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

Happy Valley Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Happy Valley vacation 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
9.8 out of 10, Exceptional, (57 reviews)
"Wonderful experience, will stay there again if I am ever in Portland! The hot tub was such a bonus!"
United States
Amanda M.
$536 nightly
The price is $544
Oct 20 - Oct 21
Total with taxes and fees
Large Cozy Home
An outdoor patio with two black chairs and a table, a fire pit, string lights, and a wooden fence.

2. Sleek Urban Retreat in Happy Valley

Sleek Urban Retreat in Happy Valley
Happy Valley
10.0 out of 10, Exceptional, (9 reviews)
"Clean and spacious. Property as advertised. Would chose again if we come back this way!"
United States
Robert
$600 nightly
The price is $609
Oct 28 - Oct 29
Total with taxes and fees
Sleek Urban Retreat in Happy Valley
A modern kitchen with white cabinetry, a built-in oven, and a large island with a sink.

3. Spacious 4 BR house in peaceful Happy Valley with Game Room, Mahjong & Foosball

Spacious 4 BR house in peaceful Happy Valley with Game Room, Mahjong & Foosball
Happy Valley
Spacious 4 BR house in peaceful Happy Valley with Game Room, Mahjong & Foosball
A dining area with a wooden table and black chairs, a grey sofa, and a decorative clock on the wall.

4. Cozy apartment in a lovely and quiet neighborhood

Cozy apartment in a lovely and quiet neighborhood
Milwaukie
9.6 out of 10, Exceptional, (117 reviews)
"Very nice accommodation and will try again next time we visit the area."
United States
William O.
$186 nightly
The price is $189
Oct 14 - Oct 15
Total with taxes and fees
Cozy apartment in a lovely and quiet neighborhood
A modern kitchen with a large island, grey cabinets, and wooden flooring.

5. 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, (129 reviews)
"A great place to stay in the Portland,OR area!"
United States
Mary R.
$332 nightly
The price is $337
Oct 15 - Oct 16
Total with taxes and fees
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.

6. Margaux · 1967 Airstream · Garden Glamping · PDX

Margaux · 1967 Airstream · Garden Glamping · PDX
Southeast Portland
9.6 out of 10, Exceptional, (20 reviews)
"The property is very beautiful, with lots of fun little areas to hang out. It's right in the heart of the cool partof Portland."
United States
Patrick H.
$132 nightly
The price is $158
Oct 21 - Oct 22
Total with taxes and fees
Margaux · 1967 Airstream · Garden Glamping · PDX
A hotel room with a bed, bedside lamp, flat-screen TV, microwave, and a small desk with a telephone.

7. King Bed Non-Smoking

King Bed Non-Smoking
Portland OR
10.0 out of 10, Exceptional, (84 reviews)
"Loved the location, close to everything we needed!"
United States
Anonymous traveler
$89 nightly
The price is $99
Oct 13 - Oct 14
Total with taxes and fees
King Bed Non-Smoking
A dining table set with white plates, glasses, and silverware, surrounded by beige chairs and a sofa in a neutral-toned room.

8. 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.
$260 nightly
The price is $264
Oct 13 - Oct 14
Total with taxes and fees
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
A CIBO bar and restaurant with large windows, outdoor seating, and a planter with flowers.

9. Jewel in the Sky: Modern, Private, Luxurious Loft + EV Charger!

Jewel in the Sky: Modern, Private, Luxurious Loft + EV Charger!
Southeast Portland
10.0 out of 10, Exceptional, (77 reviews)
"Great location, walking distance to restaurants and bars. "
United States
Suzanne R.
$288 nightly
The price is $333
Oct 26 - Oct 27
Total with taxes and fees
Jewel in the Sky: Modern, Private, Luxurious Loft + EV Charger!
A bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

10. #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)
"Great spot a few blocks away from Foster Powell. "
United States
Jack
$189 nightly
The price is $223
Oct 13 - Oct 14
Total with taxes and fees
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
A wooden deck with a table and chairs, a green umbrella, and potted plants.

11. Beautiful Art Filled Home 15 minutes to Downtown

Beautiful Art Filled Home 15 minutes to Downtown
Ardenwald
10.0 out of 10, Exceptional, (83 reviews)
"Close to shops and restaurants."
United States
Greenie D.
$305 nightly
The price is $310
Oct 13 - Oct 14
Total with taxes and fees
Beautiful Art Filled Home 15 minutes to Downtown
A cozy living room with a wooden ceiling, a bookshelf, a television, and a door leading to a garden.

12. Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower

Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower
Northeast Portland
9.8 out of 10, Exceptional, (118 reviews)
"It was fabulous! The place was adorable and had all the amenities!! Jean was a lovely host! I could live there!"
United States
Tamara F.
$216 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower
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.

13. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Very clean, well equipted , great location, comfortable bed, great spot for coffee outside"
United States
Sorek Y.
$203 nightly
The price is $240
Oct 15 - Oct 16
Total with taxes and fees
#StayinMyDistrict Sellwood Coco Rose Retreat
A white house with a dark blue front door, a wreath, and a mailbox with the number 15908.

14. Cozy Cottage at Dragonfly Horse Ranch

Cozy Cottage at Dragonfly Horse Ranch
Oregon City
8.8 out of 10, Excellent, (15 reviews)
"We had a excellent visit. Cara was a wonderful host and everything about the cottage was comfortable, well equipped and clean. We had a very enjoyable time there.Our cat loved it there and this cat does not travel much at all. Kudos to the crewat Cozy Cottage.Sheryl and Robert"
United States
Sheryl C.
$210 nightly
The price is $213
Oct 13 - Oct 14
Total with taxes and fees
Cozy Cottage at Dragonfly Horse Ranch
A hallway with a wooden door, a mirror, a white sink, and a wooden cabinet.

15. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Portland OR
9.8 out of 10, Exceptional, (60 reviews)
"Great value for what we paid! Spacious room with all we needed for a quick stay, including nice amenities like free toiletries."
United States
Anonymous traveler
$90 nightly
The price is $101
Oct 13 - Oct 14
Total with taxes and fees
2 Queen Beds Non-Smoking
A hotel room with two beds, a desk, a TV, and a bathroom visible through an open door.

16. 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 traveler
$105 nightly
The price is $118
Oct 13 - Oct 14
Total with taxes and fees
Premium 2 Queen Bed with Kitchenette
A hotel room with a bed, bedside lamp, flat-screen TV, microwave, and a small desk with a telephone.

17. Premium King Bed with Kitchenette

Premium King Bed with Kitchenette
Portland OR
10.0 out of 10, Exceptional, (65 reviews)
"Clean bathroom and ample towels were nice after long travel days."
United States
Anonymous traveler
$97 nightly
The price is $109
Oct 14 - Oct 15
Total with taxes and fees
Premium King Bed with Kitchenette
A living room with a fireplace, a dining table with chairs, and a large window.

18. #StayinMyDistrict Gorge-Mt Hood

#StayinMyDistrict Gorge-Mt Hood
Gresham
9.6 out of 10, Exceptional, (28 reviews)
"Location was perfect. Everything was exactly what we needed. Thank you!"
United States
Dawn S.
$298 nightly
The price is $341
Oct 13 - Oct 14
Total with taxes and fees
#StayinMyDistrict Gorge-Mt Hood
A modern living room with a grey sofa, a coffee table, and a dining area with a table and chairs.

19. Modern Home in Portland

Modern Home in Portland
North Gresham
10.0 out of 10, Exceptional, (15 reviews)
"Very nice house 🙌"
United States
Edgar
$279 nightly
The price is $321
Oct 15 - Oct 16
Total with taxes and fees
Modern Home in Portland
A playground with a slide, climbing structures, and a swing set.

20. Guest Suite with WiFi, AC, streaming

Guest Suite with WiFi, AC, streaming
Southwest Portland
9.0 out of 10, Wonderful, (22 reviews)
"Space was actually much larger than I thought it would be, very clean. I was worried when I saw street parking, but it was absolutely no issue at all- located in a quiet neighborhood with lots of restaurants/cafes in walkable distance."
United States
Madison
$219 nightly
The price is $258
Oct 18 - Oct 19
Total with taxes and fees
Guest Suite with WiFi, AC, streaming
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Happy Valley Hotel Reviews

Country Inn & Suites by Radisson, Portland International Airport, OR

Country Inn & Suites by Radisson, Portland International Airport, OR

10/10 Excellent
"Nice staff"
patricia 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Portland International Airport, OR

Find out more about Happy Valley

Everything you need to know about Happy Valley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Happy Valley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Happy Valley vacation 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 low season months. For more hustle and bustle, you may prefer to visit Happy Valley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Happy Valley rentals

At Expedia, we put the best Happy Valley vacation 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 vacation.

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.

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.