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Holiday Homes in Portland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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, (557 reviews)
"A wonderful stay in Portland. A beautiful place, very clean and comfortable and a friendly and welcoming host. Would 100% recommend."
United Kingdom
Celine
The price is €132
includes taxes & fees
9 Nov - 10 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)
"Space was actually much larger than I thought it would be, very clean. I was worried when I saw street parking, but it was absolutely no issue at all- located in a quiet neighborhood with lots of restaurants/cafes in walkable distance."
United States
Madison
The price is €236
includes taxes & fees
19 Oct - 20 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 €178
includes taxes & fees
19 Oct - 20 Oct
Pet friendly apartment with covered patio and fenced-in yard.
Property grounds

4. #StayInMyDistrict Overlook Backyard Tiny Suite

#StayInMyDistrict Overlook Backyard Tiny Suite
North Portland
8.0 out of 10, Very good, (5 reviews)
"This is definitely a small space. If you want a cozy bed, clean shower and a hot cup of coffee, this is definitely for you!!There is a cute park down the street where you can catch an amazing sunset!"
United States
Nikki D.
The price is €196
includes taxes & fees
19 Oct - 20 Oct
#StayInMyDistrict Overlook Backyard Tiny Suite
A modern kitchen with black cabinets, a stainless steel refrigerator, and a built-in oven.

5. #StayinMyDistrict Buckman Open Loft-Style Townhome

#StayinMyDistrict Buckman Open Loft-Style Townhome
Southeast Portland
9.8 out of 10, Exceptional, (37 reviews)
"Place was perfect for my one night stopover, but would also work for multiple nights. Great location."
United States
Brian O.
#StayinMyDistrict Buckman Open Loft-Style Townhome
A blue house with a white porch and a pathway leading to it.

6. Charming 2-bedroom in historic home

Charming 2-bedroom in historic home
Southeast Portland
9.6 out of 10, Exceptional, (48 reviews)
"Very walkable location. Love the private entrance and the space suited just perfectly. "
United States
Jamie A.
The price is €202
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom in historic home
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

7. 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 €132
includes taxes & fees
19 Oct - 20 Oct
Granny Flat in leafy SW Portland
A modern living room with a dining area, large windows, and a fireplace.

8. ❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO

❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
Northeast Portland
10.0 out of 10, Exceptional, (58 reviews)
"Close to Starbucks "
United States
J J.
The price is €312
includes taxes & fees
19 Oct - 20 Oct
❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

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

Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
Southeast Portland
10.0 out of 10, Exceptional, (11 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 bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

10. #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 €220
includes taxes & fees
19 Oct - 20 Oct
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
Off-property: Laughing Planet storefront and outdoor tables.

11. Color Splash - Fast WiFi - Heart of Hawthorne

Color Splash - Fast WiFi - Heart of Hawthorne
Southeast Portland
10.0 out of 10, Exceptional, (1 review)
"The apartment was very cute and clean and the location is fantastic. The host was super responsive and helpful. A few minor things to note in case they matter to you: the mattress is very soft; the microwave is on a shelf above the refrigerator - there’s a step stool but it can be tricky for things like soup; there’s very little counter space in the kitchen. Other than that the living room is spacious, the couch is full size and very comfortable for watching tv, and the bedroom is light and...
United States
Michelle S.
Color Splash - Fast WiFi - Heart of Hawthorne
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area in the background.

12. The Laid-Back Loft | Mississippi Ave

The Laid-Back Loft | Mississippi Ave
North Portland
The price is €260
includes taxes & fees
19 Oct - 20 Oct
The Laid-Back Loft | Mississippi Ave
A modern interior with a wooden ceiling, a kitchen area, and a seating area with a colorful rug.

13. #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 €267
includes taxes & fees
19 Oct - 20 Oct
#StayInMyDistrict Buckman Spacious Modern Rowhouse
A compact, modern room with a wooden ceiling, a bed with pillows, a small kitchen area with a sink, and a dining table with chairs.

14. The Sunstone • Modern Tiny House • Prime Location

The Sunstone • Modern Tiny House • Prime Location
Southeast Portland
8.0 out of 10, Very good, (5 reviews)
"My second stay. It is a wonderful and quiet respite after spending full days with family. Air conditioning was a plus during the heat spell."
United States
Margaret W.
The price is €192
includes taxes & fees
21 Oct - 22 Oct
The Sunstone • Modern Tiny House • Prime Location
A living room with a fireplace, a television, and a bookshelf.

15. Book NOW for Summer Fun! - Perfect for family! - Fully Loaded! - Fire Pit!

Book NOW for Summer Fun! - Perfect for family! - Fully Loaded! - Fire Pit!
Bethany
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Location and priced properly. "
United States
David P.
The price is €451
includes taxes & fees
17 Oct - 18 Oct
Book NOW for Summer Fun! - Perfect for family! - Fully Loaded! - Fire Pit!
A dining area with a wooden table and chairs, a fireplace, and a sofa in the background.

16. #StayInMyDistrict Arbor Lodge The Ainsworth

#StayInMyDistrict Arbor Lodge The Ainsworth
North Portland
9.2 out of 10, Wonderful, (15 reviews)
"This house and location could not have been more perfect for our family of 4 (two teenage boys). The beds are comfy and the neighborhood is great. We were within 10 minutes of the zoo, downtown and all that Portland has to offer. The host is incredibly responsive and I would definitely stay here again. Also, the Alberta Arts district is super close and has so many good spots."
United States
amiee k.
The price is €323
includes taxes & fees
19 Oct - 20 Oct
#StayInMyDistrict Arbor Lodge The Ainsworth
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.

17. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Very clean, well equipted , great location, comfortable bed, great spot for coffee outside"
United States
Sorek Y.
#StayinMyDistrict Sellwood Coco Rose Retreat
A rustic outdoor seating area with benches and picnic tables, surrounded by dense forest.

18. Creekside Haven

Creekside Haven
Wilsonville
10.0 out of 10, Exceptional, (75 reviews)
"Very comfortable ,had everything we needed. Wish we could have stayed longer."
United States
Eric S.
The price is €211
includes taxes & fees
15 Oct - 16 Oct
Creekside Haven
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, (68 reviews)
"Nice space in a great location!"
United States
Emily L.
Two Rivers Relaxing Retreat
A modern kitchen with a large island, white cabinetry, and a flat-screen TV mounted above the counter.

20. Cozy Private Cottage Near Downtown Portland

Cozy Private Cottage Near Downtown Portland
Northeast Portland
10.0 out of 10, Exceptional, (70 reviews)
Cozy Private Cottage Near Downtown Portland
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

Eastside Lodge

Eastside Lodge

8/10 Good
"The shower was aimed towards the wall."
Sarah 3-night trip
Posted less than an hour ago
Eastside Lodge

Find out more about Portland

Portland Holiday Homes information

Number of reviews
1,363
Accommodation
727 Holiday Homes
Lowest Price
€132
Highest Price
€451