Holiday houses in Oregon City

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Top-rated holiday rentals in Oregon City

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Guest favourite

Guest suite in Oregon City

4.95 out of 5 average rating, 434 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.

26 Sept – 3 Oct

$853 AUD total

Guest favourite

Guesthouse in Beavercreek

5.0 out of 5 average rating, 141 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.

23 – 30 Oct

$1,315 AUD total

Guest favourite

Holiday 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).

4 – 11 Jan

$946 AUD total

Superhost

Guesthouse in Milwaukie

4.86 out of 5 average rating, 152 reviews

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

16 – 23 Oct

$1,889 AUD total

Guest favourite

Farm stay in Oregon City

4.94 out of 5 average rating, 351 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.

28 Aug – 4 Sept

$977 AUD total

Guest favourite

Bungalow in Gladstone

4.94 out of 5 average rating, 117 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.

3 – 10 Oct

$1,283 AUD total

Guest favourite

Guest suite in Milwaukie

4.95 out of 5 average rating, 151 reviews

Riverside Cottage Apartment.

Charming cottage apartment on a hill next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

3 – 10 Oct

$1,442 AUD total

Guest favourite

Guest suite in Milwaukie

4.98 out of 5 average rating, 260 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.

2 – 9 Oct

$1,243 AUD total

Guest favourite

Guesthouse in Canby

4.95 out of 5 average rating, 183 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.

7 – 14 Feb

$1,257 AUD total

Guest favourite

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.

25 Oct – 1 Nov

$967 AUD total

Guest favourite

Guest suite in Oregon City

4.95 out of 5 average rating, 189 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.

11 – 18 Sept

$1,225 AUD total

Guest favourite

Guest suite in West Linn

4.96 out of 5 average rating, 299 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.

2 – 9 July

$1,590 AUD total