Pioneer Courthouse Square showing a statue or sculpture and outdoor art

Holiday rentals near Pioneer Courthouse Square

We found 1,714 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

January 2026

February 2026

Choose the right private holiday rental that's near Pioneer Courthouse Square. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Pioneer Courthouse Square

Showing deals for:3 Apr - 10 Apr

Exceptional

(48 reviews)

Cozy Modern Farmhouse, King bed, great yard, pets!

Oak Grove

17% off

for 7 nights, 1 room

AU$439 per night

includes taxes & fees

Exceptional

(5 reviews)

Cozy 3-bed house with Mt. St. Helens View in SW Hills Portland

Portland

7% off

for 7 nights, 1 home

AU$611 per night

includes taxes & fees

Exceptional

(16 reviews)

SW Quiet Neighborhood with Territorial View. 10 min to town. Sleeps up to 8

Portland

12% off

for 7 nights, 1 apartment

AU$439 per night

includes taxes & fees

Exceptional

(14 reviews)

Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park

Lake Oswego

8% off

for 7 nights, 1 apartment

AU$263 per night

includes taxes & fees

Exceptional

(57 reviews)

Private Home, Near Nike & Intel, w/spacious yard

Beaverton

6% off

for 7 nights, 1 home

AU$349 per night

includes taxes & fees

Exceptional

(23 reviews)

Huge Luxury Home with huge Deck near Powell Butte Park

Portland

11% off

for 7 nights, 1 home

AU$1,322 per night

includes taxes & fees

Exceptional

(53 reviews)

❤️ CLEAN | LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ LARGE PATIO

Portland

7% off

for 7 nights, 1 home

AU$410 per night

includes taxes & fees

Exceptional

(41 reviews)

Spectacular Choice: Sleeps 6, Your Dog Welcome Too

Tigard

7% off

for 7 nights, 1 home

AU$316 per night

includes taxes & fees

Exceptional

(22 reviews)

Renovated Portland Single Story Home- Wine Country, Amaterra, Nike, Zoo, Intel

Portland

12% off

for 7 nights, 1 home

AU$663 per night

includes taxes & fees

Living room with firepalce, shuffleboard, plenty of seating, TV, game system. Great for family fun!

Exceptional

(9 reviews)

Book NOW for Fall Fun! - Perfect for family! - Fully Loaded! - Fire Pit!

Portland

7% off

for 7 nights, 1 home

AU$400 per night

includes taxes & fees

Chat, relax or play a board game in the charming main floor living room.

Exceptional

(20 reviews)

Stunning Remodeled 5-BR Craftsman. 4x King Beds + 2x Twin XL! With AC & Laundry

Portland

7% off

for 7 nights, 1 home

AU$836 per night

includes taxes & fees

Exceptional

(53 reviews)

Gateway to Alberta Arts, Mississippi Ave, and N. Williams Corridor

Portland

6% off

for 7 nights, 1 home

AU$497 per night

includes taxes & fees

Exceptional

(45 reviews)

Upscale and quiet new home in Lake Oswego with amazing Patio

Lake Oswego

8% off

for 7 nights, 1 home

AU$655 per night

includes taxes & fees

Newly renovated kitchen with all the essentials, a coffee bar and stylish design

Exceptional

(8 reviews)

Best Area + Beautiful 5-Bedroom Farmhouse + Oregon Themed + Serene Backyard

Portland

7% off

for 7 nights, 1 home

AU$886 per night

includes taxes & fees

Exceptional

(9 reviews)

Renovated Victorian : King Beds, AC, 95 Walk Score in Best Area.

Portland

7% off

for 7 nights, 1 home

AU$973 per night

includes taxes & fees

Architect designed interior has comfort, style, high ceilings and huge windows.

Exceptional

(17 reviews)

King Beds, Roofdeck, AC, Best Area with 95 WalkScore

Portland

7% off

for 7 nights, 1 home

AU$1,022 per night

includes taxes & fees

Exceptional

(34 reviews)

Cottage in Historic Irvington neighborhood near Convention Center and shops!

Portland

7% off

for 7 nights, 1 room

AU$251 per night

includes taxes & fees

Welcome to The Ginkgo House, free parking, no stairs, pet and family friendly

Exceptional

(59 reviews)

★ Family Friendly/Prime Location/ Lots of Amenities/ Safe/ Dog friendly ★

Portland

7% off

for 7 nights, 1 apartment

AU$415 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Pioneer Courthouse Square

Pioneer Courthouse Square

Find the best place to stay - Pioneer Courthouse Square

Our lobby blends rustic charm with upscale design, featuring stone walls and rich wooden floors, providing a cozy retreat from the bustling city.

Deluxe Room | Portland Hub + Pulitzer Display

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals - Pioneer Courthouse Square

Modern & Great Location

Had a great stay with my kids here, having the bedrooms on opposite sides was very helpful. The place was cozy, clean, and great location. Would stay here again!

Brittagh L.

Stayed Jan 2025

Queen sized bed with both feather and foam pillows, fireplace, tv, stereo, etc.

Premier Host

Portland stopover

Vicki is a very helpful and obliging host who has thought of every comfort that we might need for our stay. We were very warm and comfortable.

Marilyn B.

Stayed May 2024

Brick House Beautiful is on Nat. Historic Register - 24 different brick pattern

Premier Host

Perfect place to stay when visiting Portland

Bob was such a lovely fella, very friendly, accommodating and he even gave us a tour of the house, which is stunning. The space downstairs where we stayed had everything you could need and was very comfortable. As with the house, the backyard was lovely and perfect to unwind at the end of the day. The neighbourhood was one of the nicest I've come across. Highly recommend staying here.

Andrew S.

Stayed May 2022

Premier Host

Great home away from home

We loved our stay in this beautifully appointed apartment. Heaps of space, comfy beds, quiet, and walking distance to a big selection of eateries. Would definitely stay again 😊

Craig T.

Stayed June 2019

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Holiday rentals near Pioneer Courthouse Square

Holiday rentals with weekly discounts - Pioneer Courthouse Square

Image gallery for Cozy Modern Farmhouse, King bed, great yard, pets!

Cozy Modern Farmhouse, King bed, great yard, pets!

Find spaces that suit your style

Find properties near top attractions in Pioneer Courthouse Square

Map Attractions

Pioneer Courthouse Square

Find the best place to stay - Pioneer Courthouse Square

Deluxe Room | Portland Hub + Pulitzer Display

Top rated rentals - Pioneer Courthouse Square

Modern & Great Location

Peace of mind

More quality time

All the privacy of home

More for less

More holiday ideas