0 star property
Ashville
10.0 out of 10, Exceptional, (16)
"It was a calm safe space when we needed one. "
United States
Teresa C.
The price is ￥14,114
￥43,061 total
includes taxes & fees
Dec 16 - Dec 17
Peaceful, Serene, Lake View thru the trees
Smart TV, fireplace, books
The Refined Retreat

The Refined Retreat

The Refined Retreat
Celoron
10.0 out of 10, Exceptional, (13)
"Very clean and organized. Easy in and out. "
United States
scott r.
The price is ￥17,007
￥46,672 total
includes taxes & fees
Dec 14 - Dec 15
The Refined Retreat
Fridge, microwave, oven, stovetop
Step back in time farm house

Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (75)
"Great place to stay! Enjoyed the decor and location."
United States
Thomas B.
The price is ￥11,355
￥23,392 total
includes taxes & fees
Dec 15 - Dec 16
Step back in time farm house
Terrace/patio
Lakefront w Dock, Pet Friendly, Spacious Yard

Lakefront w Dock, Pet Friendly, Spacious Yard

Lakefront w Dock, Pet Friendly, Spacious Yard
2.0 star property
Chautauqua Lake
9.8 out of 10, Exceptional, (13)
"This was a great property to stay at! I couldn’t have asked for anything different. What stood out the most was how clean everything was and how friendly the host was; all our questions were answered promptly and the host was exceedingly helpful. Overall great place to stay!"
United States
Melissa C.
The price is ￥18,642
￥37,962 total
includes taxes & fees
Dec 12 - Dec 13
Lakefront w Dock, Pet Friendly, Spacious Yard
Interior
Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (78)
"The house was very clean and agreat location for our visit with family "
United States
Ray K.
The price is ￥30,992
￥72,682 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Walk out the door, walk onto the beach!
Fridge, microwave, oven, stovetop
Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
10.0 out of 10, Exceptional, (8)
"Very clean, very well appointed and the owners were very accommodating Easy parking and close to all the areas we wanted to go toI would stay there again"
United States
harry w.
The price is ￥25,697
￥47,868 total
includes taxes & fees
Dec 20 - Dec 21
Beautiful Wine Trail 2-BR Rental
Interior
The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm
Fredonia
9.6 out of 10, Exceptional, (14)
"I enjoyed this little "house", Very clean!! "
United States
Marvin M.
The price is ￥15,574
￥32,557 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Stable at Windmill Ridge Farm
Exterior
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Westfield
10.0 out of 10, Exceptional, (23)
"Our stay was wonderful! The house was amazing and the host even better."
United Kingdom
Ashley C.
The price is ￥42,534
￥100,332 total
includes taxes & fees
Dec 14 - Dec 15
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Smart TV, books
Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (24)
"Great property in the perfect location. Very clean, updated property. We will definitely stay again. "
United States
Marci S.
The price is ￥30,837
￥54,908 total
includes taxes & fees
Dec 12 - Dec 13
Cozy Colonial in Downtown Westfield, NY
Fridge, microwave, oven, stovetop
Main St Bemus-HOT TUB-1 Block from Lake

Main St Bemus-HOT TUB-1 Block from Lake

Main St Bemus-HOT TUB-1 Block from Lake
Ellery
10.0 out of 10, Exceptional, (7)
"This property is an absolute gem! Our young family has stayed in quite a few rental properties in the past, and this one has been the most enjoyable by far. So much to do for the little ones, ample and flexible sleeping arrangements, and the attention to the little things (like the super soft hot tub towels and the s’mores supplies) were the icing on top. Highly recommend this place, and we hope to be back at our next family reunion! "
United States
Alyssa P.
The price is ￥33,115
￥78,952 total
includes taxes & fees
Dec 12 - Dec 13
Main St Bemus-HOT TUB-1 Block from Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (2)
"It was a very clean house with spacious areas including a full apartment upstairs. It was one of the better places we have ever stayed at as far as accommodations go. Highly recommended! Thank you."
United Kingdom
Bill T.
The price is ￥25,168
￥62,405 total
includes taxes & fees
Dec 12 - Dec 13
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Microwave, oven, stovetop, dishwasher
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Ripley
9.6 out of 10, Exceptional, (33)
"Beautiful location!"
United States
Cheri S.
The price is ￥25,931
￥51,829 total
includes taxes & fees
Dec 20 - Dec 21
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Property grounds
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Dewittville
9.8 out of 10, Exceptional, (59)
"We had a wonderful relaxing time. The house was nice and homey. Will be back next time we visit Lily Dale. "
United States
Anonymous traveler
The price is ￥21,804
￥47,869 total
includes taxes & fees
Dec 12 - Dec 13
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Private kitchen
3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery

3- Bedroom Apartment at an Award Winning Winery
2.0 star property
Ripley
10.0 out of 10, Exceptional, (21)
"very nice accommodations and close to North East where other family and friends live."
United States
Pamela N.
The price is ￥26,632
￥54,556 total
includes taxes & fees
Dec 12 - Dec 13
3- Bedroom Apartment at an Award Winning Winery
Interior
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

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

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
North East
9.6 out of 10, Exceptional, (21)
"Had a wonderful stay. Owners went out of their way to help us. "
United States
Angela G.
The price is ￥29,498
￥100,070 total
includes taxes & fees
Dec 15 - Dec 16
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Exterior
Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.

Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.

Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
Mayville
9.8 out of 10, Exceptional, (23)
"We have amazing family time!!! This house has everything to have fun with the kids!!"
United States
Maria Magdalena Q.
The price is ￥32,939
￥62,740 total
includes taxes & fees
Dec 15 - Dec 16
Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
Marina
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

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

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Bemus Point
10.0 out of 10, Exceptional, (118)
"Like home away from home Basics there just bring u food n enjoy!"
United States
Kathy S.
The price is ￥42,829
￥90,457 total
includes taxes & fees
Dec 29 - Dec 30
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
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

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent
"Beautiful room, wonderful staff, excellent food and service. "
Robert 1-night trip
Posted 3 days ago
Chautauqua Harbor Hotel - Jamestown

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 vacation rental in Portland?

Yes, there are vacation rentals close to popular attractions in Portland, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Portland has to offer?

Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!: This vacation home rental outside of Portland is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation 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 larger area, you’ll find 21 Brix Winery and Lily Dale Spiritual Center.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can reserve for a couple days or more in Portland. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.