
Vacation rentals near Pioneer Courthouse Square
We found 1,633 vacation rentals — enter your dates for availability
Choose the right private vacation rental that's close to Pioneer Courthouse Square. Vacation homes offer the amenities you expect for you and your friends, family, or even pets, like WiFi and a washer and dryer. At the end of the day, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Pioneer Courthouse Square
Showing deals for:Nov 7 - Nov 14
Image gallery for Modern Downtown Lake Oswego Home!

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Modern Downtown Lake Oswego Home!
Lake Oswego, OR
8% off
Price is $254
$254
$1,780 for 7 nights
$1,780 for 7 nights
All fees included
Image gallery for The Victorian Cottage with Mountain & River views!

9.89.8 out of 10 rating
Exceptional
(19 reviews)
The Victorian Cottage with Mountain & River views!
Portland, OR
9% off
Price is $220
$220
$1,539 for 7 nights
$1,539 for 7 nights
All fees included
Image gallery for Yeti's Tree House: Where Dreams Come True

8.48.4 out of 10 rating
Very Good
(19 reviews)
Yeti's Tree House: Where Dreams Come True
Portland, OR
9% off
Price is $175
$175
$1,226 for 7 nights
$1,226 for 7 nights
All fees included
Image gallery for Full remodeled home on 1/3rd Acre! Close to Nike WHQ and central Beaverton.

8.08.0 out of 10 rating
Very Good
(8 reviews)
Full remodeled home on 1/3rd Acre! Close to Nike WHQ and central Beaverton.
Beaverton, OR
9% off
Price is $256
$256
$1,793 for 7 nights
$1,793 for 7 nights
All fees included
Image gallery for Bike‘N’Roll Cottage: Adventure & Relaxation

1010 out of 10 rating
Exceptional
(8 reviews)
Bike‘N’Roll Cottage: Adventure & Relaxation
Portland, OR
8% off
Price is $195
$195
$1,365 for 7 nights
$1,365 for 7 nights
All fees included
Image gallery for Cozy Modern Farmhouse, King bed, great yard, pets!

1010 out of 10 rating
Exceptional
(44 reviews)
Cozy Modern Farmhouse, King bed, great yard, pets!
Milwaukie, OR
17% off
Price is $295
$295
$2,066 for 7 nights
$2,066 for 7 nights
All fees included
Image gallery for Mossy Cobbles: Romantic Cottage in a Wooded Setting

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Mossy Cobbles: Romantic Cottage in a Wooded Setting
Tigard, OR
8% off
Price is $121
$121
$850 for 7 nights
$850 for 7 nights
All fees included
Image gallery for A Grand House

1010 out of 10 rating
Exceptional
(28 reviews)
A Grand House
Vancouver, WA
8% off
Price is $188
$188
$1,315 for 7 nights
$1,315 for 7 nights
All fees included
Image gallery for Spacious, private, 5 bedrooms 3 full bath House near Portland downtown

1010 out of 10 rating
Exceptional
(13 reviews)
Spacious, private, 5 bedrooms 3 full bath House near Portland downtown
Beaverton, OR
8% off
Price is $604
$604
$4,231 for 7 nights
$4,231 for 7 nights
All fees included
Image gallery for House hot tub sauna close to PDX Airport

9.89.8 out of 10 rating
Exceptional
(13 reviews)
House hot tub sauna close to PDX Airport
Vancouver, WA
16% off
Price is $448
$448
$3,138 for 7 nights
$3,138 for 7 nights
All fees included
Image gallery for HIGHLY sought, HIGHLY ranked, spacious 4 bdrm home with unbeatable location

9.89.8 out of 10 rating
Exceptional
(7 reviews)
HIGHLY sought, HIGHLY ranked, spacious 4 bdrm home with unbeatable location
Vancouver, WA
9% off
Price is $297
$297
$2,080 for 7 nights
$2,080 for 7 nights
All fees included
Image gallery for Rare Riverside Retreat

1010 out of 10 rating
Exceptional
(17 reviews)
Rare Riverside Retreat
Milwaukie, OR
10% off
Price is $165
$165
$1,156 for 7 nights
$1,156 for 7 nights
All fees included
Image gallery for The "Old Barn" in the woods. Peace, Romance, Ahhh

8.88.8 out of 10 rating
Excellent
(25 reviews)
The "Old Barn" in the woods. Peace, Romance, Ahhh
Portland, OR
9% off
Price is $155
$155
$1,088 for 7 nights
$1,088 for 7 nights
All fees included
Image gallery for Charming Portland Home, Walk to Light Rail!

1010 out of 10 rating
Exceptional
(16 reviews)
Charming Portland Home, Walk to Light Rail!
Milwaukie, Oregon
7% off
Price is $212
$212
$1,485 for 7 nights
$1,485 for 7 nights
All fees included
Image gallery for Work or Play 5B retreat.Great Location near Nike, 15mins to downtown

1010 out of 10 rating
Exceptional
(16 reviews)
Work or Play 5B retreat.Great Location near Nike, 15mins to downtown
Beaverton, OR
8% off
Price is $447
$447
$3,127 for 7 nights
$3,127 for 7 nights
All fees included
Image gallery for Large In-Law Studio Apartment

9.89.8 out of 10 rating
Exceptional
(64 reviews)
Large In-Law Studio Apartment
Portland, OR
12% off
Price is $131
$131
$919 for 7 nights
$919 for 7 nights
All fees included
Image gallery for Beverly Heights Retreat

9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beverly Heights Retreat
Vancouver, WA
8% off
Price is $330
$330
$2,308 for 7 nights
$2,308 for 7 nights
All fees included
Image gallery for Casa Tropical Jungle in the Couve close to DT

9.49.4 out of 10 rating
Exceptional
(13 reviews)
Casa Tropical Jungle in the Couve close to DT
Vancouver, WA
12% off
Price is $120
$120
$842 for 7 nights
$842 for 7 nights
All fees included
Image gallery for Vancouver WA Home - Sleeps 6

1010 out of 10 rating
Exceptional
(9 reviews)
Vancouver WA Home - Sleeps 6
Vancouver, WA
8% off
Price is $138
$138
$964 for 7 nights
$964 for 7 nights
All fees included
Image gallery for All the Views: A Private BnB with VIEWS

1010 out of 10 rating
Exceptional
(21 reviews)
All the Views: A Private BnB with VIEWS
Happy Valley, OR
12% off
Price is $115
$115
$803 for 7 nights
$803 for 7 nights
All fees included
Image gallery for Modern, pet friendly1/3 acre home just 25 minutes to downtown Portland

9.49.4 out of 10 rating
Exceptional
(15 reviews)
Modern, pet friendly1/3 acre home just 25 minutes to downtown Portland
Milwaukie, OR
5% off
Price is $169
$169
$1,182 for 7 nights
$1,182 for 7 nights
All fees included
Image gallery for Spectacular Choice: Sleeps 6, Your Dog Welcome Too

9.89.8 out of 10 rating
Exceptional
(36 reviews)
Spectacular Choice: Sleeps 6, Your Dog Welcome Too
Tigard, OR
8% off
Price is $166
$166
$1,159 for 7 nights
$1,159 for 7 nights
All fees included
Image gallery for Upscale and quiet new home in Lake Oswego with amazing Patio

1010 out of 10 rating
Exceptional
(37 reviews)
Upscale and quiet new home in Lake Oswego with amazing Patio
Lake Oswego, OR
8% off
Price is $342
$342
$2,392 for 7 nights
$2,392 for 7 nights
All fees included
Image gallery for Private Beautiful 2 Bedroom Units w/ FAST FREE WIFI

9.49.4 out of 10 rating
Exceptional
(36 reviews)
Private Beautiful 2 Bedroom Units w/ FAST FREE WIFI
Beaverton, OR
10% off
Price is $152
$152
$1,061 for 7 nights
$1,061 for 7 nights
All fees included
Find spaces that suit your style
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Find properties near top attractions in Pioneer Courthouse Square
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Find the best place to stay - Pioneer Courthouse Square
Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
233 reviews(233 reviews)
Beautiful University Park Art House In N. Portland, Near U. Of P.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
223 reviews(223 reviews)
Quaint private cottage apt. in highly desirable area, close to everything
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
165 reviews(165 reviews)
Top rated rentals - Pioneer Courthouse Square
Nice Stay
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
The stay was excellent. Everything offered was there and more. We had a good time and if we ever go that way again we'll reserve the same place
Larry C.
Stayed Jul 2025
Just right
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
A perfect home base for our vacation in Vancouver.
Robbish
Stayed Jun 2025
Cute guest house
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Lovely little guest house north of Portland. Great parking, comfy beds, and very commincative host.
Mary V.
Stayed Jun 2025
Cozy Sellwood Stay
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Photos and description was accurate. Clean place, well stocked kitchen and bathroom
Fannie B.
Stayed Jun 2025
Beautiful Space Great Hosts
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
The space was so pretty and lovely to stay in. Hosts were kind and helpful and communicative :)
Teidyn G.
Stayed Feb 2025
Perfect getaway spot
1010 out of 10
Exceptionalexceptional
310 reviews(310 reviews)
The property was beautiful and contained everything we needed for the stay. The communication from the host was spot on and the binder of information inside the Vrbo had everything we needed to make our trip worthwhile.
Kellie D.
Stayed Feb 2025
Beautiful House
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Rachel is such a great owner and it was great working with her. We are excited to visit again!
Cassie C.
Stayed Jan 2025
Almost perfect
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
First of all, I enjoyed my stay at this property. Even though the weather was up in the 100s the basement apartment was still quite cool and comfortable. The amenities were very nice and I especially loved the harder pillows which I resulted in a restful slumber. I recommend parking on the same side of the street as the trees on the other side tend to drop fruits, flowers and leaves (perhaps some sap too) on the car.
My only issue was the lack of privacy in the living room/kitchen/dining area because of the diaphanous curtains. Thicker curtains would be nice.
Thanks for the lovely stay.
Harun R.
Stayed Jul 2024
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- More for lessMore space, more privacy, more amenities — more value