Photo by Charles Arcudi

Hillsdale rentals with pool

We found 438 rentals with pool — enter your dates for availability

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August 2025

September 2025

Explore Hillsdale rentals with pools

Welcome to your Portland vacation home! Fully covered front porch! TONS of charm...

3 miles from downtown Portland- The Pumpkin House

Sleeps 5 · 2 bedrooms · 1 bathroom

MCM home with atrium & yoga area near Nike HQ, Intel & Washington Square Mall

Sleeps 6 · 3 bedrooms · 2 bathrooms

Top rated rentals with pools - Hillsdale

Premier Host

Hidden gem

Tucked away and yet close to a lot of facilities we needed to go too. A lot of options for entertainment inside and out the place. Hope to stay here again when we visit Portland.

Bianca A.

Stayed Dec 2024

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

fully private and lovely guest home with private deck and dimmable lights

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

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