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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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$944
HK$3,578 total
includes taxes & fees
28 Sept - 29 Sept
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$1,932
HK$4,691 total
includes taxes & fees
19 Oct - 20 Oct
Sleek Urban Retreat in Happy Valley
A porch with a wooden bench, a cushioned chair, and a small table. There is a white railing and greenery in the background.

3. Margaux · 1967 Airstream · Garden Glamping · PDX

Margaux · 1967 Airstream · Garden Glamping · PDX
Southeast Portland
9.6 out of 10, Exceptional, (19 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.
The price is HK$586
HK$1,212 total
includes taxes & fees
29 Sept - 30 Sept
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.

4. 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$609
HK$791 total
includes taxes & fees
30 Sept - 1 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.

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 HK$902
HK$1,672 total
includes taxes & fees
29 Sept - 30 Sept
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, (128 reviews)
"A great place to stay in the Portland,OR area!"
United States
Mary R.
The price is HK$957
HK$2,492 total
includes taxes & fees
5 Oct - 6 Oct
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
A modern kitchen with white cabinets, a central island, and yellow chairs.

7. BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT

BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
Northeast Portland
9.8 out of 10, Exceptional, (21 reviews)
"Our stay was excellent. The spaceas spacious, clean and in great location for our needs "
United States
Trevor M.
The price is HK$868
HK$2,585 total
includes taxes & fees
7 Oct - 8 Oct
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
A CIBO bar and restaurant with large windows, outdoor seating, and a planter with flowers.

8. 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, (76 reviews)
"Great location, walking distance to restaurants and bars. "
United States
Suzanne R.
The price is HK$831
HK$2,588 total
includes taxes & fees
27 Sept - 28 Sept
Jewel in the Sky: Modern, Private, Luxurious Loft + EV Charger!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with seating.

9. Charming 3-bedroom house in Portland

Charming 3-bedroom house in Portland
Portland
9.8 out of 10, Exceptional, (31 reviews)
"Clean, cozy, perfect for our needs!"
United States
Mildred P.
The price is HK$824
HK$2,941 total
includes taxes & fees
30 Sept - 1 Oct
Charming 3-bedroom house in Portland
A modern living room with a dining area, large windows, and a fireplace.

10. ❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO

❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
Northeast Portland
10.0 out of 10, Exceptional, (58 reviews)
"Close to Starbucks "
United States
J J.
The price is HK$981
HK$2,525 total
includes taxes & fees
29 Sept - 30 Sept
❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
A covered patio area with seating and string lights.

11. Cozy Cully Suite with Private Patio + Near PDX

Cozy Cully Suite with Private Patio + Near PDX
Northeast Portland
10.0 out of 10, Exceptional, (32 reviews)
"Nice, little studio. Great location"
United States
Jakub K.
The price is HK$607
HK$1,600 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Cully Suite with Private Patio + Near PDX
A hallway with a wooden door, a mirror, a white sink, and a wooden cabinet.

12. 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$610
HK$794 total
includes taxes & fees
27 Sept - 28 Sept
2 Queen Beds Non-Smoking
A modern living room with a grey sofa, a coffee table, and a dining area with a table and chairs.

13. 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$900
HK$2,388 total
includes taxes & fees
30 Sept - 1 Oct
Modern Home in Portland
A hotel room with a bed, bedside lamp, flat-screen TV, microwave, and a small desk with a telephone.

14. 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$662
HK$867 total
includes taxes & fees
27 Sept - 28 Sept
Premium King Bed with Kitchenette
A bedroom with a bed, a desk, a chair, a television, and a brick fireplace.

15. #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$737
HK$2,033 total
includes taxes & fees
5 Oct - 6 Oct
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
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)
"Perfect location in the heart of Sellwood."
United States
Karen V.
The price is HK$690
HK$1,973 total
includes taxes & fees
4 Oct - 5 Oct
#StayinMyDistrict Sellwood Coco Rose Retreat
A white house with a dark blue front door, a wreath, and a mailbox with the number 15908.

17. Cozy Cottage at Dragonfly Horse Ranch

Cozy Cottage at Dragonfly Horse Ranch
Oregon City
8.8 out of 10, Excellent, (14 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.
The price is HK$1,052
HK$1,625 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage at Dragonfly Horse Ranch
A two-story house with a red exterior, a wooden staircase, and a garden with various plants.

18. Walkable Sellwood 2BR Apartment

Walkable Sellwood 2BR Apartment
Southeast Portland
10.0 out of 10, Exceptional, (109 reviews)
"This VRBO apartment is so comfortable and well designed that we hope to stay again on our next visit. It is wonderfully located and charming."
United States
Jane F.
The price is HK$1,176
HK$2,313 total
includes taxes & fees
28 Sept - 29 Sept
Walkable Sellwood 2BR Apartment
A hotel room with two beds, a desk, a TV, and a bathroom visible through an open door.

19. 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$720
HK$936 total
includes taxes & fees
30 Sept - 1 Oct
Premium 2 Queen Bed with Kitchenette
A house with a patio area featuring two green chairs and a table, a fire pit, and a bicycle parked outside.

20. #StayInMyDistrict Lake Oswego Honey Bee Cottage

#StayInMyDistrict Lake Oswego Honey Bee Cottage
First Addition
9.6 out of 10, Exceptional, (42 reviews)
"Located in a quiet, enjoyable neighborhood of Lake Oswego. Walking to shops and restaurants, or hiking in Tryon Creek is easily accessible. Property was clean and necessary items provided. I very much enjoyed my stay."
United States
Carrie
The price is HK$1,059
HK$2,323 total
includes taxes & fees
27 Sept - 28 Sept
#StayInMyDistrict Lake Oswego Honey Bee Cottage
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

Hyatt House Portland/Downtown

Hyatt House Portland/Downtown

10/10 Excellent
"Very nice property just off the river walk. Residential neighborhood. Valet parking is $55/night. However, staff pointed us to an auto-pay garage down the street which is only $24 for an overnight stay."
Steven 4-night trip
Posted less than an hour ago
Hyatt House 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 21 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 Eagle Landing Golf Course and Clackamas Town Center.

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.