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Holiday Homes in Portland

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 NZ$276
includes taxes & fees
14 Oct - 15 Oct
Exquisite Historic Suite Close to Downtown 14-21673
A two-story house with a covered porch and a garden.

2. 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, (355 reviews)
"Great stay"
United States
Jack M.
The price is NZ$346
includes taxes & fees
19 Oct - 20 Oct
Pet friendly apartment with covered patio and fenced-in yard.
Property grounds

3. #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 NZ$359
includes taxes & fees
6 Oct - 7 Oct
#StayInMyDistrict Overlook Backyard Tiny Suite
A playground with a slide, climbing structures, and a swing set.

4. 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 NZ$456
includes taxes & fees
6 Oct - 7 Oct
Guest Suite with WiFi, AC, streaming
A modern interior with a wooden ceiling, a kitchen area, and a seating area with a colorful rug.

5. #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 NZ$518
includes taxes & fees
11 Oct - 12 Oct
#StayInMyDistrict Buckman Spacious Modern Rowhouse
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, (47 reviews)
"Very walkable location. Love the private entrance and the space suited just perfectly. "
United States
Jamie A.
The price is NZ$424
includes taxes & fees
8 Oct - 9 Oct
Charming 2-bedroom in historic home
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 NZ$400
includes taxes & fees
6 Oct - 7 Oct
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
A modern kitchen with black cabinets, a stainless steel refrigerator, and a built-in oven.

8. #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.
The price is NZ$609
includes taxes & fees
11 Oct - 12 Oct
#StayinMyDistrict Buckman Open Loft-Style Townhome
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

9. Granny Flat in leafy SW Portland

Granny Flat in leafy SW Portland
Southwest Portland
9.4 out of 10, Exceptional, (30 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 NZ$265
includes taxes & fees
11 Oct - 12 Oct
Granny Flat in leafy SW Portland
A modern living room with a large gray sectional sofa, a flat-screen TV mounted on the wall, and a wooden coffee table.

10. Suburban Studio, Near Golf, Wineries & Dining

Suburban Studio, Near Golf, Wineries & Dining
Garden Home-Whitford
The price is NZ$703
includes taxes & fees
3 Nov - 4 Nov
Suburban Studio, Near Golf, Wineries & Dining
A bedroom with a bed, desk, chair, and a small table.

11. The Grove - A Family Friendly Modern Studio in Portland/Beaverton/Hillsboro

The Grove - A Family Friendly Modern Studio in Portland/Beaverton/Hillsboro
Oak Hills
10.0 out of 10, Exceptional, (3 reviews)
"Super clean studio apartment. Very modern and up-to-date. Fabulous shower. Quality appliances and BBQ were great to have! It is helpful to have access to a car due to location. Host and family were super friendly and checked in a couple of times during my stay. Overall a wonderful experience."
United States
Michael M.
The price is NZ$486
includes taxes & fees
6 Oct - 7 Oct
The Grove - A Family Friendly Modern Studio in Portland/Beaverton/Hillsboro
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 NZ$553
includes taxes & fees
19 Oct - 20 Oct
The Laid-Back Loft | Mississippi Ave
A dining area with a wooden table and chairs, a fireplace, and a sofa in the background.

13. #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 NZ$644
includes taxes & fees
8 Oct - 9 Oct
#StayInMyDistrict Arbor Lodge The Ainsworth
A storefront with a sign for La Familia Cider Company, offering free samples and a variety of drinks.

14. 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.
The price is NZ$453
includes taxes & fees
3 Nov - 4 Nov
Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
A cozy living room with a wooden ceiling, a sofa, a coffee table, and a dining area with a table and chairs.

15. Mid-Century Hideaway, Near Forest Park

Mid-Century Hideaway, Near Forest Park
West Haven-Sylvan
The price is NZ$608
includes taxes & fees
5 Nov - 6 Nov
Mid-Century Hideaway, Near Forest Park
A modern living room with a dining area, large windows, and a fireplace.

16. ❤️ 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 NZ$693
includes taxes & fees
19 Oct - 20 Oct
❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
Interior

17. Sleeps 8 people near Vancouver waterfront and PDX

Sleeps 8 people near Vancouver waterfront and PDX
Vancouver
The price is NZ$403
includes taxes & fees
18 Oct - 19 Oct
Sleeps 8 people near Vancouver waterfront and PDX
A modern kitchen with a large island, white cabinetry, and a flat-screen TV mounted above the counter.

18. Cozy Private Cottage Near Downtown Portland

Cozy Private Cottage Near Downtown Portland
Northeast Portland
10.0 out of 10, Exceptional, (69 reviews)
"We enjoyed our stay. Convenient location. Owners were very responsive to messages. Would definitely stay here again!"
United States
Juliette L.
Cozy Private Cottage Near Downtown Portland
A wooden cabin with a front porch, a staircase, and a garden.

19. Hip and cozy dog-friendly Mississippi Victorian

Hip and cozy dog-friendly Mississippi Victorian
North Portland
10.0 out of 10, Exceptional, (16 reviews)
"Great location"
United States
Ivy S.
The price is NZ$502
includes taxes & fees
6 Oct - 7 Oct
Hip and cozy dog-friendly Mississippi Victorian
A living room with a coffee table, books, a lamp, a potted plant, and a framed picture on the wall.

20. 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.
The price is NZ$433
includes taxes & fees
14 Oct - 15 Oct
Two Rivers Relaxing Retreat
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
"Nice staff. Easy access to all parts of downtown."
Timothy 2-night trip
Posted 5 hours ago
The Royal Sonesta Portland Downtown

Find out more about Portland

Portland Holiday Homes information

Number of reviews
1,268
Accommodation
727 Holiday Homes
Lowest Price
NZ$265
Highest Price
NZ$703

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