Vacation rentals in Happy Valley

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Top-rated vacation rentals in Happy Valley

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Guest favorite

Guest suite in Troutdale

4.97 out of 5 average rating, 767 reviews

Amazing VIEW & Private Entry/Jetted Tub near Falls

Enjoy relaxing NO CHORES TO DO beautiful view from private balcony and bedroom! Comfy King size bed, walk- in closet, writing desk and 2 chairs. TV and WiFi . Only 17 minutes drive from the Airport and super close to many waterfalls,hiking trails and 4 minutes to Edgefield, 5 miles from Blue lake, a few minutes from Multnomah Falls, Bridal Veil Falls, and so many others Gorge falls and hiking trails, Columbia river adventures. it is located in safe neighborhood. Ask about a romantic package!

Mar 19 – 26

G$27,551 GYD per night

Guest favorite

Guest suite in Clackamas

4.95 out of 5 average rating, 255 reviews

Stunning Mt. Hood Views suite, one mile to Kaiser!

Welcome to our private suite w/a private entrance to a classic contemporary w/ a mix of modern vintage decor & hand-scraped African walnut hard wood floor located on a cul-de-sac w/gorgeous Sunrise Mt. Hood Views where you may meet a family of deer in the back yard surrounded by the green outdoors. A hiking trail. where it's quiet yet close to so much, the biggest shopping mall in Oregon-Clackamas Town Center, Kaiser Hospital, Costco, Urban Food Carts are all 1.5 mls away, 15 mins to downtown!

Oct 5 – 12

G$23,225 GYD per night

Guest favorite

Apartment in Happy Valley

4.98 out of 5 average rating, 366 reviews

All the Views: Private AirBnB, near Portland!

Guests tell us they love the view! They also mention this downstairs apartment is really clean, spacious, comfortable and relaxing (even though the high speed WiFi is great for work). • 750 square feet of privacy with a private garage entrance • Full kitchen, queen size bed, blazing fast wifi • Leather furniture, large screen TV with HDMI capability (streaming only) • Private staircase leads to your garage entrance, with no shared spaces Level 2 EV charger (let us know ahead)

Oct 26 – Nov 2

G$25,212 GYD per night

Guest favorite

Guest suite in Happy Valley

4.92 out of 5 average rating, 230 reviews

Hagen Hill BnB - Comfy Country, close to the City.

Near Mt Hood Wilderness (45mins) and Downtown Portland (30mins). Our large (1,200sq ft) downstairs space (private access) is fully yours, it has a private bedroom, bathroom, playful common room with a fireplace, pool table and dart board setup, a kitchenette and laundry facility (additional fee for laundry use). Our style invites you to take in the park-like view while relaxing comfortably. Come, Enjoy! Please note - we provide parking for ONE vehicle, if more is needed please let us know.

Aug 11 – 18

G$22,787 GYD per night

Guest favorite

Home in Milwaukie

4.96 out of 5 average rating, 133 reviews

Crossroads Country Cottage

Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

Jan 13 – 20

G$23,543 GYD per night

Guest favorite

Tiny home in Damascus

4.92 out of 5 average rating, 638 reviews

Quaint Tiny House In The Trees. Damascus, Oregon.

Tiny House In The Trees (must leave message upon booking & 2 hour notice before arriving). A 150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to Portland, One hour or less to the mountain, 40 min to waterfalls in the Columbia Gorge. Located in Damascus Oregon. Pool open in the summer season only.

Dec 11 – 18

G$12,350 GYD per night

Guest favorite

Guesthouse in Portland

4.97 out of 5 average rating, 388 reviews

Moss Rock Retreat - Near Leach Botanical Garden!

Moss Rock Retreat is a peaceful tiny home surrounded by an acre of hillside gardens. Tucked behind the magical Leach Botanical Garden in a forested neighborhood, Moss Rock has the serenity of a mountain retreat - but is only 20 minutes from downtown and PDX. Come for respite from the busy world, a quiet workspace, a creative getaway, a romantic weekend, or to explore the natural beauty of Oregon - all are possible in the comfortable intimacy of Moss Rock Retreat.

Oct 7 – 14

G$19,238 GYD per night

Guest favorite

Guest suite in Milwaukie

4.98 out of 5 average rating, 262 reviews

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

Oct 10 – 17

G$22,808 GYD per night

Guest favorite

Home in Damascus

4.89 out of 5 average rating, 102 reviews

Foxglove Farm Private Guest Suite

Enjoy a stay in a separate, ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

Sep 8 – 15

G$19,387 GYD per night

Guest favorite

Guest suite in Damascus

4.91 out of 5 average rating, 526 reviews

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests! Must leave a message when booking please and thank you.

Aug 25 – Sep 1

G$16,772 GYD per night

Guest favorite

Guesthouse in West Linn

4.93 out of 5 average rating, 340 reviews

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! COVID-19 UPDATE: For Social Distancing get togethers, there is a cozy, covered, and private 12' x 11' outdoor space attached to the cottage, with lights. 4 or 5 people could easily sit over 6 feet apart.

Feb 20 – 27

G$17,678 GYD per night

Guest favorite

Apartment in Milwaukie

4.99 out of 5 average rating, 153 reviews

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Oct 19 – 26

G$19,058 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Happy Valley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Happy Valley's top sights

Happy Valley Station food carts27 locals recommend

Happy Valley Park10 locals recommend

New Seasons Market31 locals recommend

Carver Hangar10 locals recommend

Kaiser Permanente Sunnyside Medical Center3 locals recommend

Dean's Homestyle Cafe5 locals recommend

Other great vacation rentals in Happy Valley

Guest favorite

Guest suite in Oregon City

4.95 out of 5 average rating, 190 reviews

Farm Charm: 1000sq ft private studio in rural area

Dec 17 – 24

G$23,809 GYD per night

Guest favorite

Guesthouse in Beavercreek

5.0 out of 5 average rating, 143 reviews

Muse Cabin in old growth forest w/cedar hot tub

Sep 22 – 29

G$24,501 GYD per night

Guest favorite

Vacation home in Oregon City

4.93 out of 5 average rating, 461 reviews

Sunday Quiet, awesome Hood view, hot tub!

Sep 22 – 29

G$18,495 GYD per night

Guest favorite

Guesthouse in Boring

4.94 out of 5 average rating, 144 reviews

Boring Bungalow / Mt Retreat

Oct 22 – 29

G$21,686 GYD per night

Guest favorite

Guest suite in Oregon City

4.95 out of 5 average rating, 435 reviews

Master Suite Overlooking Clackamas River!

Sep 13 – 20

G$15,082 GYD per night

Guest favorite

Bungalow in Gladstone

4.94 out of 5 average rating, 118 reviews

The Wee Humble Cottage

Sep 21 – 28

G$22,318 GYD per night

Guest favorite

Guest suite in Troutdale

4.94 out of 5 average rating, 191 reviews

Upscale Troutdale Apartment Near The Edge!

Feb 25 – Mar 4

G$15,358 GYD per night

Guest favorite

Guest suite in Boring

4.95 out of 5 average rating, 407 reviews

Tiny Private Studio near Sandy, Oregon

Sep 5 – 12

G$17,410 GYD per night

Show all

Quick stats about vacation rentals in Happy Valley

Total rentals
120 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
G$6,259 GYD before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Happy Valley?
Happy Valley has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Happy Valley?
Make yourself at home in Happy Valley by choosing from our most frequently booked neighborhoods. We have over 460 vacation rentals in Sunnyside, over 530 vacation rentals in Clackamas, and over 650 vacation rentals in Rock Creek.
Do house rentals in Happy Valley have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Happy Valley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Happy Valley have wifi?
Absolutely! We offer over 70 house rentals with wifi in Happy Valley. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Happy Valley have free parking?
Absolutely! We offer over 10 private suite rentals with free parking in Happy Valley. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Happy Valley?
Four-legged friends are welcome in Happy Valley. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in private suite rentals in Happy Valley?
Experience the best of Happy Valley with our private suite rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Private Suite Rentals in Happy Valley?
Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Happy Valley have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Happy Valley. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Happy Valley?
Yes! Work meets play with ease at over 60 vacation rentals in Happy Valley featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Happy Valley

Top-rated vacation rentals in Happy Valley

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Happy Valley vacation rentals

Stay near Happy Valley's top sights

Other great vacation rentals in Happy Valley

Guest suite in Oregon City

Guesthouse in Beavercreek

Vacation home in Oregon City

Guesthouse in Boring

Guest suite in Oregon City

Bungalow in Gladstone

Guest suite in Troutdale

Guest suite in Boring

Quick stats about vacation rentals in Happy Valley

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Happy Valley?

Where should I stay in Happy Valley?

Do house rentals in Happy Valley have a kitchen?

Do house rentals in Happy Valley have wifi?

Do private suite rentals in Happy Valley have free parking?

Are there pet-friendly vacation rentals in Happy Valley?

How much does it cost to stay in private suite rentals in Happy Valley?

What are the most popular amenities for Private Suite Rentals in Happy Valley?

Do house rentals in Happy Valley have air conditioning?

Are there vacation rentals with a dedicated workspace in Happy Valley?

Destinations to explore