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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (4 reviews)
"Great little place. We loved our short stay."
United States
Julie P.
The price is €181
includes taxes & fees
27 Oct - 28 Oct
Lake Erie Retreat
A two-story house with a deck, a barbecue grill, and a sofa.

2. 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, (19 reviews)
"Beautiful views of the lake and a nice little place to stay!"
United States
Kierstyn I.
The price is €235
includes taxes & fees
26 Oct - 27 Oct
Lakefront w Dock-Pets OK-Amazing Views-Large Deck
Rear hall with bathroom and bedroom entrance.

3. 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 €209
includes taxes & fees
26 Oct - 27 Oct
The Stable at Windmill Ridge Farm
Room

4. Spacious 3BR Home with Pool Table & Patio Near Lake Erie

Spacious 3BR Home with Pool Table & Patio Near Lake Erie
Westfield
The price is €286
includes taxes & fees
2 Nov - 3 Nov
Spacious 3BR Home with Pool Table & Patio Near Lake Erie
A laundry room with a white washing machine and dryer, a white cabinet with drawers, and a floral-patterned wall.

5. Stay on Main: Stylish loft in heart of the village

Stay on Main: Stylish loft in heart of the village
Westfield
The price is €223
includes taxes & fees
5 Nov - 6 Nov
Stay on Main: Stylish loft in heart of the village
A two-story building with a front door and windows, surrounded by gravel and greenery.

6. Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (32 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 €310
includes taxes & fees
5 Nov - 6 Nov
Cozy Colonial in Downtown Westfield, NY
A living room with a stone fireplace, a television, and a dining area in the background.

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

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (99 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
The price is €283
includes taxes & fees
26 Oct - 27 Oct
Walk out the door, walk onto the beach!
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.
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A kitchen with a central island, bar stools, a hanging light fixture, and a painting on the wall.

9. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (102 reviews)
"Our second stay at this property, awesome we will be back"
United States
Harry C.
The price is €138
includes taxes & fees
2 Nov - 3 Nov
Step back in time farm house
Lakefront dining table with seating for 8 around the table

10. Casa Andante - Lakefront Escape

Casa Andante - Lakefront Escape
Mayville
10.0 out of 10, Exceptional, (70 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.
Casa Andante - Lakefront Escape
A house with a porch, a small garden with flowers, and a starry night sky.

11. Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.

Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.
Mayville
10.0 out of 10, Exceptional, (42 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 €488
includes taxes & fees
25 Oct - 26 Oct
Fall colors, cozy firepits, and perfect family gathering times await on 5 Acres.
A campfire with four Adirondack chairs around it, set in a forested area with a picnic table in the background.

12. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful location! We enjoyed the peaceful quiet time."
United States
Anonymous traveller
The price is €295
includes taxes & fees
25 Oct - 26 Oct
Quiet Escape, Peaceful Lake Glimpses
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.

13. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (27 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is €327
includes taxes & fees
5 Nov - 6 Nov
The Refined Retreat
A lakeside patio with outdoor seating, a dock, and boats.

14. Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake
Bemus Point
10.0 out of 10, Exceptional, (226 reviews)
"A beautiful hotel in a great location."
United States
Elizabeth N.
The price is €453
includes taxes & fees
27 Oct - 28 Oct
Charming Resort in the Heart of Bemus Village on CHQ Lake
An outdoor seating area with tables and chairs, overlooking a body of water with boats and a sunset in the background.

15. 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, (38 reviews)
"Perfect location in Bemus Point. Walking distance to everything! Highly recommend!"
United States
Chris S.
The price is €486
includes taxes & fees
3 Nov - 4 Nov
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
A landscaped garden with a pathway leading to a building with a green roof.

16. Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
Bemus Point
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay!"
United States
RupczykNC U.
The price is €420
includes taxes & fees
5 Nov - 6 Nov
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
A two-story house with a front porch, a well-maintained lawn, and a large flowering shrub.

17. 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, (13 reviews)
"Love the property. Will definitely stay there again. "
United States
Melissa J.
The price is €427
includes taxes & fees
26 Oct - 27 Oct
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
A modern kitchen with a central island, pendant lighting, and a view into the dining area.

18. 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 €720
includes taxes & fees
25 Oct - 26 Oct
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.

19. 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, (108 reviews)
"The view of Lake Erie was beautiful from the house. The house had everything my family needed and it was very clean. I also was happy to know it welcomed pets my dog really enjoyed exploring the grounds. My grandkids enjoyed making a fire every night and we appreciate the fire wood they left for us to use."
United States
Charles T.
The price is €548
includes taxes & fees
28 Oct - 29 Oct
Big Beach Fantastic Lakeview Private Lake and Beach Access Close to Wineries
An outdoor patio with a fire pit, seating, and a view of a lake.

20. Stunning Lakefront Cottage with Panoramic Lake Views & Unforgettable Sunsets

Stunning Lakefront Cottage with Panoramic Lake Views & Unforgettable Sunsets
Jamestown
The price is €420
includes taxes & fees
25 Oct - 26 Oct
Stunning Lakefront Cottage with Panoramic Lake Views & Unforgettable Sunsets
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

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

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

10/10 Excellent
"Beautiful location. Charming, cozy, lovely home. Perfectly decorated. Immaculate. Everything we could want was already there. Well stocked kitchen. Lots of firewood, clean & well cut. Communication with host was easy with immediate response. Instructions were clear. We will be going back!"
Laureen S. 2-night trip
Posted 9 hours ago
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Find out more about Portland

Portland Holiday Homes information

Number of reviews
844
Accommodation
165 Holiday Homes
Lowest Price
€138
Highest Price
€720