Happy Valley Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Happy Valley holiday rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

1. Large Cozy Home

Large Cozy Home
Southgate
9.6 out of 10, Exceptional, (60 reviews)
"Very nice place, comfortable beds, and very clean! We enjoyed our stay very much!"
United States
Breanna D.
The price is NZ$899
includes taxes & fees
15 Nov - 16 Nov
Large Cozy Home
A building with multiple balconies, outdoor seating, and a palm tree.

2. Inn at Northrup Station

Inn at Northrup Station
3.0 star property
Northwest Portland
9.4 out of 10, Exceptional, (2,287 reviews)
"Really enjoyed our stay. The ambiance is very Portland! The staff was so helpful too."
United States
Celia
The price is NZ$257
includes taxes & fees
30 Nov - 1 Dec
Inn at Northrup Station
A stone facade with a sign for Larkspur Landing Home Suite Hotel, a lantern, and a flower bed.

3. Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2,330 reviews)
"excellent place to stay and affordable. second time staying here and would recommend to others."
United States
Sarijah
The price is NZ$170
includes taxes & fees
15 Nov - 16 Nov
Larkspur Landing Extended Stay Suites Hillsboro
A wooden deck with a table and chairs, a green umbrella, and potted plants.

4. Beautiful Art Filled Home 15 minutes to Downtown

Beautiful Art Filled Home 15 minutes to Downtown
Ardenwald
10.0 out of 10, Exceptional, (85 reviews)
"Close to shops and restaurants."
United States
Greenie D.
The price is NZ$537
includes taxes & fees
29 Nov - 30 Nov
Beautiful Art Filled Home 15 minutes to Downtown
A dining table set with white plates, glasses, and silverware, surrounded by beige chairs and a sofa in a neutral-toned room.

5. Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard

Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
Oatfield
9.8 out of 10, Exceptional, (19 reviews)
"The house was clean and really cute. The set up was great for our stay and host was super helpful. Really enjoyed our stay!"
United States
Dana F.
The price is NZ$467
includes taxes & fees
23 Nov - 24 Nov
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
A modern kitchen with a large island, grey cabinets, and wooden flooring.

6. Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Milwaukie
9.4 out of 10, Exceptional, (130 reviews)
"Great location quiet neighborhood clean home with a nice yard and surroundings. Note that is it a shared property with main home but in separate quarters which was no issue to us as it was a very enjoyable stay."
United States
Karin S.
The price is NZ$569
includes taxes & fees
10 Dec - 11 Dec
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
A porch with a wooden bench, a cushioned chair, and a small table. There is a white railing and greenery in the background.

7. Margaux · 1967 Airstream · Garden Glamping · PDX

Margaux · 1967 Airstream · Garden Glamping · PDX
Southeast Portland
9.8 out of 10, Exceptional, (21 reviews)
"Great stay at Kayla's Airstream, Margaux. Perfect location and wonderful host. Highly recommend!"
United States
marcus c.
The price is NZ$249
includes taxes & fees
16 Nov - 17 Nov
Margaux · 1967 Airstream · Garden Glamping · PDX
A room with a bed, a green sofa, a mirror, and a door leading to another room.

8. Pomeroy

Pomeroy
2.0 star property
Northwest Portland
10.0 out of 10, Exceptional, (2 reviews)
"The location of this VRBO was wonderful. Lots of great food options and shopping within easy, safe walking distance. There’s a grocery store 2 blocks away. For those who want to use public transport, the #15 stops at the corner."
United States
Richard
The price is NZ$328
includes taxes & fees
1 Dec - 2 Dec
Pomeroy
A backyard with a wooden deck, a stone fountain, and a view of a lake.

9. Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland

Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland
Bolton
10.0 out of 10, Exceptional, (26 reviews)
"Just loved the music vibe. Well appointed it’s all those little things I always seem to forget. Loved watching the eagles too"
United States
Robert
The price is NZ$354
includes taxes & fees
16 Nov - 17 Nov
Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland
A living room with a TV, fireplace, and a sliding glass door leading to a balcony.

10. Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream
2.0 star property
Rosemont Summit
10.0 out of 10, Exceptional, (1 review)
The price is NZ$469
includes taxes & fees
7 Dec - 8 Dec
Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream
A bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

11. #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)
"Cozy"
United States
Brian K.
The price is NZ$401
includes taxes & fees
17 Nov - 18 Nov
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
A hotel room with two beds, a desk, a TV, and a bathroom visible through an open door.

12. Premium 2 Queen Bed with Kitchenette

Premium 2 Queen Bed with Kitchenette
Portland OR
10.0 out of 10, Exceptional, (51 reviews)
"Nice little budget friendly motel. Loved having snacks available from the vending machine on site while relaxing in our room."
United States
Anonymous traveller
The price is NZ$192
includes taxes & fees
3 Dec - 4 Dec
Premium 2 Queen Bed with Kitchenette
Living area

13. Cozy ADU with AC in charming Oregon City

Cozy ADU with AC in charming Oregon City
Oregon City
10.0 out of 10, Exceptional, (5 reviews)
"Literally a perfect stay. Great host, great space, comfortable bed, very clean and cozy. Hope to visit again. "
United States
John T.
The price is NZ$416
includes taxes & fees
15 Nov - 16 Nov
Cozy ADU with AC in charming Oregon City
A modern kitchen with white cabinets, stainless steel appliances, and a central island with seating.

14. Charming 3-bedroom house in Portland

Charming 3-bedroom house in Portland
Portland
9.8 out of 10, Exceptional, (35 reviews)
"The home was very nicely updated, clean and comfortable. Would definitely stay here again"
United States
Serena W.
The price is NZ$777
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom house in Portland
A modern living room with a grey sofa, a coffee table, and a dining area with a table and chairs.

15. Modern Home in Portland

Modern Home in Portland
North Gresham
10.0 out of 10, Exceptional, (15 reviews)
"Very nice house 🙌"
United States
Edgar
The price is NZ$537
includes taxes & fees
16 Nov - 17 Nov
Modern Home in Portland
A living room with a brown leather sofa, a striped armchair, a white coffee table, a flat-screen TV mounted on the wall, and a window with an umbrella outside.

16. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Great location near Sellwood shops & tea, bakery & restaurants."
United States
dan v.
The price is NZ$402
includes taxes & fees
15 Nov - 16 Nov
#StayinMyDistrict Sellwood Coco Rose Retreat
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

17. Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views
Southwest Portland
10.0 out of 10, Exceptional, (136 reviews)
"The place was very comfortable. Highly recommended."
United States
Raymond C.
The price is NZ$619
includes taxes & fees
30 Nov - 1 Dec
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views
A blue house with a white porch and a pathway leading to it.

18. Charming 2-bedroom in historic home

Charming 2-bedroom in historic home
Southeast Portland
9.6 out of 10, Exceptional, (49 reviews)
"Convenient and close to eateries."
United States
Dan O.
The price is NZ$339
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom in historic home
A cozy living room with a stone fireplace, a brown sofa, a wooden coffee table, and a lamp.

19. Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.

Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.
Oak Grove
9.0 out of 10, Wonderful, (20 reviews)
"This was a very comfortable stay, Some quirky features, which give it character. Nice neighbors and neighborhood. We enjoyed our stay very much! Nothing over extravagant, just basic furniture."
United States
Vivian K.
The price is NZ$472
includes taxes & fees
16 Nov - 17 Nov
Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.
A rustic outdoor seating area with benches and picnic tables, surrounded by dense forest.

20. Creekside Haven

Creekside Haven
Wilsonville
10.0 out of 10, Exceptional, (78 reviews)
"Great location and property and hosts. Would definitely stay again."
United States
Ginny S.
The price is NZ$375
includes taxes & fees
16 Nov - 17 Nov
Creekside Haven
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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Find holiday rentals that suit your style

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Top Happy Valley Hotel Reviews

An outdoor seating area with a fire feature, stone accents, and a view of a parking lot.
Holiday Inn Express & Suites Portland Airport - Cascade Stn by IHG

Holiday Inn Express & Suites Portland Airport - Cascade Stn by IHG

Holiday Inn Express & Suites Portland Airport - Cascade Stn by IHG
Northeast Portland

10/10 Excellent

Excellent stay if you need to overnight near the airport or Cascade station. Very clean & tidy rooms, perfect location as it's right near transportation. Amenities are great, Buffet breakfast & a free airport shuttle is an excellent add on. Would just suggest, having a swipe key access to the lifts for extra safety. Really enjoyed my stay, thank you so much.
Australia
Nina
Reviewed November 10, 2026
Holiday Inn Express & Suites Portland Airport - Cascade Stn by IHG

Find out more about Happy Valley

Everything you need to know about Happy Valley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Happy Valley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Happy Valley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Happy Valley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Happy Valley. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Happy Valley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Happy Valley holiday rentals we have selected for you start as low as NZ$165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Happy Valley rentals

At Expedia, we put the best Happy Valley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Happy Valley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Happy Valley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Happy Valley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there holiday rentals in Happy Valley?

Yes, there are holiday rentals close to the most popular sights in Happy Valley, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Happy Valley has a good selection of restaurants. Make sure you have time to check out the shopping and forests during your trip.

What are some of the best holiday rentals that Happy Valley has to offer?

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row: This holiday home rental outside of Happy Valley is located on a river, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Happy Valley?

Choose from 22 Expedia holiday rentals in Happy Valley for a memorable holiday.

What can I see and do in Happy Valley?

Explore the area and family-friendly sights such as Oaks Amusement Park, or get out into nature at a spot like Mount Scott. Other places in town to visit include Clackamas Town Center and Eagle Landing Golf Course.

What are holiday rentals like in Happy Valley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Happy Valley. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.

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