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Holiday houses in Oregon City

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Quick stats about holiday rentals in Oregon City

  • Total holiday rentals

    Explore 130 holiday rentals in Oregon City

  • Nightly prices starting at

    Oregon City holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 8,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Oregon City holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oregon City rentals

  • 4.8 Average rating

    Oregon City stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Oregon City

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.
Guesthouse in West Linn
4.97 out of 5 average rating, 184 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
Apartment in Oregon City
4.99 out of 5 average rating, 151 reviews

Private, comfy & cozy apartment in OC neighborhood

Enjoy a comfortable stay in our private (above garage) apartment. Safe, quiet and family friendly neighborhood with walkable distance to 2 parks. 10 minutes to the I-205 freeway and 25 min to PDX airport. Within 2 hours of the coast or Mt. Hood. Oregon City has several fun things to offer near by :: Food trucks, restaurants, brew pubs, shopping, coffee shops, free OC elevator with amazing views, End of the Oregon Trail museum, walking trails, Clackamas and Willamette rivers and so much more!

Top Guest favourite
The exterior showcases a charming white house with a grey door and surrounding landscaping. Leafy trees frame the entrance, and a fenced area provides privacy. A pathway leads to the entry, complemented by a well-maintained yard and a concrete driveway.
Home in Oregon City
5.0 out of 5 average rating, 39 reviews

Bright & Airy Cottage

Relax in this beautifully updated 2-bedroom + bonus room home in a walkable Oregon City neighborhood. Blending historic charm with modern comforts, it sleeps up to 8, perfect for professionals, couples, or families. Enjoy easy access to dining, shopping, parks, the library, and Willamette Falls Medical Center. Unwind in spacious living areas, or cook in the fully stocked kitchen. The huge bonus room is perfect for additional guests. Experience the best of Oregon City from this inviting retreat.

Superhost
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
4.97 out of 5 average rating, 296 reviews

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!!

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
5.0 out of 5 average rating, 169 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
A well-maintained path leads to the entrance of the cottage, surrounded by lush greenery and vibrant flowering shrubs. The rustic exterior is complemented by a sunlit porch, offering a welcoming entryway into a tranquil outdoor space.
Cottage in West Linn
4.87 out of 5 average rating, 206 reviews

The Bee Cottage

Welcome to The Bee Cottage! This cozy cottage is nestled in the woods overlooking a beautiful sun-filled meadow situated on 5 private acres adjacent to Mary S. Young Park. In this quiet and pastoral setting you'll see deer wandering in the orchard and on the other side of the meadow are honeybee hives tended to by the host. It’s a separate home with a fully stocked kitchen, an outdoor deck and barbecue great for entertaining just 3 blocks from Cedar Oaks Park/Boat Ramp on the Willamette River.

Top Guest favourite
A welcoming front porch is presented, featuring warm wood siding and a secure wooden door. A comfortable chair and small table are positioned on the polished wooden floor, surrounded by lush greenery visible in the background.
Home in Gladstone
4.96 out of 5 average rating, 157 reviews

Gladstone Garden Retreat

Lovely updated bungalow, private & quiet garden retreat in old Gladstone home, walking distance to Clackamas River. Gated yard with garden, grill, outdoor dining, east facing windows, private keyless entrance, off street parking. Tons of natural light; beautifully decorated; AC, HDTV, Wi-Fi, Cable TV with movie channels; Queen beds; designer appliances for gourmet meals; rock fireplace w/ gas, soaking tub upstairs, updated shower downstairs; washer & dryer. Pet friendly patio w/ doggie door.

Top Guest favourite
A modern green-luxury container home is set amidst a lush bamboo grove with soft landscape lighting. Large windows provide a view into the interior, while a quiet deck is accessible from the home, surrounded by natural greenery and a serene sunset backdrop.
Apartment in Oregon City
4.98 out of 5 average rating, 205 reviews

Bamboo & Lavender Luxury Container Retreat w/ View

Tucked inside a private bamboo grove and lavender field, Black Box Retreat is a brand-new luxury container home with sweeping valley views. Watch hummingbirds nest in the bamboo, deer graze at dusk, and sunsets turn golden from your private deck and fire pit. Inside, enjoy luxury finishes, room-darkening shades, a full kitchen, and dedicated workspace — perfect for couples, solo travelers, or groups of up to 3. World-class hiking, wineries, and the Oregon coast are just a short drive away.

Guest favourite
A charming blue cottage is framed by a welcoming front porch with wooden railings. Lush green plants and purple flowers decorate the landscape. An American flag is displayed on the railing, and a car is parked in the driveway alongside the property.
Bungalow in Gladstone
4.91 out of 5 average rating, 197 reviews

The Wee Humble Cottage

Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

Guest favourite
Home in West Linn
4.89 out of 5 average rating, 103 reviews

2.3k sqft Cozy Kid Friendly+ playground Toys Gym

The 2.3k sqft private space on the lower level of our home features a separate entrance and large windows with scenic views of greenery. Our family, including young children, lives upstairs, and we’ve added extra soundproofing for your comfort. You may occasionally hear faint footsteps or muted conversations during the day. The space is designed to be family-friendly, with fun activities for kids to enjoy. We appreciate your understanding and look forward to hosting you!

Superhost
Home in West Linn
5.0 out of 5 average rating, 41 reviews

Historic RiverPlace West Linn

Historic West Linn Riverside Retreat: Modern Comfort Meets Stunning Views Welcome to your perfect getaway! This beautifully renovated home offers breathtaking river views and a prime location just minutes from downtown Oregon City. Nestled on a quiet, secluded street, this West Linn gem provides the best of both worlds—peaceful suburban charm with easy access to vibrant city life. Book your stay and experience the beauty, comfort, and adventure of riverfront living!

Top Guest favourite
Home in Canby
4.96 out of 5 average rating, 103 reviews

Newly updated home fully fenced yard and privacy!

Enjoy a peaceful stay at a centrally-located home! Newly remodeled home with stylish furnishings are ready for you to enjoy a lovely space. Comfortable beds will assure a good night’s sleep. A covered patio to enjoy the outside. This lovely home is centrally located between the I-5 and I-205 freeways, but located in a small friendly town. The river is only 3 blocks away! A very walkable town with many resturants close by. Come and enjoy!

Popular amenities for Oregon City holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Oregon City's top sights

Willamette Falls

52 locals recommend

End of the Trail Interpretive Center

51 locals recommend

Oregon City Brewing Company

30 locals recommend

Oregon City Municipal Elevator

28 locals recommend

Mary S. Young Park

21 locals recommend

eNRG Kayaking

19 locals recommend

Other great holiday rentals in Oregon City

Superhost
A cozy living area features two brown leather chairs positioned across from a wooden coffee table, adorned with books and a small vase of flowers. A large, vibrant floral rug adds color to the space, while sliding glass doors open to a deck with outdoor seating.
Home in Oregon City
4.95 out of 5 average rating, 85 reviews

Stunning View Near Top Wedding Venues-Pet Friendly

Top Guest favourite
A bright entryway features a white front door with glass inserts, framed by light-colored walls. A round mirror is mounted above a small wooden table with a cushioned chair. Natural light enters through the door, enhancing the space's open feel.
Home in Oregon City
4.97 out of 5 average rating, 79 reviews

Modern Cozy ADU in Oregon City

Guest favourite
The living area features a modern black couch facing a wall-mounted flat-screen TV. A cozy electric fireplace is positioned below the television, creating a focal point. A wooden dining table with four high-backed chairs is situated beside a set of neatly arranged shelves.
Apartment in Oregon City
4.84 out of 5 average rating, 79 reviews

Oregon City Historic District Apartment

Guest favourite
The exterior of the garden house is presented, featuring a light-colored facade and a welcoming front door. Lush green grass surrounds the home, complemented by well-maintained flower beds with pink and purple plants. Soft, colorful clouds are visible in the sky above.
Home in Oregon City
4.93 out of 5 average rating, 40 reviews

Garden House

Superhost
Home in West Linn
5.0 out of 5 average rating, 4 reviews

The Cozy Corner Cottage

Top Guest favourite
An open gathering space features rustic wooden accents and a large picnic table at the center. A staircase leads to a second level, while the backdrop showcases various themed areas including a jail. Warm lighting highlights the charming interior.
Place to stay in Oregon City
4.98 out of 5 average rating, 98 reviews

End of the Oregon Trail Experience

Superhost
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
4.87 out of 5 average rating, 79 reviews

Rose Meadow Oasis

Superhost
Home in Oregon City
5.0 out of 5 average rating, 51 reviews

Rural Country Home

When is the best time to visit Oregon City?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$148 NZD$158 NZD$155 NZD$160 NZD$175 NZD$197 NZD$190 NZD$185 NZD$172 NZD$172 NZD$180 NZD$170 NZD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Oregon City?

    Oregon City has comfortable stays around its historic downtown, scenic riverside, and nearby residential neighborhoods. Many vacation rentals include family-friendly amenities, and options are available for larger groups or those traveling with pets.

  • What are the best things to do in Oregon City with kids?

    Families often explore Willamette Falls, hands-on exhibits at local museums, and nearby parks with playgrounds and walking trails. Seasonal farmer’s markets and community events welcome visitors of all ages.

  • What are some of the best things to do in Oregon City?

    Explore Willamette Falls, wander historic Main Street, and visit museums highlighting the Oregon Trail’s history. Outdoor parks around the riverfront and community markets are frequently suggested for a local experience.

  • How is the weather in Oregon City?

    Oregon City has cool, rainy winters around 36–47°F (2–9°C), and sunny, warmer summers between 58–82°F (15–28°C). Spring and fall bring mild temperatures and occasional showers, so a rain jacket and layers are useful year-round.

  • When is the best time to visit Oregon City?

    Late spring through early fall is often recommended for milder temperatures and fewer rainy days. Summer sees regional festivals, outdoor markets, and popular hiking opportunities.

  • What are the best places to visit in Oregon City?

    Visitors frequently explore the Oregon City Municipal Elevator, Willamette Falls, and the Museum of the Oregon Territory. Downtown’s historic Main Street and local parks make for popular stops.

  • What are some hiking trails in Oregon City?

    Enjoy walking or hiking at Clackamette Park or take in views at the Canemah Bluff Nature Park. Trails here are often tree-lined with river views and accessible paths suited for varied skill levels.

  • What are some family activities we can do in Oregon City?

    Explore interactive history at museums, stroll riverfront parks, and attend community markets or seasonal festivals. Many spots have playgrounds and open spaces for kids to enjoy.

  • What are some of the best day trip ideas from Oregon City?

    Day trips often include exploring Portland’s urban offerings, historic towns like Milwaukie, or hiking in nearby forests and waterfalls. Wine country and scenic drives through rural valleys are widely suggested for local flavor.

  • Are there any pet friendly accommodations available in Oregon City?

    There are pet-friendly stays throughout Oregon City, especially in residential areas and near riverfront parks. Vacation rentals often feature yards or easy access to walking trails for dogs.

  • What are some local tips for visiting Oregon City?

    Locals recommend comfortable shoes for walking the historic downtown and an umbrella or rain jacket, especially outside summer. Exploring the riverside, enjoying local markets, and chatting with shopkeepers can give insight into Oregon City’s community.

  • What is Oregon City known for?

    Oregon City is known for its Oregon Trail history, the distinctive Municipal Elevator, and Willamette Falls. The city has a vibrant riverfront, locally rooted museums, and strong ties to early western settlement.

  • What are the best hidden gems to explore in Oregon City?

    Explore Canemah Cemetery for quiet history, visit smaller neighborhood parks, or browse local artisan shops along Main Street. The city has unique public art installations and often hosts pop-up events.

  • What are the best foods to try in Oregon City?

    Sample Pacific Northwest flavors—locally sourced produce, fresh salmon, and hearty chowders—at downtown cafes and restaurants. Seasonal farmer’s markets and bakeries around the city are popular with residents.

  • What should I bring for a trip to Oregon City?

    Pack layers and a rain jacket, regardless of season, and comfortable walking shoes. If visiting local parks or markets, a reusable water bottle and small backpack make outings easier.

  • What is the nightlife in Oregon City like?

    Nightlife in Oregon City centers around casual bars, restaurants with live music, and small venues hosting performances. Some downtown spots feature locally brewed drinks and open mic nights.

  • What are the most popular events or festivals in Oregon City?

    Oregon City has community festivals in the warmer months, along with farmers markets that welcome locals and visitors throughout much of the year. Some events focus on local history, art, and seasonal celebrations.

  • Are there family friendly vacation rentals in Oregon City?

    Oregon City has many family-friendly vacation rentals, often in quiet neighborhoods or near parks. Rental homes typically provide extra space, kitchens, and easy access to popular family activities.

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