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Holiday houses in Happy Valley

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Quick stats about holiday rentals in Happy Valley

  • Total holiday rentals

    Explore 100 holiday rentals in Happy Valley

  • Nightly prices starting at

    Happy Valley holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,350 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Happy Valley holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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 holiday rentals in Happy Valley

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

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Top Guest favourite
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

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your a private pathway to a completely fenced, 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 Commute Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk, run or ride along Springwater Corridor.

4.95 out of 5 average rating, 123 reviews
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 Clackamas County

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

5.0 out of 5 average rating, 172 reviews
Guest favourite
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

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).

4.91 out of 5 average rating, 153 reviews
Top Guest favourite
A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.
Guesthouse in Clackamas

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

4.97 out of 5 average rating, 300 reviews
Top Guest favourite
A spacious living area features a light-colored leather sofa paired with a glass coffee table, complemented by an area rug. Natural light filters through large windows, illuminating the open layout that connects to the dining area and staircase in the background.
Home in Clackamas County

Home in Clackamas

Forget your worries in this spacious and serene space. Come stay at our beautiful home located in a peaceful neighborhood in Clackamas. With access to near by stores, food carts, mall, and many other essential locations that will fit your needs while you enjoy your stay in this beautiful 3 bedroom, stylish home! Please don't park your vehicle in the street on the fire lane, which is in front of the house. if you need additional parking, please park across from the house where its permitted.

4.99 out of 5 average rating, 100 reviews
Top Guest favourite
Apartment in Happy Valley

All the Views: Your Private Airbnb Near Portland

Guests tell us they love this view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, and has great wifi. • 750 square feet of privacy, including a large guest-only deck • Full kitchen, queen size bed and super 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

4.98 out of 5 average rating, 429 reviews
Top Guest favourite
A serene bedroom features a spacious bed adorned with an assortment of decorative pillows. Two modern bedside lamps flank the bed, providing soft light. A piece of abstract artwork hangs above the headboard, complemented by greenery on the side, creating a relaxing atmosphere.
Guesthouse in Happy Valley

Hygge House-luxurious secluded 3BR guesthouse

The Hygge House PNW is a place to unwind, get cozy and enjoy the company of those you love. Cuddle up with a cup of tea or a good book and enjoy a restful retreat. Enjoy country vibes while being moments away from Happy Valley City Center. Whether you're in town visiting friends and family or looking to experience everything Portland has to offer, the Hygge House has you covered. We hope you enjoy your time spent here and leave feeling relaxed and more connected with the ones you love.

4.9 out of 5 average rating, 187 reviews
Top Guest favourite
A spacious living area features large windows allowing natural light to fill the room. Comfortable dark gray sofas are arranged around a wooden coffee table. A television is mounted on the wall, and a potted plant adds a touch of greenery to the inviting space.
Home in Clackamas County

Rose Meadow Oasis

Bring the whole family to this freshly remodeled 1,300sqft, family-friendly haven! With plenty of room for fun and relaxation, this inviting space is perfect for creating lasting memories. Featuring 3 bedrooms, the open concept living is open and spacious! Located in a fantastic neighborhood, the home is walkable and close to parks, shopping areas, and other local attractions. Whether you’re looking for adventure or a quiet retreat, this is the perfect spot for your family’s getaway!

4.88 out of 5 average rating, 80 reviews
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

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.

5.0 out of 5 average rating, 125 reviews
Top Guest favourite
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

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.

4.96 out of 5 average rating, 109 reviews
Top Guest favourite
A spacious living room features comfortable seating arranged for relaxation. Natural light enters through large windows, illuminating the room. A wooden cabinet with decorative items is positioned against the wall, while a flat-screen TV is mounted above. Decorative lamps add warmth to the space.
Home in Happy Valley

Spotless, Spacious & Private 2 Bedroom Guest Suite

We’d like to welcome you to a spacious, completely separate 2 bedroom apartment featuring queen beds, large light and bright living room, a well equipped kitchen, laundry with full sized washer/dryer, work space, bath with walk-in shower, private patio with a great view for you to enjoy. You’ll feel right at home with this tastefully decorated and comfortable space. Fast WiFi, streaming services including Netflix, Prime Video and Disney+.

5.0 out of 5 average rating, 75 reviews
Top Guest favourite
Home in Damascus

Foxglove Farm Private Guest Suite

Enjoy a stay in a 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.

4.93 out of 5 average rating, 196 reviews

Popular amenities for Happy Valley holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Happy Valley's top sights

Clackamas Town Center

69 locals recommend

REI

52 locals recommend

Mount Talbert Nature Park

20 locals recommend

Happy Valley Park

18 locals recommend

North Clackamas Aquatic Park

17 locals recommend

Dave & Buster's

12 locals recommend

Other great holiday rentals in Happy Valley

Top Guest favourite
The exterior of a charming home is highlighted by well-manicured landscaping and vibrant yellow flowers in the foreground. The house features a welcoming entrance with stone accents and large windows, while a dark vehicle is parked in the driveway.
Home in Happy Valley

Stunning Ranch Home/Walkable Gorgeous Neighborhood

5.0 out of 5 average rating, 30 reviews
Top Guest favourite
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

Luxury one bed apartment-extended stay available

5.0 out of 5 average rating, 19 reviews
Guest favourite
A restful bedroom features a spacious bed with a soft white blanket, accompanied by two nightstands, each topped with a lamp. A large mirror reflects the serene atmosphere created by a mural of misty trees on the wall, enhancing the calming design.
Home in Happy Valley

Cozy Happy Valley Home - 20 Minutes to DT Portland

4.9 out of 5 average rating, 82 reviews
Top Guest favourite
Home in Gresham

Modern Home

4.99 out of 5 average rating, 72 reviews
Guest favourite
The spacious living room features a large, L-shaped sectional sofa, inviting relaxation. A minimalist coffee table sits at the center, adorned with decorative items. Natural light fills the room through multiple glass doors leading to a balcony, complemented by sheer white curtains and a potted plant in the corner.
Home in Damascus

The Big Cozy Family House

4.88 out of 5 average rating, 33 reviews
Top Guest favourite
Home in Happy Valley

Mt Scott Forest Retreat with Theater & Sauna

5.0 out of 5 average rating, 13 reviews
Top Guest favourite
Home in Happy Valley

Happy Valley Hideaway

4.91 out of 5 average rating, 66 reviews
Top Guest favourite
A modern farmhouse exterior is showcased, featuring a clean paved driveway leading to an inviting entrance. Lush green grass and well-maintained landscaping with shrubs and small trees surround the home, complemented by a clear blue sky.
Home in Damascus

Holly View Haven

4.98 out of 5 average rating, 53 reviews

When is the best time to visit Happy Valley?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$243 NZD$241 NZD$253 NZD$241 NZD$243 NZD$255 NZD$238 NZD$228 NZD$255 NZD$255 NZD$248 NZD$258 NZD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

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 20 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 60 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 70 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 70 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 70 house rentals with free parking in Happy Valley. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore