A large suspension bridge with a distinctive gothic arch design, spanning over a forested area.

Holiday Homes in Portland

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Portland holiday homes

A modern living room with a dining table, sofa, and staircase.

1. Lake Erie Retreat

Lake Erie Retreat
Dunkirk
10.0 out of 10, Exceptional, (1 review)
"I was impressed with the cleanseliness and the warm and inviting atmosphere."
United States
Amanda G.
The price is €188
includes taxes & fees
15 Sept - 16 Sept
Lake Erie Retreat
A living room with a stone fireplace, a television, and a dining area in the background.

2. Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
Walk out the door, walk onto the beach!
A modern kitchen with wooden chairs, a dining table, and a black cabinet.

3. Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (31 reviews)
"Great clean place in a good part of town so we were able to walk to the bars and restaurants in a few minutes. Will for sure book this same place next year when we are up on fishing trip and wine arounds."
United States
Ken
The price is €305
includes taxes & fees
3 Sept - 4 Sept
Cozy Colonial in Downtown Westfield, NY

4. The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm
Fredonia
9.6 out of 10, Exceptional, (18 reviews)
"Superb place "
Canada
Jonathan M.
The price is €217
includes taxes & fees
15 Sept - 16 Sept
The Stable at Windmill Ridge Farm
A spacious living area with a dining table, a sofa, and a kitchen with wooden cabinets and a built-in island.

5. 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, (70 reviews)
"We had a great time. Was the perfect home away from home for a couple days."
United States
Juliann G.
The price is €255
includes taxes & fees
1 Oct - 2 Oct
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
A two-story house with a deck, a barbecue grill, and a sofa.

6. Lakefront w Dock-Pets OK-Amazing Views-Large Deck

Lakefront w Dock-Pets OK-Amazing Views-Large Deck
Chautauqua Lake
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful views of the lake and a nice little place to stay!"
United States
Kierstyn I.
The price is €276
includes taxes & fees
21 Sept - 22 Sept
Lakefront w Dock-Pets OK-Amazing Views-Large Deck
A kitchen with white cabinets, a granite countertop, and a ceiling light fixture.

7. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (96 reviews)
"Everything was clean and comfortable. The location was great! We enjoyed our stay."
United States
Leslie E.
The price is €134
includes taxes & fees
3 Sept - 4 Sept
Step back in time farm house
A single-story house with a front porch, a small garden, and a driveway.

8. 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, (8 reviews)
"Great property. Tiffany thought of everything. It was all so welcoming and new. Would definitely stay here again. "
United States
Jennifer L.
The price is €445
includes taxes & fees
3 Sept - 4 Sept
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A campfire with four Adirondack chairs around it, set in a forested area with a picnic table in the background.

9. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful view of the lake. Very nice little house and quiet. "
United States
Joelyn G.
Quiet Escape, Peaceful Lake Glimpses
A stone fire pit surrounded by wooden logs and benches in a grassy area with trees in the background.

10. Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.

Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.
North East
9.6 out of 10, Exceptional, (13 reviews)
"nice quiet place to stay,close to boat launch also"
United States
martin v.
The price is €226
includes taxes & fees
14 Sept - 15 Sept
Relax on 10 acres. Walk to the lake any season: Swim, Fish, Wine, Ski, Relax.
A house with a porch, a small garden with flowers, and a starry night sky.

11. Gorgeous Fall colors await! Perfect for families or groups. Spacious 4BR 3 BTH.

Gorgeous Fall colors await! Perfect for families or groups. Spacious 4BR 3 BTH.
Mayville
10.0 out of 10, Exceptional, (38 reviews)
"The home was clean, host responded to requests promptly. This is our 2nd stay and on the list for next time "
United States
Joseph D.
The price is €493
includes taxes & fees
28 Sept - 29 Sept
Gorgeous Fall colors await! Perfect for families or groups. Spacious 4BR 3 BTH.
A modern living room with a fireplace, a flat-screen TV, a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

12. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (24 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is €300
includes taxes & fees
3 Sept - 4 Sept
The Refined Retreat

13. Casa Andante - Lakefront Escape

Casa Andante - Lakefront Escape
Mayville
10.0 out of 10, Exceptional, (68 reviews)
"Our family celebrated a beautiful weekend at Casa Adante. The property provided everything we needed, easy check in, serene lake views, proximity to cool places around the lake, and plenty of space. Thank you to the hosts for creating a cozy place where amazing memories were made! "
United States
Georgann F.
The price is €927
includes taxes & fees
21 Sept - 22 Sept
Casa Andante - Lakefront Escape
An outdoor seating area with tables and chairs, overlooking a body of water with boats and a sunset in the background.

14. Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
Bemus Point
9.8 out of 10, Exceptional, (37 reviews)
"Bet nice house. Lots of room to spread out plus a nice bonus room upstairs. "
United States
John W.
The price is €501
includes taxes & fees
3 Oct - 4 Oct
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
A modern kitchen with a central island, pendant lighting, and a view into the dining area.

15. Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites

Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
Ashville
10.0 out of 10, Exceptional, (2 reviews)
"This was a beautiful house!! Very clean and had everything we needed and more! The hosts were very helpful and communicated very quickly! I highly recommend staying in this house!"
United States
Janson D.
The price is €554
includes taxes & fees
3 Sept - 4 Sept
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
A wooden deck with benches and a picnic table, a red building with a white door, and trees in the background.

16. Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries

Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries
North East
10.0 out of 10, Exceptional, (107 reviews)
"Great communication. The place was warm and homey. It was a great place to spend our Christmas break. "
United States
Greg L.
The price is €536
includes taxes & fees
16 Sept - 17 Sept
Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries
A bedroom with a large bed, a desk, a chair, and a view of the outdoors through large windows.

17. Treat yourself - Enjoy Fall or Winter on the lake.

Treat yourself - Enjoy Fall or Winter on the lake.
North East
10.0 out of 10, Exceptional, (111 reviews)
"This was the best VRBO we have ever stayed in!!"
United States
Debbie N.
The price is €410
includes taxes & fees
24 Sept - 25 Sept
Treat yourself - Enjoy Fall or Winter on the lake.
A dining area with a table and chairs, large windows, and a view of a snowy landscape.

18. 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
9.8 out of 10, Exceptional, (27 reviews)
"Nice place very roomy. Perfect location for the wedding we attended. "
United States
John H.
The price is €697
includes taxes & fees
15 Sept - 16 Sept
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
A two-story house with a front porch, a well-maintained lawn, and a large flowering shrub.

19. Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake

Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
Ellery
10.0 out of 10, Exceptional, (10 reviews)
"Love the property. Will definitely stay there again. "
United States
Melissa J.
The price is €542
includes taxes & fees
7 Sept - 8 Sept
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
A covered outdoor seating area with two wooden Adirondack chairs, a table with a glass of wine, and a view of the ocean at sunset.

20. Relax on the Lake - 180 degree Views

Relax on the Lake - 180 degree Views
North East
10.0 out of 10, Exceptional, (8 reviews)
"House was an amazing place to stay everything was clean and we even got some fish."
United States
Cooper R.
The price is €739
includes taxes & fees
3 Sept - 4 Sept
Relax 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

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent
"The hotel vastly exceeded expectations in every way. It is truly a 5 star experience. The hotel has massive lakefront and is incredibly well maintained. The service is well above a normal hotel. If I had known how nice it was I would’ve planned a longer stay. I can’t wait to go back"
Christopher 1-night trip
Posted 2 hours ago
Chautauqua Harbor Hotel - Jamestown

Find out more about Portland

Portland Holiday Homes information

Number of reviews
799
Accommodation
170 Holiday Homes
Lowest Price
€134
Highest Price
€927