Photo by Charles Arcudi

Hillsdale holiday lettings

We found 643 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 6 homes and other holiday rentals in Hillsdale that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. At the end of the day, you're 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 - Hillsdale

Showing deals for:7 Nov - 14 Nov

Exceptional

(15 reviews)

Modern Downtown Lake Oswego Home!

Lake Oswego, OR

7% off

£207 per night

includes taxes & fees

Exceptional

(11 reviews)

High End New Estate Home in Lake Oswego. Private suite on 1st level w/o stairs.

Lake Oswego, OR

8% off

£422 per night

includes taxes & fees

Excellent

(21 reviews)

Castle Estate in SW Portland with hot tubs, minutes from downtown Portland.

Portland, OR

11% off

£712 per night

includes taxes & fees

Kitchen w/quartz countertop & shaker cabinets. Dining area for 6. Washer & dryer

Exceptional

(46 reviews)

Private house with 3 suites. Modern, Clean & Comfortable!

Portland, OR

7% off

£261 per night

includes taxes & fees

Exceptional

(205 reviews)

Luxurious Zen Modern in the Historic N. Mississippi District. Sanitized , clean!

Portland, OR

7% off

£325 per night

includes taxes & fees

Extra large king bedroom with seating and work area.

Exceptional

(26 reviews)

Spacious, Beautiful & Private Hillside Oasis, SW Hills PDX with Free Coffee!

Portland, OR

7% off

£111 per night

includes taxes & fees

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

Exceptional

(310 reviews)

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

Portland, OR

7% off

£192 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Hillsdale

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

Top rated rentals - Hillsdale

Premier Host

Home away from home in a great neighborhood

A great apartment in a great neighborhood. The perfect place to call home with great restaurants on your doorstep. What's more, Ashley is a great host. Clear communication throughout. Would stay again without a second thought.

William R.

Stayed Dec 2021

Premier Host

Well kept property in convenient locstion

This property is in really good condition, very comfortable and ten mintues walk in different directions to Pikes Place and Space Needle. The owner arranged for a very helpful young lady who lives in the same building to check us in and she was very forthcoming with recommendations for local amenities. The artisan bakery and swimming pool both in the complex were added bonuses. I am always concerned with noise and this was as a quite as one can reasonable expect in a city - no neighbour noise and just the slight my audible ventilation shaft from the pool and distant traffic noise both of which we only noticed on first arrival and overall caused us no concern. I would certainly stay here again.

Helen C.

Stayed Aug 2016

Frequently asked questions

What is the most popular type of holiday rental accommodation in Hillsdale?

The most desirable types of holiday rentals in Hillsdale are houses. After something a little different? Vrbo has a variety of options to match our guests' unique needs, so you'll see properties in all sizes and shapes. The perfect home away from home is waiting for you — find yours today.

How much does it cost to rent a holiday rental in Hillsdale?

Season, property type and length of stay are some things that can affect the price of a holiday home. Simply add your dates of travel to find your ideal match. From cosy country cottages to sprawling luxury villas, all Vrbo holiday rentals provide unbeatable value.

How much does it cost to rent a beach house in Hillsdale?

The average price for a holiday rental close to the beach in Hillsdale depends on when you're visiting the area and the size and style of property you're looking for. You can easily find prices on Vrbo by entering your preferred travel dates. Then use the filter tool to select the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday rentals in Hillsdale?

Yes, there are. You can choose from 11 holiday rentals that allow pets in Hillsdale. Some of our pet-friendly holiday rentals have an outdoor space for your fur child to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.

What are popular rental amenities in Hillsdale?

The most popular rental amenities guests are looking for in Hillsdale are mountain views, nearby museums and a garden. Whether you're hitting the road with friends, family or even pets, Vrbo holiday homes come with the best amenities for making epic memories with the people that matter most.

Are there large group holiday rentals in Hillsdale?

You'll find four holiday homes in Hillsdale that can accommodate five or more guests. From family getaways to special occasions like birthday parties, these stays have ample space to spend time with your favourite people.

Are there holiday rentals in Hillsdale that welcome kids?

Bring the whole family together for an adventure in Hillsdale at one of our 11 family-friendly holiday rentals. Lots of these stays provide conveniences that are suitable for getaways with youngsters, such as full kitchens, bunk beds and patios. Simply check the "Properties good for families" filter and choose your favourite option.

What are the top attractions for families in Hillsdale?

Keeping the kids occupied during your holiday in Hillsdale is a snap with these family-friendly attractions:

Oregon Zoo
Oregon Museum of Science and Industry
Oaks Amusement Park

Are there one-bedroom holiday rentals in Hillsdale?

Yes, you can take your pick from three one-bedroom rentals in Hillsdale. Whether you're searching for a cosy chalet or an upmarket condo, our one-bedroom properties are perfect if you don't need lots of room. One of the main perks of having your own digs? You won't have to share your trip with strangers.

Can I find two-bedroom holiday rentals in Hillsdale?

Hillsdale has six two-bedroom holiday rentals for you to pick from. Enjoy a holiday home with all the comfort and space you need at a fantastic price on Vrbo.

Are there holiday rentals with WiFi in Hillsdale?

Whether you'd like to keep up with world events, send a few emails or update your social media, there are three holiday homes with WiFi in Hillsdale. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find holiday rentals with air conditioning in Hillsdale?

Choose from six holiday homes with air conditioning in Hillsdale offering that gentle, cool breeze and extra comfort level. Simply enter your dates of travel and then make use of our filter tool to help you locate properties with air conditioning.

How old do you have to be to rent a holiday rental in Hillsdale?

The minimum age permitted can differ between properties on Vrbo, so check the rules of the holiday home in Hillsdale you're considering. But normally, it's 16, 18 or 21.

How long can I rent a holiday rental in Hillsdale for?

It's up to the Hillsdale property. To look over a list of options offering extended stays, simply enter your travel dates and number of people into Vrbo's search page. You can enjoy having the whole property to yourself, along with comforts such as a full kitchen, air conditioning and an outdoor space where the kids can run around and play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.