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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Happy Valley vacation homes

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
9.6 out of 10, Exceptional, (55 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 CA $193
CA $624 total
includes taxes & fees
Sep 15 - Sep 16
Large Cozy Home
A spacious kitchen with a large island, dark wood flooring, and pendant lighting.

2. Luxury 5BD 4BT Home, 15min to DT Portland, Game Room, NatureTrails, Free Parking

Luxury 5BD 4BT Home, 15min to DT Portland, Game Room, NatureTrails, Free Parking
Bethany
10.0 out of 10, Exceptional, (6 reviews)
"Was an awesome house, thank you!"
United States
Les L.
The price is CA $570
CA $1,594 total
includes taxes & fees
Sep 8 - Sep 9
Luxury 5BD 4BT Home, 15min to DT Portland, Game Room, NatureTrails, Free Parking
A dining table set with white plates, glasses, and silverware, surrounded by beige chairs and a sofa in a neutral-toned room.

3. Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard

Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
Oatfield
10.0 out of 10, Exceptional, (18 reviews)
"Beautifully updated and decorated!! Felt very comfortable and perfect location! Definitely would stay there again!!"
United States
Sandy D.
The price is CA $151
CA $289 total
includes taxes & fees
Sep 7 - Sep 8
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
A modern kitchen with a large island, grey cabinets, and wooden flooring.

4. 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, (126 reviews)
"A great place to stay in the Portland,OR area!"
United States
Mary R.
The price is CA $169
CA $469 total
includes taxes & fees
Oct 1 - Oct 2
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dark wooden island with two chairs.

5. Cozy small home one bedroom

Cozy small home one bedroom
Portland
9.2 out of 10, Wonderful, (5 reviews)
"Good location and had everything we required."
United States
David B.
The price is CA $88
CA $477 total
includes taxes & fees
Sep 12 - Sep 13
Cozy small home one bedroom
A modern kitchen with white cabinets, stainless steel appliances, and a central island with seating.

6. Charming 3-bedroom house in Portland

Charming 3-bedroom house in Portland
Portland
9.8 out of 10, Exceptional, (29 reviews)
"Clean, cozy, perfect for our needs!"
United States
Mildred P.
The price is CA $113
CA $511 total
includes taxes & fees
Sep 9 - Sep 10
Charming 3-bedroom house in Portland
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 CA $153
CA $482 total
includes taxes & fees
Sep 9 - Sep 10
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
A modern living room with a grey sofa, a coffee table, and a dining area with a table and chairs.

8. 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 CA $159
CA $440 total
includes taxes & fees
Sep 7 - Sep 8
Modern Home in Portland
A white house with a dark blue front door, a wreath, and a mailbox with the number 15908.

9. Cozy Cottage at Dragonfly Horse Ranch

Cozy Cottage at Dragonfly Horse Ranch
Oregon City
8.8 out of 10, Excellent, (12 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 CA $185
CA $293 total
includes taxes & fees
Sep 11 - Sep 12
Cozy Cottage at Dragonfly Horse Ranch
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 CA $138
CA $381 total
includes taxes & fees
Oct 4 - Oct 5
#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 CA $255
CA $428 total
includes taxes & fees
Sep 23 - Sep 24
Beautiful Art Filled Home 15 minutes to Downtown

12. Guest Suite with WiFi, AC, streaming

Guest Suite with WiFi, AC, streaming
Southwest Portland
9.0 out of 10, Wonderful, (21 reviews)
"Nice place for us to stay while visiting family in the area. "
United States
Chris W.
The price is CA $88
CA $352 total
includes taxes & fees
Sep 10 - Sep 11
Guest Suite with WiFi, AC, streaming
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, (42 reviews)
"Perfect location in the heart of Sellwood."
United States
Karen V.
The price is CA $148
CA $396 total
includes taxes & fees
Oct 4 - Oct 5
#StayinMyDistrict Sellwood Coco Rose Retreat
A modern living room with a dining area, large windows, and a fireplace.

14. ❤️ 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 CA $280
CA $607 total
includes taxes & fees
Sep 29 - Sep 30
❤️ LUXURY GUESTHOUSE ★ NEAR DOWNTOWN ★ SPA BATH ★ LARGE PATIO
A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

15. Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!

Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
Southeast Portland
10.0 out of 10, Exceptional, (11 reviews)
"This is an amazing location. Walkability is excellent and the property is so quaint. We would love to stay here again. "
United States
Arlene L.
The price is CA $169
CA $401 total
includes taxes & fees
Oct 1 - Oct 2
Cozy 1-bedroom House ~ Heart of Iconic Portland Hawthorne District!!
A two-story house with a covered porch and a garden.

16. Pet friendly apartment with covered patio and fenced-in yard.

Pet friendly apartment with covered patio and fenced-in yard.
Southeast Portland
9.8 out of 10, Exceptional, (347 reviews)
"Great stay"
United States
Jack M.
The price is CA $154
CA $273 total
includes taxes & fees
Sep 15 - Sep 16
Pet friendly apartment with covered patio and fenced-in yard.
A wooden deck with a glass door leading to a forested area.

17. Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing

Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing
Rosemont Summit
8.4 out of 10, Very good, (26 reviews)
"Nice, clean place in a good neighborhood."
United States
Andrew M.
The price is CA $161
CA $270 total
includes taxes & fees
Sep 8 - Sep 9
Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing
A modern kitchen with a large island, stainless steel appliances, and a view into a living area with a high ceiling and skylight.

18. 2BR Upper unit - Sleeps 4 - Trendy Area - Walk Everywhere

2BR Upper unit - Sleeps 4 - Trendy Area - Walk Everywhere
Southeast Portland
The price is CA $175
CA $376 total
includes taxes & fees
Sep 14 - Sep 15
2BR Upper unit - Sleeps 4 - Trendy Area - Walk Everywhere
Two Adirondack chairs facing a scenic view of a mountainous landscape.

19. Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

Springdale Farm & Views - the Gorge, Downtown, Mt. Hood
Troutdale
10.0 out of 10, Exceptional, (124 reviews)
"Such a beautiful location! First time ever here in Oregon and we could not have picked a better place to stay! The views were beautiful, and the host was so kind and helpful. I would recommend this place to anybody!!"
United States
Malka
The price is CA $163
CA $281 total
includes taxes & fees
Sep 8 - Sep 9
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood
A house with a brick facade, a chimney, and a front yard with various plants and a tree.

20. Exquisite Historic Suite Close to Downtown 14-21673

Exquisite Historic Suite Close to Downtown 14-21673
Southwest Portland
10.0 out of 10, Exceptional, (547 reviews)
"A wonderful stay in Portland. A beautiful place, very clean and comfortable and a friendly and welcoming host. Would 100% recommend."
United Kingdom
Celine
The price is CA $152
CA $214 total
includes taxes & fees
Oct 5 - Oct 6
Exquisite Historic Suite Close to Downtown 14-21673
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

Heathman Lodge

Heathman Lodge

10/10 Excellent
"The gym is not what is advertised, the treadmill and bike weren’t working - not really a gym!"
Angela 1-night trip
Posted 1 hour ago
Heathman Lodge

Find out more about Happy Valley

Happy Valley Vacation Homes information

Number of reviews
1,462
Accommodation
971 Vacation Homes
Lowest Price
CA $214
Highest Price
CA $1,594

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