Holiday rentals in Happy Valley

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Top-rated holiday rentals in Happy Valley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.
Guest house in West Linn
4.96 out of 5 average rating, 164 reviews

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

Top guest favourite
A spacious bedroom features a large bed with high-quality cotton bedding. A desk is positioned nearby, and a sliding door leads to an outdoor patio. Natural light brightens the room, highlighting a wall art piece depicting a cityscape.
Home in Sunnyside
4.96 out of 5 average rating, 179 reviews

1000+ sq private 2b1.5b unit in gated area

A private unit in gated resort like homesite centrally located. Kaiser hospital , Clackmas TC and Happy Valley TC are mins drive away. 25 mins to PDX, NW 23rd ave, Portland downtown and 50 mins to Mt Hood. Very quite and you can wake up to bird chirping in am. Evergreens provide nice soothing color year round. Patio and deck with dinning table give you chance to enjoy outdoor and sunset if weather permits. Full kitchen. Up to 1gb super fastinternet. Spacious for 4 no extra charges. Central a/c.

Top guest favourite
A modern bathroom is featured with a deep soaking tub and sleek wood vanity. A round mirror and stylish light fixtures provide illumination. Neutral-toned tiles add warmth to the space, while a small plant decorates the bathtub area.
Home in Richmond
4.9 out of 5 average rating, 105 reviews

Hawthorne House - A+ Location! Pet Friendly!

Killer location!! An ez 2 min walk down the street from Hawthorne/Division in SE Portland! Enjoy the best restaurants, shops, bars PDX offers! Centrally located in great neighborhood! Main floor unit w/private access! Self check in! Bright and airy living spaces! Fully equipped kitchen for preparing delicious meals. Full sized wash/dryer. High speed Wi-Fi. Cozy bedroom w/plush queen-sized bed. Clean and modern bathroom stocked w/essentials. I'm excited to host you during your visit to PDX!!

Top guest favourite
Flat in Richmond
4.87 out of 5 average rating, 478 reviews

Casa Mágica / Walk Everywhere!

Peaceful neighborhood, walk everywhere! Safety is our top priority. The Magic House is in the heart of Hawthorne's charming restaurant and boutique district: 3 blocks to SE Hawthorne & SE Division, 15 min to the airport, 10 min to Downtown and the Convention Center, 2 blocks to the Hawthorne Theatre. The 1909 Magic House was Todji's sculpture studio for 17 years, and we have done the restoration ourselves. We hope that you enjoy her unique character, up-cycled furnishings and artistry.

Top guest favourite
A single-level home is presented, featuring a light blue and gray exterior with a combination of brick and siding. The front yard is manicured with greenery, and a driveway leads to a two-car garage. A clear blue sky serves as the backdrop.
Home in Sunnyside
5 out of 5 average rating, 140 reviews

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

Guest favourite
Home in Sunnyside
4.9 out of 5 average rating, 366 reviews

Mid Century Villa w/Mountain View & Movie Theater

Just relisted as we had long-term renters due to total fire loss. 3400 sq ft hillside retreat decked out with rare furnishings. Take in the Cascade Mountains from the wraparound deck and lounge under giant maple trees. You'll love the 125” Hi-Def movie theater (w/ 200+ movies)! Two large primary suites with king bed and large showers. One additional queen bedroom and one large office. Close to urban and nature, 20min to the airport, with daytrip opportunities to all the PNW must-see spots.

Top guest favourite
A spacious living area features a large sectional sofa with patterned cushions, offering a comfortable place to relax. Natural light enters through sliding glass doors that lead to the outdoor space, while an adjacent dining area is visible, along with the kitchen in the background.
Guest suite in Happy Valley
5 out of 5 average rating, 123 reviews

Happy Valley - Serenity in the Suburbs

We offer you a spacious (1500 sq feet with 9 ft ceilings) daylight apartment which includes, 2 large bedrooms (one queen, two twins), full kitchen with basic supplies, full laundry, bathroom with shower, dining and living areas, office nook, covered outdoor patio for sitting, a secluded and quiet backyard great for birding, private parking spot and separate entry. Our property backs up to a protected nature area with a beautiful walking trail. Perfect for couples or a small family.

Top guest favourite
The exterior of the home is highlighted by a wooden facade with a metal roof. A wooden deck leads to the entrance, surrounded by lush greenery and well-maintained landscaping. Sunlight filters through the trees, illuminating the peaceful setting.
Cabin in Damascus
4.94 out of 5 average rating, 102 reviews

Cheerful 2 bedroom cabin on the Clackamas River

Take it easy at this unique and tranquil getaway. Nested on a bluff with sweeping territorial views bordered by the Clackamas River, this 2 bedroom home sits on an acre of property just outside of Portland. It has been completely updated with a new gourmet kitchen, spa-like bathroom, master with a private balcony, dedicated work space, and a huge deck to enjoy all that nature has to offer. The upper yard is fully fenced for your pup and there is private walking path to the river.

Top guest favourite
A sunlit sunroom features large windows overlooking greenery, creating a bright space. A dark cushioned seating area is positioned against the window, complemented by a rectangular table. A patterned rug adds texture to the warm wood floor, enhancing the room's inviting atmosphere.
Guest suite in Westmoreland
4.97 out of 5 average rating, 568 reviews

A sunny separate studio w/skylights

Your own modern large studio on 2nd floor with separate entrance, full kitchen, sunroom, skylights, 14-foot ceiling, balcony, desk, full bathroom, washer/dryer, dishwasher, gas stove, lots of windows. All this in a vibrant neighborhood, short walking distance to multiple coffee shops, restaurants, a single-screen movie theater, the light rail station, an open-late grocery store, a small park with a salmon run. One mile to Reed College, where Steve Jobs took a calligraphy class.

Top guest favourite
Flat in Happy Valley
4.98 out of 5 average rating, 416 reviews

All the Views: Your Private Getaway Near Portland!

Guests tell us they love the view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, with great wifi too! • 750 square feet of privacy, including a large private deck • Full kitchen, queen size bed and fast wifi • Leather furniture, large screen TV with HDMI capability (streaming only) • Private staircase leads to your garage entrance. No shared spaces. Garage entry. Level 2 EV charger Clackamas County License #108

Top guest favourite
The exterior of a garden studio is illuminated by string lights, creating a warm ambiance at night. An inviting patio features two wooden chairs and floral greenery, while blooming white flowers add a touch of natural beauty to the space.
Guest suite in Milwaukie
4.99 out of 5 average rating, 454 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.

Guest favourite
The entrance to the tiny house features a vibrant green door framed by natural wood, leading to a small porch area. A chair sits to the side, with lush greenery surrounding the property, enhancing the connection with nature.
Tiny home in Damascus
4.92 out of 5 average rating, 801 reviews

Quaint Tiny House In The Trees. Damascus, Oregon.

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 SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

Popular amenities for Happy Valley holiday rentals

When is the best time to visit Happy Valley?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Happy Valley?

    Happy Valley has more than 70 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 690 vacation rentals in Happy Valley, over 480 vacation rentals in Sunnyside, and over 550 vacation rentals in Clackamas.

  • Do house rentals in Happy Valley have a kitchen?

    Absolutely! We offer over 80 house rentals with a kitchen in Happy Valley. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Happy Valley have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Happy Valley. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Happy Valley have free parking?

    Absolutely! We offer over 90 house 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 30 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Happy Valley?

    Experience the best of Happy Valley with our apartment rentals, starting at about $60 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 Apartment Rentals in Happy Valley?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Happy Valley have air conditioning?

    Absolutely! We offer over 80 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 80 vacation rentals in Happy Valley featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about holiday rentals in Happy Valley

  • Total holiday rentals

    Explore 130 holiday rentals in Happy Valley

  • Nightly prices starting at

    Happy Valley holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 6,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Happy Valley holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Happy Valley rentals

  • 4.9 Average rating

    Happy Valley stays are highly rated by guests – averaging 4.9 out of 5!

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