A suburban area with houses, trees, and a church.

Happy Valley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Happy Valley vacation rentals

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 CA $153
CA $713 total
includes taxes & fees
Nov 15 - Nov 16
Large Cozy Home

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 CA $176
CA $204 total
includes taxes & fees
Nov 30 - Dec 1
Inn at Northrup Station

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, (2,329 reviews)
"excellent place to stay and affordable. second time staying here and would recommend to others."
United States
Sarijah
The price is CA $120
CA $136 total
includes taxes & fees
Nov 17 - Nov 18
Larkspur Landing Extended Stay Suites Hillsboro

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 CA $278
CA $425 total
includes taxes & fees
Nov 29 - Nov 30
Beautiful Art Filled Home 15 minutes to Downtown

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 CA $235
CA $376 total
includes taxes & fees
Nov 23 - Nov 24
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard

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 CA $174
CA $459 total
includes taxes & fees
Dec 3 - Dec 4
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

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 CA $109
CA $210 total
includes taxes & fees
Nov 18 - Nov 19
Margaux · 1967 Airstream · Garden Glamping · PDX

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 CA $128
CA $247 total
includes taxes & fees
Dec 1 - Dec 2
Pomeroy

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 CA $244
CA $280 total
includes taxes & fees
Nov 16 - Nov 17
Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland

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 CA $246
CA $371 total
includes taxes & fees
Nov 14 - Nov 15
Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

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 CA $93
CA $314 total
includes taxes & fees
Nov 17 - Nov 18
#StayinMyDistrict Pendelton Place Walk to Mt Tabor

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 CA $116
CA $152 total
includes taxes & fees
Dec 3 - Dec 4
Premium 2 Queen Bed with Kitchenette

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 CA $231
CA $332 total
includes taxes & fees
Nov 15 - Nov 16
Cozy ADU with AC in charming Oregon City

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 CA $150
CA $631 total
includes taxes & fees
Nov 17 - Nov 18
Charming 3-bedroom house in Portland

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 CA $171
CA $444 total
includes taxes & fees
Nov 17 - Nov 18
Modern Home in Portland

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 CA $96
CA $319 total
includes taxes & fees
Nov 15 - Nov 16
#StayinMyDistrict Sellwood Coco Rose Retreat

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 CA $181
CA $501 total
includes taxes & fees
Nov 30 - Dec 1
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

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 CA $73
CA $269 total
includes taxes & fees
Nov 17 - Nov 18
Charming 2-bedroom in historic home

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 CA $146
CA $378 total
includes taxes & fees
Nov 16 - Nov 17
Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.

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 CA $208
CA $306 total
includes taxes & fees
Nov 14 - Nov 15
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Happy Valley Hotel Reviews

Find out more about Happy Valley

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Happy Valley. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Happy Valley?

Yes, we have vacation rentals near top attractions in Happy Valley, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers 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 vacation home rentals that Happy Valley has to offer?

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row: This vacation 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 vacation rentals will I find in Happy Valley?

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

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 vacation rentals like in Happy Valley?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Happy Valley. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.