Vacation rentals in Clackamas County

Guesthouse in Oregon City

4.98 out of 5 average rating, 164 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

A black door with six panels is framed by light brown siding and is complemented by a matching welcome mat. A small outdoor light fixture is mounted above the door, and a doorbell is visible to the left.

Apartment 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!

4.75 out of 5 average rating, 442 reviews

An expansive green lawn is bordered by lush trees and shrubs, creating a serene outdoor space. Two dark wooden Adirondack chairs are positioned comfortably on the grass, inviting relaxation amid the natural surroundings.

Guest suite in Estacada

Country Living in a Forest Setting

Come stay in your own cozy, rustic mini apartment, a little over 25 minutes from the Portland suburbs, and about 45 minutes from downtown Portland. Our home sits on two wooded acres. You'll have a private deck, private bathroom, private entrance, and private living space. There is a queen bed in the bedroom and a futon/sofa in the living area that makes a twin-size bed. Check-in time is after 4 pm. Early check-in is possible, just contact us. No Smokers! One pet on approval, up to 45lbs.

Place to stay in Woodburn

4.91 out of 5 average rating, 253 reviews

A-Frame Cabin: Picturesque view and cozy interior

Minutes from the outlet mall, a peaceful and cozy A-Frame, nestled in the trees overlooking a rippling creek. The stairs to the loft lead to a room where there is a comfortable queen-size bed and television. The downstairs area has a fully-stocked kitchen, dining area and living area with lots of windows to enjoy the view. There is also patio with a table and chairs and propane grill where you can sit and enjoy the view of the pasture and water, with beautiful trees scattered about.

4.96 out of 5 average rating, 490 reviews

An outdoor seating area is surrounded by gravel, featuring four wooden Adirondack chairs arranged around a central space. Lush greenery and decorative stones are present, creating a natural and inviting atmosphere. The area is designed for relaxation amidst a quiet landscape.

Guest suite in Boring

Tiny Private Studio near Sandy, Oregon

Located between Mt. Hood and the Columbia Gorge! Cozy private studio, with a separate entrance on 2 quiet acres. This small studio has a comfortable queen bed with luxury linens throughout. A tiny kitchenette supplied with coffee, organic half and half, an assortment of tea, bottled water, and a few snacks. Wifi and YouTubeTV provided. Grocery stores, restaurants, movie theater, gym, and hiking trails just to name a few amenities all within 1 to 3 miles of our home.

4.91 out of 5 average rating, 463 reviews

A charming storybook cabin is framed by lush trees, adorned with hanging lights that warm the inviting facade. Flower boxes beneath the windows add color, while a pink door and decorative accents enhance the whimsical aesthetic. An ornamental fence encloses a neat garden area.

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!

4.97 out of 5 average rating, 170 reviews

A green lawn stretches across the foreground, bordered by a variety of flowering plants and shrubs. Large, leafy trees provide shade in the background, while decorative planters add color and texture to the landscape. The well-maintained garden area offers a sense of tranquility.

Apartment in Hubbard

Peace and Quiet on a Farm in the Country

Enjoy the peace and quiet of the country in a 2 bedroom apartment on a working berry farm. The apartment is located in a separate building away from the main house so there is lots of privacy as well. You can even pick your own marionberries and blueberries when in season. There are also a number of u-pick farms and farm stands in the area. When the restrictions for COVID-19 are lifted, you can be assured that the space will be thoroughly cleaned and disinfected.

4.99 out of 5 average rating, 393 reviews

A vibrant garden space is featured, with bright yellow flowers blooming abundantly in a lush planter. Two light green Adirondack chairs are positioned on a patio, inviting relaxation and enjoyment of the surrounding greenery.

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, 591 reviews

An air purifier is positioned on the floor with a minimalist white design featuring a circular top. The device is plugged in, with its cord visible on the tiled surface nearby. It is compact, contributing to the overall cleanliness and comfort of the space.

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.

Place to stay in Estacada

The kitchen area features wooden cabinetry and a sloped ceiling, creating a warm and rustic feel. A small window allows natural light to illuminate the countertop, which includes a coffee maker and stovetop. Organized kitchenware is stored on a nearby open shelf.

4.99 out of 5 average rating, 260 reviews

"Worth 10 stars" Lucky Dawg Hideaway

Our LUCKY DAWG Hideaway is a well-equipped unique comfortable space with a queen bed, small kitchen, laundry area and bathroom. The cozy outdoor patio adds to your living area. Estacada is centrally located (abt an hour drive) to both downtown Portland and Mt Hood for all-year skiing and world-class hiking...Plus, we're about a 2.5 hour drive to either the beach or the high desert of central Oregon...

4.96 out of 5 average rating, 291 reviews

A spacious studio room features a pool table with a green felt surface, positioned near a large window that allows natural light to enter. A queen-sized bed, adorned with a geometric quilt, offers comfortable sleeping arrangements. Decorative wooden furnishings complete the inviting atmosphere.

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.

A vintage windmill stands tall against a clear blue sky, surrounded by vibrant green foliage. The windmill's arm extends outward, with a weathered sign reading 'The Farm' attached, indicating its rustic charm.

5 out of 5 average rating, 107 reviews

Highland Park- secluded lodge near the city.

Fabulous lodge style home on 5 park-like acres with a small lake, outdoor fireplace, game room and tv room. Just 30 min from Portland and the airport. Sleeps 10. Main level; master with king bed and bath, one bedroom with twin beds, (can be converted to king), one bedroom with queen bed, two baths. Upstairs, one bedroom with king bed and bath, one room with queen hideabed, shared bath.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Clackamas County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Clackamas County

Guest favorite

4.93 out of 5 average rating, 46 reviews

Pet friendly & close to several wedding venues.

NickiRating, 5 stars1 week 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!

5 out of 5 average rating, 41 reviews

A well-equipped kitchenette features a Keurig coffee maker alongside an electric kettle. A selection of coffee pods is neatly organized in a drawer below. Tile backsplash adds texture to the warm wood cabinetry, complemented by under-cabinet lighting.

Home in Happy Valley

Spotless, Spacious & Private 2 Bedroom Guest Suite

BrianRating, 5 stars6 days ago

hands down the best Airbnb we've ever stayed at. it was truly spotless and it times you could hardly tell anyone had ever even used the space before. every amenity you could want and then some were provided and it was very easy to feel at home. we met Ted and Cindy and they are such great people and hosts that truly want your experience to be good. they go above and beyond and we can't say enough good things about our stay there. if I could give more than five stars I would. if we ever make it back to the Portland area we will absolutely try to stay at Ted and Cindy's place again. they really did think through every little detail and truly made our stay special.

A well-equipped kitchen is presented, featuring modern stainless steel appliances, including an oven and microwave. Light-colored cabinets are paired with a grey countertop and white subway tile backsplash. A door leads to a view of the outdoor area, allowing natural light to brighten the space.

5 out of 5 average rating, 3 reviews

Modern Cozy ADU in Oregon City

AngeloRating, 5 stars1 week ago

My wife and I originally booked at a nearby hotel but had to switch over to an Airbnb abruptly and Madisons listing was the nicest one we saw in the area. She was very responsive and accommodating late evening in the middle of the week which we appreciated. The place was exactly what we needed for the weekend as a couple in town for a wedding. Clean, roomy, fully equipped kitchen, comfy couch, bed and TV. Made our first stay in Oregon a memorable one!

5 out of 5 average rating, 30 reviews

Rural Country Home

KristianRating, 5 stars2 weeks ago

Really nice clean house with all the amenities super comfortable bedrooms, great kitchen and overall perfect for what we needed. Super quiet as well. Owners live on the other side of property so communication was easy Off the grid a little bit with a great old diner / bar in Redlands up the road 10 mins. About a 15 minute drive or so to Milo for some disc golf and a solid 15 minute drive or so to Oregon city. don’t expect a supermarket nearby and that’s what we loved about it. Tractors, farms, ranches, dodge 2500s and Christmas trees on the classic Oregon countryside. Would definitely book again on a return trip to Milo. 👍

Guest favorite

A neatly organized kitchen cabinet displays an assortment of mugs above a kettle and French press. Two wooden containers holding wooden stirrers and coffee supplies complete the setup, offering convenience for beverage preparation.

Guesthouse in Sandy

4.96 out of 5 average rating, 81 reviews

Come Escape @ Mount Hood Retreat

JamieRating, 5 stars2 days ago

We loved the view on the patio and the fireplace was very nice. The throws were a nice surprise and were very comfortable. The bed was very comfortable and the AC was amazing. The indoor fireplace was a nice touch. We really enjoyed staying here and highly recommend it to anyone looking for a secluded getaway with awesome views.

5 out of 5 average rating, 89 reviews

Guest suite in Sandy

Sandy Getaway by the River

FiRating, 5 stars1 month ago

I loved staying at Heidi and Ed's place. They were very thoughtful hosts who thought of all sorts of little things in the suite that would enhance the guest's stay. It was quiet and peaceful and I slept well. They provided very clear instructions to get there as Google maps was not accurate. My cell reception didn't really work there but their wifi worked very well. It was a lovely spot by the river. The place was also squeaky clean. I thought their check-out time was a typo but it's real! It was nice to not have to rush to leave. I will definitely stay again when I next come by the area. Thanks, Heidi and Ed!

Guest favorite

A serene landscape is depicted, featuring a gradient sky transitioning from soft orange to cool blue, with Mt. Hood visible in the distance. A mist envelops the grassy fields and trees, creating a tranquil atmosphere, indicative of early morning light.

Apartment in Oregon City

4.93 out of 5 average rating, 521 reviews

Sunday Quiet, awesome Hood view, hot tub!

SavannahRating, 5 stars1 week ago

Great relaxing place to stay. Truly enjoyed my stay. Beautiful patio to sit on in the morning sun with a great view of mt hood. David was so kind and responsive!