Portland Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Portland holiday rentals

Interior

Cottage in Portland

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
10.0 out of 10, Exceptional, (52 reviews)
"So cute and quaint perfect for our girls weekend !"
United States
Erica W.
The price is HK$1,442
HK$2,617 total
includes taxes & fees
28 Jan - 29 Jan
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Fridge, microwave, oven, stovetop

Holiday Home in findley lake

Step back in time farm house
9.8 out of 10, Exceptional, (77 reviews)
"Charming place!"
United States
Kelly G.
The price is HK$568
HK$1,171 total
includes taxes & fees
28 Jan - 29 Jan
Step back in time farm house
Terrace/patio

Holiday Home in Chautauqua Lake

Lakefront Near Snowmobile Trl-Amazing View-Pets Ok
9.8 out of 10, Exceptional, (13 reviews)
"Great location,nice property with a great living space. Had a wonderful visit. Everything as advertised "
United States
Richard C.
The price is HK$860
HK$1,852 total
includes taxes & fees
27 Jan - 28 Jan
Lakefront Near Snowmobile Trl-Amazing View-Pets Ok
Property grounds

Camping in Forestville

Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
8.0 out of 10, Very good, (1 review)
The price is HK$468
HK$837 total
includes taxes & fees
31 Jan - 1 Feb
Comfortable Camper a few miles off thruway and area attractions. Fire ring wood
Smart TV, fireplace, DVD player

Holiday Home in Dewittville

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
9.8 out of 10, Exceptional, (59 reviews)
"We had a wonderful relaxing time. The house was nice and homey. Will be back next time we visit Lily Dale. "
United States
Anonymous traveller
The price is HK$1,092
HK$2,405 total
includes taxes & fees
27 Jan - 28 Jan
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Fridge, microwave, oven, stovetop

Apartment in Westfield

Beautiful Wine Trail 2-BR Rental
10.0 out of 10, Exceptional, (8 reviews)
"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 HK$1,287
HK$2,370 total
includes taxes & fees
1 Feb - 2 Feb
Beautiful Wine Trail 2-BR Rental
Smart TV, books

Holiday Home in Westfield

Cozy Colonial in Downtown Westfield, NY
10.0 out of 10, Exceptional, (24 reviews)
"Clean and cozy house that was perfect for my family of six. Host was easy to work with and communicated information clearly and promptly. Everything exceeded our expectations. We would definitely stay here again!"
United States
Carrie R.
The price is HK$1,403
HK$2,573 total
includes taxes & fees
27 Jan - 28 Jan
Cozy Colonial in Downtown Westfield, NY
Smart TV, DVD player, books, video library

Holiday Home in Dunkirk

Walk out the door, walk onto the beach!
10.0 out of 10, Exceptional, (78 reviews)
"The house was very clean and agreat location for our visit with family "
United States
Ray K.
The price is HK$1,396
HK$2,291 total
includes taxes & fees
2 Feb - 3 Feb
Walk out the door, walk onto the beach!
Smart TV, fireplace, books

Holiday Home in Celoron

The Refined Retreat
10.0 out of 10, Exceptional, (14 reviews)
"Very nice stay. Well worth it. Cindy is a great host. "
United States
Grace O.
The price is HK$851
HK$2,345 total
includes taxes & fees
27 Jan - 28 Jan
The Refined Retreat
Private kitchen

Apartment in Ripley

3- Bedroom Apartment at an Award Winning Winery
10.0 out of 10, Exceptional, (21 reviews)
"very nice accommodations and close to North East where other family and friends live."
United States
Pamela N.
The price is HK$1,333
HK$2,731 total
includes taxes & fees
27 Jan - 28 Jan
3- Bedroom Apartment at an Award Winning Winery
Smart TV

Apartment in Ripley

3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
9.6 out of 10, Exceptional, (33 reviews)
"Beautiful location!"
United States
Cheri S.
The price is HK$1,298
HK$2,595 total
includes taxes & fees
27 Jan - 28 Jan
3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery
Outdoor dining

Holiday Home in Bemus Point

Charming Resort in the Heart of Bemus Village on CHQ Lake
10.0 out of 10, Exceptional, (198 reviews)
"The family had a great weekend at the Resort on Main!! Great location in town and just minutes from a drive in the country to enjoy the beautiful colors of Fall Hope to visit again!!"
United States
Josiah S.
The price is HK$1,684
HK$3,938 total
includes taxes & fees
27 Jan - 28 Jan
Charming Resort in the Heart of Bemus Village on CHQ Lake
Exterior

Holiday Home in Chautauqua

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
10.0 out of 10, Exceptional, (5 reviews)
"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 HK$1,194
HK$3,058 total
includes taxes & fees
1 Feb - 2 Feb
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Exterior

Holiday Home in Westfield

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
10.0 out of 10, Exceptional, (24 reviews)
"Great property!"
United States
Paul M.
The price is HK$1,945
HK$5,026 total
includes taxes & fees
28 Jan - 29 Jan
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Exterior

Holiday Home in Mayville

Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
9.8 out of 10, Exceptional, (25 reviews)
"We have amazing family time!!! This house has everything to have fun with the kids!!"
United States
Maria Magdalena Q.
The price is HK$1,789
HK$3,819 total
includes taxes & fees
1 Feb - 2 Feb
Four bedroom/three bath. Ideal Winter getaway. Snowmobile trail access.
Exterior

Holiday Home in Ellery

Bemus-HOT TUB-Near Snowmobile Trl-1 Block to Lake
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house, decorated nicely, great accommodations with special touches that made the stay so nice!"
United States
Deanna L.
The price is HK$1,533
HK$3,793 total
includes taxes & fees
27 Jan - 28 Jan
Bemus-HOT TUB-Near Snowmobile Trl-1 Block to Lake
Exterior

Holiday Home in Fredonia

DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms
10.0 out of 10, Exceptional, (4 reviews)
"16 acres of fun and privacy. Nice picnic grounds."
United States
David M.
The price is HK$1,754
HK$2,238 total
includes taxes & fees
27 Jan - 28 Jan
DAY RENTAL ONLY/Picnic Rental -private location, pavilion,pool, restrooms
TV

Apartment in Mayville

Cozy Loft-Pet Friendly-Spacious
The price is HK$729
HK$1,679 total
includes taxes & fees
27 Jan - 28 Jan
Cozy Loft-Pet Friendly-Spacious
Interior

Holiday Home in North East

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
9.6 out of 10, Exceptional, (22 reviews)
"Had a wonderful stay. Owners went out of their way to help us. "
United States
Angela G.
The price is HK$1,488
HK$5,007 total
includes taxes & fees
2 Feb - 3 Feb
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Terrace/patio

Holiday Home in North East

Fall Fun on the Lake - 180 degree Views
10.0 out of 10, Exceptional, (5 reviews)
"House was an amazing place to stay everything was clean and we even got some fish."
United States
Cooper R.
The price is HK$3,470
HK$6,697 total
includes taxes & fees
27 Jan - 28 Jan
Fall Fun on the Lake - 180 degree Views
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

Best Western Dunkirk & Fredonia Inn

Best Western Dunkirk & Fredonia Inn

10/10 Excellent
"Nicole at front desk was wonderful, personable and accommodating. "
Sean 1-night trip
Posted 6 days ago
Best Western Dunkirk & Fredonia Inn

Find out more about Portland

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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 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.