Vacation rentals in Happy Valley

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Quick stats about vacation rentals in Happy Valley

  • Total vacation rentals

    Explore 110 vacation rentals in Happy Valley

  • Nightly prices starting at

    Happy Valley vacation rentals start at G$6,278 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Happy Valley vacation rentals include wi-fi 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!

Top-rated vacation rentals in Happy Valley

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

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Superhost
Home in Happy Valley
5 out of 5 average rating, 6 reviews

Cozy Happy Valley Cottage Retreat

Welcome to this charming three-bedroom cottage offering a peaceful stay in Happy Valley. The warm and inviting living space is perfect for relaxing after a day of exploring the Portland area. A nicely equipped kitchen makes it easy to prepare meals and gather around the table with family or friends. Each bedroom provides a comfortable and quiet retreat for restful nights. The third bedroom, to clarify, has a small futon that folds into a bed, best suited for kids. There is a full-sized bed (mattress only on the floor) as the main sleeping option in that space. This cottage combines cozy character with modern convenience for a relaxing Pacific Northwest getaway.

Top guest favorite
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.
Townhouse in Happy Valley
4.96 out of 5 average rating, 198 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. 15 mins to PDX, 25 mins Portland downtown and 50 mins to Mt Hood Gorge. 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 favorite
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.
Guesthouse in West Linn
4.97 out of 5 average rating, 176 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 favorite
A modern living area features a gray sectional sofa, positioned near large windows that invite natural light. A cozy, black gas fireplace adds warmth to the space, complemented by a round, textured pouf on the floor.
Guest suite in Gladstone
4.95 out of 5 average rating, 110 reviews

Top of the World - Apartment near PDX w/ AC

This relaxing, private suite is perfect for your stay! Our organized space includes high-speed wifi, a gas fireplace, and even a washer and dryer. The kitchen is fully equipped with a dishwasher, fridge, Nespresso coffee maker, hot plate, cookware, and a three-in-one microwave/air fryer/mini baking oven. You have your own entrance and the space to yourself. Guests find the location very convenient and we often hear that the space feels comfortable, homey, and that we've "thought of everything!"

Top guest favorite
A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.
Home in Milwaukie
4.96 out of 5 average rating, 114 reviews

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

Guest favorite
A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.
Home in Happy Valley
4.91 out of 5 average rating, 138 reviews

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

Top guest favorite
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 Clackamas
5 out of 5 average rating, 158 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

Top guest favorite
Apartment in Happy Valley
4.98 out of 5 average rating, 422 reviews

All the Views: A Private airbnb Near Portland!

Guests tell us they love this view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, with great wifi too. • 750 square feet of privacy, including the 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. Level 2 EV charger Clackamas County License #108 No children or infants, sorry.

Superhost
Home in Happy Valley
4.89 out of 5 average rating, 378 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 favorite
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
4.95 out of 5 average rating, 110 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 favorite
A spacious guestroom features a black bed with a yellow and gray throw blanket draped across it. A small dining table with black chairs is positioned nearby, while a large window offers natural light. Wall art and decorative plants add character to the space.
Guesthouse in Happy Valley
4.96 out of 5 average rating, 104 reviews

Modern Spacious Private Guesthouse!

This spacious guesthouse is the perfect spot to relax and unwind, located conveniently just a few minutes from an abundance of restaurants and stores. The home is equipped with a queen bed and futon, kitchenette, and dining area. For your convenience, you have your own washer and dryer in the unit. Explore stunning Oregon beauty by adventuring to the nearby parks and trails. If you'd rather cozy up inside, the guesthouse has free-wifi and Netflix.

Top guest favorite
A spacious bed dressed in a floral-patterned comforter is complemented by vibrant, textured pillows in various colors. Two stylish lamps with white shades provide soft lighting on either side, stationed on light wood nightstands featuring woven baskets.
Apartment in Happy Valley
5 out of 5 average rating, 15 reviews

Luxury one bed apartment-extended stay available

Looking for a great place to call home? You’ve found it! This stylish one-bedroom basement apartment is located in a quiet neighborhood and offers a perfect mix of comfort and privacy. Enjoy a modern kitchen with quartz counters, peninsula seating for four, and a butcher block coffee bar. Relax on your private deck by a tranquil water feature. Includes a leather sectional, TV, internet, a queen bedroom with en-suite, and in-unit washer/dryer.

Popular amenities for Happy Valley vacation rentals

When is the best time to visit Happy Valley?

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Avg. priceG$29,923 GYDG$29,714 GYDG$31,179 GYDG$26,157 GYDG$28,249 GYDG$26,994 GYDG$29,295 GYDG$28,040 GYDG$31,388 GYDG$31,388 GYDG$30,551 GYDG$31,806 GYD
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Frequently Asked Questions

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

    Happy Valley has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Happy Valley with our house 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.

  • 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.

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

    Yes! Work meets play with ease at over 70 vacation rentals in Happy Valley featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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.

  • Do house rentals in Happy Valley have a kitchen?

    Absolutely! We offer over 70 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 80 house 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 80 house rentals with free parking in Happy Valley. Enjoy a tailored experience with all the comforts you desire.

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