The Best Vacation Rentals to Book in Oregon

Come home to a spacious vacation rental for ultimate relaxation after a busy day exploring Oregon
Come home to a spacious vacation rental for ultimate relaxation after a busy day exploring Oregon | Courtesy of Hwy 126-Cooper / Expedia
Photo of Dave Stamboulis
16 December 2021
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Oregon is home to some of the most diverse scenery in America, from rugged windswept coastline to evergreen forests, snowclad volcanoes and even sun-drenched high desert. To make the most of your visit, stay at one of the best vacation rentals in Oregon, all bookable with Culture Trip.

Rocky Mountain 11, for outdoor adventures in Bend

Cosy double bedroom at Rocky Mountain 11 with tartan bed sheets, green and wooden walls and view of trees
Courtesy of Rocky Mountain 11 / Expedia
Bend is the adventure capital of Oregon, home to deep powder in the winter and plenty of high desert beauty in the summer. At this quiet retreat, you’ve got four bedrooms that can sleep up to 10 people, and you’re just minutes away from hiking, boating and all the aquatic activities along the Deschutes River, eastern Oregon’s top attraction. Fort Rock Park and the Sunriver Nature and Sunriver Aquatic centers are also within walking distance.

Wildflower Condo #44 by Village Properties at Sunriver, for a nature escape in Bend

Homely living room at Wildflower Condo #44 with wooden ceiling, balcony and leather sofa
Courtesy of Wildflower Condo #44 by Village Properties at Sunriver / Expedia
This nifty, wood-clad cabin gives you access to Mt Bachelor Ski Resort and Sunriver Golf Course in Bend, as well as the nearby Sunriver Recreation Center and the unique Lava Cave. The two-level condo features a spacious kitchen and country lodge-style furniture and decor, plus there is a fitness center, tennis court and library available to guests at the adjoining Sunriver Resort.

Hwy 126-Cooper, for big group getaways in Sisters

Simple but elegant double bedroom at Hwy 126-Cooper with monochrome colour palette and wire frame bed
Courtesy of Hwy 126-Cooper / Expedia
You’ll have everything you could possibly need at this vast, 20-acre (8ha) holiday home set amid the pines. Complete with five bedrooms, two ponds, a greenhouse and a hot tub, the property sleeps up to 20 people. Bring your whole family or school group, and explore all the nearby attractions like rock climbing at Smith Rock State Park, hiking in the Cascades or exploring charming little Sisters, just 4mi (6.4km) down the road.

The Neahkahnie House, for beachfront activities in Manzanita

Exterior of The Neahkahnie House with parking space and trees in the background
Courtesy of The Neahkahnie House / Expedia
This immaculate house set on Manzanita Beach looks out to both the ocean and Neahkahnie Mountain. When you’re not out tidepooling or beachcombing, you’ll love sitting in the Finlandia sauna or five-person hot tub, playing ping pong in the garage, letting the kids play football or games in the arcade room, or barbecuing out on the spacious deck. This is one fully equipped rental in an unbeatable spot.

Sunset Edge of the Continent, for a stylish stay on the beach in Waldport

Large deck outside Sunset Edge of the Continent with jacuzzi and view of the beach
Courtesy of Sunset Edge of the Continent / Expedia
At this 3,000sqft (279sqm) home in Waldport, huge windows, vaulted ceilings and multiple decks – including one with a hot tub – enable you to drink in the fabulous ocean views. The two-level home has three bedrooms plus a bonus room with a sofa bed and a Murphy bed in the entry, should you want to bring extra guests along. You’re seconds from the sands of Wakonda Beach, and Newport is just 20 minutes down the road.

Blue Shutter Olivia Beach, for beachside city living in Lincoln City

Outdoor swimming pool at Blue Shutter Olivia Beach
Courtesy of Blue Shutter Olivia Beach / Expedia
Combine natural coastal beauty with city life at this modern beach cottage. Sleep upstairs in the two-bedroom suites and dine in the cozy nook downstairs, complete with a stainless steel gas range. The rest of the time, the sunken hot tub, exercise room and seasonal swimming pool will keep you occupied. With immediate access to the beach and park playground across the way, and shopping at Lincoln City Outlets less than five minutes’ drive away, you’ll never get bored.

Hope Floats, for a chic family vacation in Rockaway Beach

Double bedroom at Hope Floats with muted colour palette, large bed and white window shutters
Courtesy of Hope Floats / Expedia

This beautiful, three-bedroom, luxury home on Rockaway Beach comes with coffered ceilings, inset lighting, a farmhouse sink, an electric ceramic range and a patio with a fire pit set in woodlands right off the coast. One bedroom has a pair of bunk beds for the youngsters, while the master bedroom features a walk-in shower. Be sure to take the classic steam train ride that runs from Rockaway Beach down to Garibaldi along a scenic stretch of Oregon coast.

Colby’s Run, for unbeatable ocean vistas in Newport

Deck outside Colby’s Run with view of the ocean
Courtesy of Colby’s Run / Expedia
Settle into a hot tub overlooking the gorgeous expanse of Beverly Beach at this stunning three-bedroom home. It’s all about the scenery at Colby’s Run: the property has floor-to-ceiling, ocean-view windows looking all the way to Cape Foulweather to the north and Yaquina Head Lighthouse to the south. Even the kitchen sink overlooks the ocean, making dishwashing an inviting chore. Other distinct features include leather furnishings, a telescope and a fenced yard, so you can even bring your pets.

Mv28: Gold Beach Oceanfront Estate, for VIP luxury in Port Orford

Large open plan kitchen, dining, living room at Mv28- Gold Beach Oceanfront Estate with large wooden beams and view of the ocean
Courtesy of Mv28: Gold Beach Oceanfront Estate / Expedia
You’ll feel like royalty at this massive home estate. Sitting on 28 acres (11ha) of pristine oceanfront coastline, the grand, 10,000sqft (929sqm) property is built from Canadian old growth logs. The main house has four bedrooms and features a river rock fireplace and 35ft (10.6m) ceilings. Additionally, there is a gazebo, guesthouse, pond, two barns and even a private helipad for VIP access. This is Oregon luxury at its finest, and of course the pretty Ophir Beach is just a short walk away.

Sand Dollar Find, for a contemporary home amid the dunes in Pacific City

Living room at Sand Dollar Find with high ceilings, turquoise walls and grey sofas
Courtesy of Sand Dollar Find / Expedia

It’s not only sand dollars that you’ll find in lovely Pacific City. This contemporary three-bedroom home has a games room with ping pong and foosball tables, a loft with a futon sofa for your guests, a backyard hot tub and wood deck, a fireplace, a fully equipped kitchen and a Craftsman-style oak dining table. When you stay here, you’ll also enjoy walking access to miles of Pacific City beach, while the Pelican Pub down the road will take care of you when you don’t feel like cooking.

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