Portland Vacation Homes

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

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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

Southwest Portland

Celine

HK$1,124 total

includes taxes & fees

9 Nov - 10 Nov

A playground with a slide, climbing structures, and a swing set.

2. Guest Suite with WiFi, AC, streaming

Southwest Portland

Madison

HK$2,028 total

includes taxes & fees

18 Oct - 19 Oct

A two-story house with a covered porch and a garden.

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

Southeast Portland

Jack M.

HK$1,534 total

includes taxes & fees

19 Oct - 20 Oct

4. #StayInMyDistrict Overlook Backyard Tiny Suite

North Portland

Nikki D.

HK$1,771 total

includes taxes & fees

19 Oct - 20 Oct

A modern interior with a wooden ceiling, a kitchen area, and a seating area with a colorful rug.

5. #StayInMyDistrict Buckman Spacious Modern Rowhouse

Southeast Portland

Paul J.

HK$2,459 total

includes taxes & fees

19 Oct - 20 Oct

A blue house with a white porch and a pathway leading to it.

6. Charming 2-bedroom in historic home

Southeast Portland

Jamie A.

HK$1,777 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with black cabinets, a stainless steel refrigerator, and a built-in oven.

7. #StayinMyDistrict Buckman Open Loft-Style Townhome

Southeast Portland

Brian O.

HK$2,641 total

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with white cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

8. Granny Flat in leafy SW Portland

Southwest Portland

Daquarious

HK$1,078 total

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a sectional sofa, a coffee table, a flat-screen TV, and a fireplace.

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

Southwest Portland

Tracy M.

HK$2,086 total

includes taxes & fees

21 Oct - 22 Oct

Off-property: Laughing Planet storefront and outdoor tables.

10. Color Splash - Fast WiFi - Heart of Hawthorne

Southeast Portland

"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...

Michelle S.

HK$1,920 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with a large island, white cabinetry, and a flat-screen TV mounted above the counter.

11. Cozy Private Cottage Near Downtown Portland

Northeast Portland

Juliette L.

HK$2,125 total

includes taxes & fees

23 Oct - 24 Oct

A bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

12. #StayinMyDistrict Pendelton Place Walk to Mt Tabor

Southeast Portland

Jack

HK$1,811 total

includes taxes & fees

13 Oct - 14 Oct

A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area in the background.

13. The Laid-Back Loft | Mississippi Ave

North Portland

HK$1,964 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

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

Southeast Portland

Arlene L.

HK$2,043 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a fireplace, a television, and a bookshelf.

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

Bethany

David P.

HK$3,852 total

includes taxes & fees

17 Oct - 18 Oct

A modern living room with a dining area, large windows, and a fireplace.

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

Northeast Portland

J J.

HK$2,790 total

includes taxes & fees

19 Oct - 20 Oct

A wooden cabin with a front porch, a staircase, and a garden.

17. Hip and cozy dog-friendly Mississippi Victorian

North Portland

Ivy S.

HK$2,237 total

includes taxes & fees

13 Oct - 14 Oct

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.

18. The Sunstone • Modern Tiny House • Prime Location

Southeast Portland

Margaret W.

HK$1,635 total

includes taxes & fees

12 Oct - 13 Oct

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

Northeast Portland

Emily L.

HK$1,943 total

includes taxes & fees

14 Oct - 15 Oct

A rustic outdoor seating area with benches and picnic tables, surrounded by dense forest.

20. Creekside Haven

Wilsonville

Eric S.

HK$1,749 total

includes taxes & fees

12 Oct - 13 Oct

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Top Portland Hotel Reviews

Oxford Suites Portland - Jantzen Beach

10/10 Excellent

"Friendly stuff, good location, and the clean environment is why we will be back. We had a great experience :)"

Country Inn & Suites by Radisson, Portland International Airport, OR

10/10 Excellent

"Love the convenience to the airport and that I can leave my vehicle at the hotel. Prices for long term stay could be cheaper, since you already pay yo stay there. It doe need to have the carpets cleaned. I stay here every time I fly and found areas even in my room that needed to be cleaned properly. Otherwise, I will continue to stay."

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