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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 NZ$860
includes taxes & fees
6 Oct - 7 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
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 NZ$273
includes taxes & fees
30 Sept - 1 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.

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
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 NZ$384
includes taxes & fees
1 Oct - 2 Oct
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, (129 reviews)
"A great place to stay in the Portland,OR area!"
United States
Mary R.
The price is NZ$584
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 NZ$607
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 NZ$657
includes taxes & fees
4 Oct - 5 Oct
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, (32 reviews)
"Clean, cozy, perfect for our needs!"
United States
Mildred P.
The price is NZ$613
includes taxes & fees
1 Oct - 2 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 NZ$681
includes taxes & fees
19 Oct - 20 Oct
❤️ 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.
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 NZ$181
includes taxes & fees
28 Oct - 29 Oct
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 NZ$517
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 NZ$195
includes taxes & fees
30 Sept - 1 Oct
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 NZ$470
includes taxes & fees
7 Oct - 8 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)
"Very clean, well equipted , great location, comfortable bed, great spot for coffee outside"
United States
Sorek Y.
The price is NZ$452
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, (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.
The price is NZ$371
includes taxes & fees
4 Oct - 5 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.
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 NZ$211
includes taxes & fees
4 Oct - 5 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 NZ$538
includes taxes & fees
1 Oct - 2 Oct
#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

Mark Spencer Hotel

Mark Spencer Hotel

10/10 Excellent
"Fantastic boutique Hotel right in the middle of everything that Portland has to offer downtown. We loved it and we will stay there again."
will 1-night trip
Posted 5 hours ago
Mark Spencer Hotel

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$175 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. 

Explore a world of travel with Expedia

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.