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

Happy Valley Holiday Rentals

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Check prices for these dates

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

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
9.8 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.
The price is HK$928
HK$4,256 total
includes taxes & fees
20 Oct - 21 Oct
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
The price is HK$2,129
HK$5,204 total
includes taxes & fees
28 Oct - 29 Oct
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.
The price is HK$746
HK$1,498 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$957
HK$2,661 total
includes taxes & fees
18 Oct - 19 Oct
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
9.8 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 HK$600
HK$1,229 total
includes taxes & fees
21 Oct - 22 Oct
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 traveller
The price is HK$598
HK$777 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$1,295
HK$2,183 total
includes taxes & fees
19 Oct - 20 Oct
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.
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
The price is HK$518
HK$1,791 total
includes taxes & fees
19 Oct - 20 Oct
#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.
The price is HK$1,530
HK$2,581 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is HK$542
HK$2,080 total
includes taxes & fees
2 Nov - 3 Nov
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.
The price is HK$628
HK$1,949 total
includes taxes & fees
20 Oct - 21 Oct
#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)
"My family and our dog had a quick overnight at Dragonfly Ranch, the hosts were very nice and accommodating! The home is very comfortable and had everything we needed. We love traveling with our dog so this place was perfect for us, we especially liked having a fenced yard for him to safely enjoy time outside with us."
United States
Kelsey H.
The price is HK$1,052
HK$1,666 total
includes taxes & fees
19 Oct - 20 Oct
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 traveller
The price is HK$606
HK$788 total
includes taxes & fees
18 Oct - 19 Oct
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 traveller
The price is HK$708
HK$920 total
includes taxes & fees
18 Oct - 19 Oct
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 traveller
The price is HK$650
HK$850 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$808
HK$2,694 total
includes taxes & fees
18 Oct - 19 Oct
#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
The price is HK$1,000
HK$2,630 total
includes taxes & fees
9 Nov - 10 Nov
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)
"This was a very handy place for my Portland visit with nearby services and a trail along the River you could run or walk on for many miles."
United States
Jim M.
The price is HK$507
HK$2,028 total
includes taxes & fees
20 Oct - 21 Oct
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.
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Top Happy Valley Hotel Reviews

The Royal Sonesta Portland Downtown

The Royal Sonesta Portland Downtown

10/10 Excellent
"Love the ambiance"
Maria 4-night trip
Posted 3 hours ago
The Royal Sonesta Portland Downtown

Find out more about Happy Valley

Search for holiday rentals in Happy Valley on Expedia! You can easily find your home rentals, villas, holiday apartments in Happy Valley using one of the methods below:

  • View our selection of featured holiday rentals in Happy Valley
  • Use the map to find apartments and other holiday homes in the Happy Valley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Happy Valley while they last

Look no further and take a look at our great range of rental properties in Happy Valley!

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.