Holiday rentals in Oregon City

4.96 out of 5 average rating, 136 reviews

Guest house in West Linn

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.

Guest house in Oregon City

4.99 out of 5 average rating, 163 reviews

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Discover our serene Clackamas Riverfront Guest House – a peaceful riverside getaway. This stylish retreat features a private hot tub and sauna, blending modern comforts with rustic charm. Unwind by the fireplace, savor river views, and embrace nature's beauty. Our river facing backyard provides access to the river where you can fish for salmon, steelhead, go kayaking, rafting and enjoy water adventures. Perfect spot for romantic escapes or solo rejuvenation. Experience luxury nestled in nature.

4.99 out of 5 average rating, 104 reviews

Flat in Oregon City

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!

Shipping container in Oregon City

4.97 out of 5 average rating, 132 reviews

Sustainable Dream Container Getaway with a View

A private green-luxury container home inside a bamboo grove and lavender field overlooking a serene valley. This brand-new, single-level home features picture windows leading out to a quiet deck with sunset views every night. Situated in the heart of the Pacific Northwest between the mountain, lakes and coast - exploration, wine tasting and the best nature spots are just a short drive away. This private home can comfortably host couples or up to 3 people including the couch.

4.91 out of 5 average rating, 460 reviews

Farm stay in Oregon City

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

4.99 out of 5 average rating, 393 reviews

Guest suite in Milwaukie

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.

4.92 out of 5 average rating, 590 reviews

Guest suite in Damascus

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & 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. Can accommodate 3pm check in every day of the week except Tuesdays.

4.96 out of 5 average rating, 289 reviews

Farm stay in Oregon City

Farm Charm: 1000sq ft private studio in rural area

With unique vintage decor, this comfortable studio offers modern amenities in a peaceful country setting. The space has a private keypad entrance & 16 stairs (sorry, no elevator) to the guest studio attached to our home. Our friendly golden retriever Ollie will gladly greet you. Groceries & highway access are a mere 3 miles away. Portland is a short easy drive from our quiet country home.

4.95 out of 5 average rating, 406 reviews

Guest suite in West Linn

Evergreen Escape - Relaxing South Metro Studio

Recently updated pricing and NOW NO CLEANING FEES! Quiet basement studio with efficiency kitchen and full bath with rain shower. Located a short distance south of downtown Portland, West Linn is a quiet suburb on the Willamette River. Our home is walkable to a great pub, groceries and other restaurants. This listing includes a lofted queen bed with charming barn door for privacy.

4.99 out of 5 average rating, 258 reviews

Guest suite in West Linn

Private Casita in Historic Willamette

Located in the highly desired Historic Willamette district of West Linn, this newly-built casita provides a private bedroom and bathroom with its own entrance. Enjoy walking to restaurants, coffee shops, beer pubs, wine bars, and retail shopping all within several blocks, or take a stroll to the Willamette Park just six blocks south.

4.95 out of 5 average rating, 137 reviews

Tiny home in Oregon City

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.

4.96 out of 5 average rating, 112 reviews

Country Living Minutes from Town

You will have this entire, private home to yourself! This is a newer home at the end of a dead end street just outside the city limits of Oregon City. You can enjoy quiet evenings on the private patio and stargaze on those clear nights! You may even see a deer or two wander by.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Oregon City holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oregon City

4.99 out of 5 average rating, 94 reviews

Victorian Charm for Family or Bridal Getaway

JonathanRating, 5 starstoday

An absolutely gorgeous Victorian style house. Beautiful open floorplan with amazing event space. A large dining table for all your gathering's needs. Comfortable rooms with en-suite restrooms. And a full use kitchen for all our drink and snack needs. We rented the space as a family get-away as part of our trip to the Oregon Renaissance Faire. It was conveniently located in Oregon City, within walking distance of wonderful restaurants and a short drive to the Canby Fairgrounds. We could not have asked for a better place to stay. Rena, the host, was friendly, welcoming, and responsive to all our stay's needs. Thank you for the wonderful weekend!

4.96 out of 5 average rating, 72 reviews

Guest suite in Gladstone

Top of the World - Apartment near PDX w/ Fireplace

TrishaRating, 5 stars1 month ago

This was a very peaceful and comfortable stay. It was clean, relaxing, and the host was very responsive and accommodating. I have already planned a return trip.

4.93 out of 5 average rating, 45 reviews

Pet friendly & close to several wedding venues.

NickiRating, 5 stars1 day ago

The home was spacious, clean, and full of personality thanks to its fun and eclectic decor. We loved spending time on the back deck, enjoying the beautiful and peaceful surroundings. The house was well-stocked with all the essentials, and the beds were very comfortable. We had a great stay and would absolutely return!

Home in West Linn

5 out of 5 average rating, 4 reviews

A Harmony Retreat - Your Portland Wellness Stay

EmilyRating, 5 stars1 week ago

This place was perfect, Amazing location, Starbucks, 02 miles away. Easy freeway access, easy to find and get in and out. It was super clean and decorated so cute! A handwritten note, large towels and all the amenities, it was like we were at a luxury hotel! 100% would recommend

Superhost

Townhouse in Oregon City

4.75 out of 5 average rating, 91 reviews

"Blue Fern” in Historic Oregon City w/ BBQ grill

KareyRating, 5 stars2 weeks ago

Excellent accommodations! Had everything I needed, and it was in the perfect location! Had a wonderful time, and the linens were divine! Beds were comfortable and couldn't have asked for a more suitable place!

4.92 out of 5 average rating, 163 reviews

Bungalow in Gladstone

The Wee Humble Cottage

NaniRating, 5 stars1 month ago

Tracy was the best host - available for anything, but respectful of personal vacation time. The space was incredibly charming, and I am always so appreciative of hosts that welcome 4 legged ‘children’ with open arms… it can be hard to find! Look no further if you’re searching for a cozy home in a quaint, walkable location. I couldn’t have asked for a better stay!

4.95 out of 5 average rating, 55 reviews

Cute cozy 3 BDRM 2 Bath home in Oregon City Oregon

CreightonRating, 5 stars5 days ago

We very much enjoyed our stay. A very pleasant and comfortable house, in an appealing and quiet neighborhood. Our family stayed a week, and we'd be happy to stay again.