A river with a city skyline in the background, a bridge, and autumn leaves on a tree.

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 house with a brick facade, a chimney, and a front yard with various plants and a tree.

1. Exquisite Historic Suite Close to Downtown 14-21673

Exquisite Historic Suite Close to Downtown 14-21673
Southwest Portland
10.0 out of 10, Exceptional, (559 reviews)
"Place was great!"
United States
Justin T.
The price is AU$207
includes taxes & fees
3 Nov - 4 Nov
Exquisite Historic Suite Close to Downtown 14-21673
A playground with a slide, climbing structures, and a swing set.

2. Guest Suite with WiFi, AC, streaming

Guest Suite with WiFi, AC, streaming
Southwest Portland
9.0 out of 10, Wonderful, (22 reviews)
"This was a very handy place for my Portland visit with nearby services and a trail along the River you could run or walk on for many miles."
United States
Jim M.
The price is AU$373
includes taxes & fees
26 Oct - 27 Oct
Guest Suite with WiFi, AC, streaming
A two-story house with a covered porch and a garden.

3. Pet friendly apartment with covered patio and fenced-in yard.

Pet friendly apartment with covered patio and fenced-in yard.
Southeast Portland
9.8 out of 10, Exceptional, (357 reviews)
"Great stay"
United States
Jack M.
The price is AU$281
includes taxes & fees
1 Nov - 2 Nov
Pet friendly apartment with covered patio and fenced-in yard.
A modern kitchen with black cabinets, a stainless steel refrigerator, and a built-in oven.

4. #StayinMyDistrict Buckman Open Loft-Style Townhome

#StayinMyDistrict Buckman Open Loft-Style Townhome
Southeast Portland
9.8 out of 10, Exceptional, (37 reviews)
"A wonderful spot to stay!"
United States
Edward C.
The price is AU$491
includes taxes & fees
26 Oct - 27 Oct
#StayinMyDistrict Buckman Open Loft-Style Townhome
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area in the background.

5. The Laid-Back Loft | Mississippi Ave

The Laid-Back Loft | Mississippi Ave
North Portland
The price is AU$376
includes taxes & fees
1 Nov - 2 Nov
The Laid-Back Loft | Mississippi Ave
A modern interior with a wooden ceiling, a kitchen area, and a seating area with a colorful rug.

6. #StayInMyDistrict Buckman Spacious Modern Rowhouse

#StayInMyDistrict Buckman Spacious Modern Rowhouse
Southeast Portland
9.6 out of 10, Exceptional, (18 reviews)
"Perfect location and surprisingly quiet."
United States
Paul J.
The price is AU$441
includes taxes & fees
1 Nov - 2 Nov
#StayInMyDistrict Buckman Spacious Modern Rowhouse
A bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

7. #StayinMyDistrict Pendelton Place Walk to Mt Tabor

#StayinMyDistrict Pendelton Place Walk to Mt Tabor
Southeast Portland
8.4 out of 10, Very good, (21 reviews)
"Great spot a few blocks away from Foster Powell. "
United States
Jack
The price is AU$341
includes taxes & fees
26 Oct - 27 Oct
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
A dining area with a wooden table and chairs, a fireplace, and a sofa in the background.

8. #StayInMyDistrict Arbor Lodge The Ainsworth

#StayInMyDistrict Arbor Lodge The Ainsworth
North Portland
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful, welcoming property! Clean, well stocked and with all the necessary amenities. Would highly recommend!!"
United States
David and Sheila R.
The price is AU$481
includes taxes & fees
25 Oct - 26 Oct
#StayInMyDistrict Arbor Lodge The Ainsworth
A modern living room with a large gray sectional sofa, a flat-screen TV mounted on the wall, and a wooden coffee table.

9. Suburban Studio, Near Golf, Wineries & Dining

Suburban Studio, Near Golf, Wineries & Dining
Garden Home-Whitford
The price is AU$405
includes taxes & fees
28 Oct - 29 Oct
Suburban Studio, Near Golf, Wineries & Dining
A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

10. Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!

Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
Southeast Portland
9.8 out of 10, Exceptional, (12 reviews)
"This is an amazing location. Walkability is excellent and the property is so quaint. We would love to stay here again. "
United States
Arlene L.
Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

11. Granny Flat in leafy SW Portland

Granny Flat in leafy SW Portland
Southwest Portland
9.6 out of 10, Exceptional, (31 reviews)
"Literally enjoyed the place, the host were extremely good at communicating and very understanding. Definitely a 9.5/10"
United States
Daquarious
The price is AU$208
includes taxes & fees
22 Oct - 23 Oct
Granny Flat in leafy SW Portland
A living room with a brown leather sofa, a striped armchair, a white coffee table, a flat-screen TV mounted on the wall, and a window with an umbrella outside.

12. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Great location near Sellwood shops & tea, bakery & restaurants."
United States
dan v.
The price is AU$354
includes taxes & fees
27 Oct - 28 Oct
#StayinMyDistrict Sellwood Coco Rose Retreat
A modern kitchen with a large island, white cabinetry, and a flat-screen TV mounted above the counter.

13. Cozy Private Cottage Near Downtown Portland

Cozy Private Cottage Near Downtown Portland
Northeast Portland
10.0 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay. Convenient location. Owners were very responsive to messages. Would definitely stay here again!"
United States
Juliette L.
The price is AU$395
includes taxes & fees
23 Oct - 24 Oct
Cozy Private Cottage Near Downtown Portland
A modern living room with a sectional sofa, a coffee table, a flat-screen TV, and a fireplace.

14. Most Family Friendly Listing in Portland - Keep the Conveniences of Home!

Most Family Friendly Listing in Portland - Keep the Conveniences of Home!
Southwest Portland
9.8 out of 10, Exceptional, (59 reviews)
"The rental was exactly what we needed. It had plenty of space, the beds were comfortable, the kitchen was well stocked, it was clean. It was in a great area. Would definitely stay again."
United States
Tracy M.
The price is AU$400
includes taxes & fees
3 Nov - 4 Nov
Most Family Friendly Listing in Portland - Keep the Conveniences of Home!
A patio with outdoor furniture, a clock, and a wooden fence.

15. Bungalow Guest House

Bungalow Guest House
Ellsworth
8.8 out of 10, Excellent, (41 reviews)
"Rosie was a grand host and made us feel very welcome."
United States
TeriLee H.
The price is AU$308
includes taxes & fees
26 Oct - 27 Oct
Bungalow Guest House
A wooden cabin with a front porch, a staircase, and a garden.

16. Hip and cozy dog-friendly Mississippi Victorian

Hip and cozy dog-friendly Mississippi Victorian
North Portland
10.0 out of 10, Exceptional, (17 reviews)
"Great location"
United States
Ivy S.
The price is AU$467
includes taxes & fees
10 Nov - 11 Nov
Hip and cozy dog-friendly Mississippi Victorian
A rustic outdoor seating area with benches and picnic tables, surrounded by dense forest.

17. Creekside Haven

Creekside Haven
Wilsonville
10.0 out of 10, Exceptional, (76 reviews)
"Very comfortable ,had everything we needed. Wish we could have stayed longer."
United States
Eric S.
The price is AU$326
includes taxes & fees
27 Oct - 28 Oct
Creekside Haven
A compact kitchen with a sink, stove, and dining area.

18. Tiny Farmhouse - Walk to Local Shops & Restaurants

Tiny Farmhouse - Walk to Local Shops & Restaurants
Southeast Portland
10.0 out of 10, Exceptional, (4 reviews)
"Space was great for our 1 night stay!"
United States
Kelsey C.
The price is AU$335
includes taxes & fees
28 Oct - 29 Oct
Tiny Farmhouse - Walk to Local Shops & Restaurants
A living room with a coffee table, books, a lamp, a potted plant, and a framed picture on the wall.

19. Two Rivers Relaxing Retreat

Two Rivers Relaxing Retreat
Northeast Portland
9.8 out of 10, Exceptional, (70 reviews)
"Very nice place. Beautiful garden, peaceful neighborhood, comfortable bed."
United States
Kelly W.
The price is AU$351
includes taxes & fees
3 Nov - 4 Nov
Two Rivers Relaxing Retreat
A modern kitchen with white cabinets, a built-in oven, and a coffee maker.

20. #StayinMyDistrict Kenton Private Guest House

#StayinMyDistrict Kenton Private Guest House
North Portland
8.6 out of 10, Excellent, (13 reviews)
"The house is perfectly functional for 2 people. It was very clean and well organized! We appreciated having coffee there for the first morning and ice in the freezer! The bed was very comfortable. The house was easy to find."
United States
Marla T.
The price is AU$309
includes taxes & fees
22 Oct - 23 Oct
#StayinMyDistrict Kenton Private Guest House
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

The Royal Sonesta Portland Downtown

The Royal Sonesta Portland Downtown

10/10 Excellent
"Rooms were very clean and unique. Staff were very friendly"
Tara 2-night trip
Posted 4 hours ago
The Royal Sonesta Portland Downtown

Find out more about Portland

Portland Holiday Homes information

Number of reviews
1,210
Accommodation
717 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$491

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