Oregon City vacation rentals

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Top-rated vacation rentals in Oregon City

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Guest favorite

Guest suite in Oregon City

4.95 out of 5 average rating, 435 reviews

Master Suite Overlooking Clackamas River!

Welcome to a beautiful view of the Clackamas River from our home in Oregon City! This is our Master Suite with it's own private entrance and deck. The Suite includes a bathroom/shower/tub, plants, a sitting area, king bed, mini fridge, microwave & Keurig. The suite shares a wall with our kitchen. Ask us about our expertise on the area! Chris is an outfitter and can set you up on a river float or a whitewater excursion. Carver is just minutes away, where scenes from Twilight were filmed.

Sep 14 – 21

G$15,082 GYD per night

Guest favorite

Apartment in Happy Valley

4.98 out of 5 average rating, 366 reviews

All the Views: Private AirBnB, near Portland!

Guests tell us they love the view! They also mention this downstairs apartment is really clean, spacious, comfortable and relaxing (even though the high speed WiFi is great for work). • 750 square feet of privacy with a private garage entrance • Full kitchen, queen size bed, blazing fast wifi • Leather furniture, large screen TV with HDMI capability (streaming only) • Private staircase leads to your garage entrance, with no shared spaces Level 2 EV charger (let us know ahead)

Jan 23 – 30

G$22,271 GYD per night

Guest favorite

Vacation home in Oregon City

4.93 out of 5 average rating, 461 reviews

Sunday Quiet, awesome Hood view, hot tub!

Welcome to our country home a mile to the Clackamas River, with panoramic view of Mt Hood from deck and hot tub. Advertised rate is for a private studio (queen bed) with its own entrance in the lower level of our two story home. You enter along a garden path onto private deck. Extra bedroom (king bed) is available only to guests staying in the studio for an additional $25/night per guest. (for all nights of the stay.) 14 mins to I-205, a mile to restaurants, 30 mins to airport (PDX).

Oct 29 – Nov 5

G$18,158 GYD per night

Guest favorite

Farm stay in Oregon City

4.94 out of 5 average rating, 352 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.

Apr 20 – 27

G$18,340 GYD per night

Guest favorite

Bungalow in Gladstone

4.94 out of 5 average rating, 118 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.

Oct 1 – 8

G$24,338 GYD per night

Guest favorite

Guest suite in Milwaukie

4.98 out of 5 average rating, 262 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.

Oct 10 – 17

G$22,808 GYD per night

Guest favorite

Guesthouse in Canby

4.95 out of 5 average rating, 184 reviews

Cozy Country Bungalow

*Cozy studio apartment on ten-acre farm. *One queen-size bed *Complete kitchen w/ range, dishwasher, microwave, refrigerator, toaster, and coffeemaker. *Large bathroom, sleeping area with queen bed, living/dining area, and washer and dryer access. *Wireless internet and wall-mounted 40" Smart TV with Netflix. *Relax on your private veranda, or go for a stroll on our 10 acre property. *Enjoy a picnic in the woods. Creek, pond, bridge, & view to enjoy.

Apr 28 – May 5

G$23,538 GYD per night

Guest favorite

Guesthouse in West Linn

4.93 out of 5 average rating, 340 reviews

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! COVID-19 UPDATE: For Social Distancing get togethers, there is a cozy, covered, and private 12' x 11' outdoor space attached to the cottage, with lights. 4 or 5 people could easily sit over 6 feet apart.

Feb 21 – 28

G$17,678 GYD per night

Guest favorite

Guest suite in Oregon City

4.95 out of 5 average rating, 190 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.

Nov 7 – 14

G$23,809 GYD per night

Guest favorite

Guest suite in West Linn

4.96 out of 5 average rating, 300 reviews

Studio in-law suite just south of PDX

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.

Jul 14 – 21

G$30,697 GYD per night

Guest favorite

Apartment in Milwaukie

4.99 out of 5 average rating, 153 reviews

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Aug 30 – Sep 6

G$19,058 GYD per night

Guest favorite

Cabin in Estacada

4.98 out of 5 average rating, 277 reviews

Creekside Cozy Cabin

Nestled among tall cedars, you'll find the Creekside Cozy Cabin a perfect place to relax and enjoy its calm surroundings. While there are neighbors on both sides of the cabin, you still get that country feel away from the city. We are 20 miles from PDX Airport and 21 miles from Downtown Portland, but the drive out to the cabin is worth every mile.

Oct 31 – Nov 7

G$29,221 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oregon City vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oregon City's top sights

Fred Meyer12 locals recommend

High Rocks Park10 locals recommend

The Highland Stillhouse31 locals recommend

McMenamins Oregon City17 locals recommend

Regal Hilltop Cinema10 locals recommend

Oregon City Municipal Elevator19 locals recommend

Other great vacation rentals in Oregon City

Guest favorite

Guesthouse in Gladstone

4.97 out of 5 average rating, 102 reviews

The River House - Waterfront Retreat w/Fireplace

Jan 18 – 25

G$38,517 GYD per night

Guest favorite

Guest suite in Milwaukie

4.95 out of 5 average rating, 151 reviews

Riverside Cottage Apartment.

Jan 19 – 26

G$25,634 GYD per night

Guest favorite

Guesthouse in Beavercreek

5.0 out of 5 average rating, 143 reviews

Muse Cabin in old growth forest w/cedar hot tub

Jul 26 – Aug 2

G$27,222 GYD per night

Guest favorite

Tiny home in Damascus

4.92 out of 5 average rating, 638 reviews

Quaint Tiny House In The Trees. Damascus, Oregon.

Jan 2 – 9

G$12,350 GYD per night

Superhost

Guesthouse in Milwaukie

4.86 out of 5 average rating, 152 reviews

Milwaukie Riverfront Guest House

Jul 18 – 25

G$37,530 GYD per night

Guest favorite

Guest suite in Milwaukie

4.96 out of 5 average rating, 376 reviews

River Forest Lake Apt w/hot tub. HOT find!

Oct 22 – 29

G$28,543 GYD per night

Guest favorite

Home in Milwaukie

4.96 out of 5 average rating, 133 reviews

Crossroads Country Cottage

Apr 5 – 12

G$23,543 GYD per night

Guest favorite

Guesthouse in Oregon City

4.91 out of 5 average rating, 185 reviews

Modern Tiny House | Near DT OC| Dual Shower Heads

Mar 6 – 13

G$36,320 GYD per night

Show all

Other great vacation rentals in Oregon City

Guest favorite

Place to stay in Brush Prairie

4.97 out of 5 average rating, 421 reviews

Spaceship Destination!

Jan 2 – 9

G$29,496 GYD per night

Guest favorite

Guest suite in Milwaukie

4.97 out of 5 average rating, 181 reviews

Trolley Trail Treasure in Oak Grove

Aug 21 – 28

G$23,781 GYD per night

Guest favorite

Cottage in Lake Oswego

4.93 out of 5 average rating, 227 reviews

Peacock Grove Cottage in Lake Oswego, OR

Oct 26 – Nov 2

G$16,485 GYD per night

Guest favorite

Guest suite in Troutdale

4.97 out of 5 average rating, 767 reviews

Amazing VIEW & Private Entry/Jetted Tub near Falls

Jan 23 – 30

G$27,551 GYD per night

Guest favorite

Place to stay in Woodburn

4.92 out of 5 average rating, 168 reviews

A-Frame Cabin: Picturesque view and cozy interior

Mar 7 – 14

G$21,639 GYD per night

Guest favorite

Guest suite in Damascus

4.91 out of 5 average rating, 526 reviews

Oasis Between City, River & Mountain. Damascus OR

Sep 16 – 23

G$15,105 GYD per night

Guest favorite

Guesthouse in Milwaukie

4.95 out of 5 average rating, 187 reviews

The Annex - Sunny, peaceful, modern and detached!

Oct 18 – 25

G$23,440 GYD per night

Guest favorite

Guest suite in Estacada

4.97 out of 5 average rating, 234 reviews

Countryside Private Guest Suite-Estacada Farmhouse

Oct 9 – 16

G$26,337 GYD per night

Show all

Quick stats about vacation rentals in Oregon City

Total rentals
120 properties
Wifi availability
110 properties include access to wifi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
5.7K reviews

Frequently Asked Questions

Where should I stay in Oregon City?
Make yourself at home in Oregon City by choosing from our most frequently booked neighborhoods. We have over 440 vacation rentals in Two Rivers, over 330 vacation rentals in Rosemont Summit, and over 160 vacation rentals in Rivercrest.
Are there vacation rentals with a dedicated workspace in Oregon City?
Yes! Work meets play with ease at over 80 vacation rentals in Oregon City featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oregon City?
Four-legged friends are welcome in Oregon City. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Oregon City?
Experience the best of Oregon City with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oregon City have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Oregon City. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Oregon City?
Oregon City has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Oregon City have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Oregon City. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oregon City have wireless internet?
Absolutely! We offer over 60 house rentals with wireless internet in Oregon City. Enjoy a tailored experience with all the comforts you desire.

Oregon City vacation rentals

Top-rated vacation rentals in Oregon City

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Oregon City vacation rentals

Stay near Oregon City's top sights

Other great vacation rentals in Oregon City

Guesthouse in Gladstone

Guest suite in Milwaukie

Guesthouse in Beavercreek

Tiny home in Damascus

Guesthouse in Milwaukie

Guest suite in Milwaukie

Home in Milwaukie

Guesthouse in Oregon City

Other great vacation rentals in Oregon City

Place to stay in Brush Prairie

Guest suite in Milwaukie

Cottage in Lake Oswego

Guest suite in Troutdale

Place to stay in Woodburn

Guest suite in Damascus

Guesthouse in Milwaukie

Guest suite in Estacada

Quick stats about vacation rentals in Oregon City

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Oregon City?

Are there vacation rentals with a dedicated workspace in Oregon City?

Are there pet-friendly vacation rentals in Oregon City?

How much does it cost to stay in apartment rentals in Oregon City?

Do house rentals in Oregon City have a bbq area?

Are there family-friendly house rentals in Oregon City?

Do house rentals in Oregon City have air conditioning?

Do house rentals in Oregon City have wireless internet?

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