Holiday rentals in Clackamas County

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Top-rated holiday rentals in Clackamas County

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Top guest favourite

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.

Top guest favourite

Flat in Oregon City

4.99 out of 5 average rating, 103 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!

Guest favourite

Guest house in Beavercreek

4.98 out of 5 average rating, 237 reviews

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautifully remodeled cabin that is heated exclusively by the wood stove, on the edge of an old growth cedar forest on our 11 acre farm/vineyard. Relax on the deck built into the trees, and sleep in the cozy loft with ladder, as you soak in the nature around you. The cabin has a mini kitchen for cooking. The cute out house is just across the path, and is seasonally shared with other hip campers. We have a hot/cold shower at the hot tub. The cedar hot tub is next to the garden.

Guest favourite

Farm stay in Oregon City

4.93 out of 5 average rating, 409 reviews

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

Top guest favourite

Guest suite in Boring

4.96 out of 5 average rating, 490 reviews

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.

Guest favourite

Yurt in Estacada

4.95 out of 5 average rating, 419 reviews

Forest island

Glamping at its finest !!!!!! Come enjoy our Private forest island retreat on our 22 acre working farm . Relax and take in the fresh air without the hassle of having to pack up all your camping equipment. The spacious yurt can accommodate up to 4 people with a queen size bed and a 2 person pull out cot. This private yurt is on a island on our land surrounded by the water and trees. We also have kayak for rental upon request to use at the surrounding lakes and river.

Top guest favourite

Guest suite in Milwaukie

4.99 out of 5 average rating, 393 reviews

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.

Guest favourite

Guest suite in Damascus

4.92 out of 5 average rating, 590 reviews

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.

Guest favourite

Tiny home in Damascus

4.92 out of 5 average rating, 747 reviews

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

Top guest favourite

Place to stay in Estacada

4.99 out of 5 average rating, 258 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...

Top guest favourite

Farm stay in Oregon City

4.96 out of 5 average rating, 288 reviews

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.

Guest favourite

Guest suite in West Linn

4.95 out of 5 average rating, 406 reviews

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.

Holiday rentals for every style

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Popular amenities for Clackamas County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Clackamas County

Top guest favourite

Tiny home in Estacada

5 out of 5 average rating, 50 reviews

Luxury Tiny Home with a view!

BrittanyRating, 5 stars1 week ago

Absolutely LOVED the Tiny Timber home! This place had amazing views, a great host and fully stocked with utilities, supplies and very clean home. This stay was magical! The hot tub was a huge plus after hiking all day!

Guest favourite

Flat in Damascus

4.91 out of 5 average rating, 79 reviews

Modern Townhouse

AlliRating, 5 stars1 month ago

Sara’s place was a great place to stay! Grocery store and gas very close by and was a private location. About 30 minutes from Portland area. There was no laundry detergent but sara was kind enough to drop some off on the doorstep so we could do our laundry the night before check out! She also let us check in which was much appreciated! Everything was very clean except the shower drain was a bit slow and the shower grout could use a good scrub but is an easy fix likely. Would also recommend bringing a pillow if you like more of a firm pillow. Air conditioning was great and worked well also! Thanks Sara!

Guest favourite

Guest house in Sandy

4.96 out of 5 average rating, 80 reviews

Come Escape @ Mount Hood Retreat

MikeRating, 5 stars1 day ago

We enjoyed a peaceful stay here. We felt the description was accurate to what we actually stayed in. The front porch is what we enjoyed the most. We felt the location was great to easily visit both the Columbia River and Mt. Hood areas.

Top guest favourite

Guest suite in Sandy

5 out of 5 average rating, 89 reviews

Sandy Getaway by the River

FiRating, 5 stars3 weeks 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 favourite

Flat in Oregon City

4.93 out of 5 average rating, 520 reviews

Sunday Quiet, awesome Hood view, hot tub!

SavannahRating, 5 starstoday

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!

Top guest favourite

Ranch in Sandy

4.95 out of 5 average rating, 87 reviews

Secluded mountain luxury home

BevanRating, 5 stars1 week ago

Don was fantastic, and the place was wonderful. We spent most of our time outside on the patio with a perfect view of Mount Hood, or inside in the theatre room. Great place and great host.

Top guest favourite