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

Happy Valley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Happy Valley vacation rentals

Dining

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.
$481 nightly
The price is $488
Sep 28 - Sep 29
Total with taxes and fees
Large Cozy Home
Terrace/patio

2. 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.
$124 nightly
The price is $148
Sep 23 - Sep 24
Total with taxes and fees
Margaux · 1967 Airstream · Garden Glamping · PDX
Dining

3. 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.
$188 nightly
The price is $191
Sep 28 - Sep 29
Total with taxes and fees
Cozy apartment in a lovely and quiet neighborhood
1 bedroom

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 traveler
$90 nightly
The price is $101
Sep 21 - Sep 22
Total with taxes and fees
King Bed Non-Smoking
Coffee/tea maker, fridge, microwave, oven

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, (128 reviews)
"A great place to stay in the Portland,OR area!"
United States
Mary R.
$327 nightly
The price is $332
Oct 1 - Oct 2
Total with taxes and fees
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
TV, offices

6. #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.
$239 nightly
The price is $281
Oct 4 - Oct 5
Total with taxes and fees
#StayinMyDistrict Sellwood Coco Rose Retreat
Coffee/tea maker, fridge, microwave, oven

7. Guest Suite with WiFi, AC, streaming

Guest Suite with WiFi, AC, streaming
Southwest Portland
9.0 out of 10, Wonderful, (22 reviews)
"Nice place for us to stay while visiting family in the area. "
United States
Chris W.
Guest Suite with WiFi, AC, streaming
Interior

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.
$211 nightly
The price is $214
Sep 21 - Sep 22
Total with taxes and fees
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
Dining

9. Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products

Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products
Jennings Lodge
10.0 out of 10, Exceptional, (16 reviews)
"Had a great stay. Very clean rooms, thoughtfully stocked with the basics for cooking, laundry, etc. "
United States
Maximillian C.
Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products
1 bedroom, desk, iron/ironing board, travel crib

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
$215 nightly
The price is $253
Sep 23 - Sep 24
Total with taxes and fees
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
Dining

11. Charming 3-bedroom house in Portland

Charming 3-bedroom house in Portland
Portland
9.8 out of 10, Exceptional, (30 reviews)
"Clean, cozy, perfect for our needs!"
United States
Mildred P.
$343 nightly
The price is $394
Sep 21 - Sep 22
Total with taxes and fees
Charming 3-bedroom house in Portland
Outdoor dining

12. ★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE

★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE
Northeast Portland
9.8 out of 10, Exceptional, (169 reviews)
"Great location, quiet neighborhood. Really enjoyed our stay."
United States
Brenda L.
$294 nightly
The price is $345
Oct 21 - Oct 22
Total with taxes and fees
★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE
Coffee/tea maker, fridge, microwave, oven

13. 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.
$297 nightly
The price is $348
Sep 21 - Sep 22
Total with taxes and fees
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
Exterior

14. 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.
$289 nightly
The price is $334
Sep 21 - Sep 22
Total with taxes and fees
Jewel in the Sky: Modern, Private, Luxurious Loft + EV Charger!
Interior

15. 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, (116 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.
$217 nightly
The price is $256
Sep 21 - Sep 22
Total with taxes and fees
Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower
Interior

16. 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
$91 nightly
The price is $102
Sep 21 - Sep 22
Total with taxes and fees
2 Queen Beds Non-Smoking
Outdoor dining

17. 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.
$301 nightly
The price is $306
Sep 21 - Sep 22
Total with taxes and fees
Beautiful Art Filled Home 15 minutes to Downtown
Smart TV, table tennis

18. Modern Home in Portland

Modern Home in Portland
North Gresham
10.0 out of 10, Exceptional, (15 reviews)
"Very nice house 🙌"
United States
Edgar
$267 nightly
The price is $307
Sep 21 - Sep 22
Total with taxes and fees
Modern Home in Portland
Iron/ironing board, WiFi, bed sheets

19. Airy Studio - Private Balcony - W&D - Great locale

Airy Studio - Private Balcony - W&D - Great locale
Northeast Portland
9.4 out of 10, Exceptional, (83 reviews)
"Definitely would book this place again!"
United States
Czar N.
$270 nightly
The price is $317
Sep 21 - Sep 22
Total with taxes and fees
Airy Studio - Private Balcony - W&D - Great locale
Smart TV, fireplace, DVD player, books

20. ❤️ 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.
$312 nightly
The price is $366
Oct 13 - Oct 14
Total with taxes and fees
❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
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

Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

8/10 Good
"The staff where incredibly kind and very helpful especially if your not from Portland and trying to get around."
Pricila 1-night trip
Posted 5 hours ago
Courtyard by Marriott Portland City Center

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 $107 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 21 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 Eagle Landing Golf Course and Clackamas Town Center.

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.