The 30 Best Holiday Rentals in Oregon

Ranked 1 out of 2,729 in the Oregon region, as well as being 1 of 17 for holiday rentals in Brookings.

• “Great location with beautiful view of Pacific looking...”
• “Always good to get a good getaway and the view a very short walk away was a great bonus”
• “How clean, beautiful the suite and outside was.”
• See more reviews of Tanbark Shores Guest Suite

Ranked 2 out of 2,729 in the Oregon region, as well as being 1 of 42 for holiday rentals in Newport.

• “Can't wait to stay again”
• “Location, view”
• “Girls trip at the beach! Had the BEST hotel in Newport!”
• See more reviews of Starfish Point

Ranked 3 out of 2,729 in the Oregon region, as well as being 1 of 16 for holiday rentals in Portland.

• “Wonderful location near galleries and restaurants, extremely...”
• “Great value. Central to everything we needed to do. Would stay again”
• “Our home lost power and heat.”
• See more reviews of Duplex in Alberta Art District

Ranked 4 out of 2,729 in the Oregon region, as well as being 5 of 28 for holiday rentals in Ashland.

• “We really enjoyed our time here, everything was good!”
• “Beautiful place welcoming clean n comfy and a great...”
• “Quiet, private, immediately accessible parking.”
• See more reviews of Second Street Cottages

Ranked 5 out of 2,729 in the Oregon region, as well as being 1 of 2 for holiday rentals in Mount Hood Village.

• “Great place to stay, with fantastic interior decoration.”
• “Close to what we wanted to do”
• “Cool house in the trees and thoughtfully appointed, but smoke and dog hair were a bummer.”
• See more reviews of Cozy Bird house w Big screen!

Ranked 6 out of 2,729 in the Oregon region, as well as being 1 of 99 for holiday rentals in Seaside.

• “Clean, quiet and comfortable”
• “We were able to enjoy our visit in Seaside and home was secure and comfortable.”
• “Close to the main strip with all the shops.”
• See more reviews of RIVERWALK SEASIDE- Walk to beach, One level home, pet friendly

Ranked 7 out of 2,729 in the Oregon region, as well as being 1 of 2 for holiday rentals in Terrebonne.

• “Beautifully located cabin”
• “We stayed there so I could visit where I scattered my wife's ashes ten years ago.”
• “Spacious.”
• See more reviews of Crooked River Ranch Cabins

Ranked 8 out of 2,729 in the Oregon region, as well as being 2 of 21 for holiday rentals in Gold Beach.

• “Beautiful, safe, and comfortable place to stay with my family, we loved it here!”
• “Cozy family getaway”
• “Great time overall, nice property, nice owners.”
• See more reviews of Gold Beach Apartment with Activities - 2 Mi to Ocean

Ranked 9 out of 2,729 in the Oregon region, as well as being 4 of 16 for holiday rentals in Roseburg.

• “A great escape!”
• “What a pleasant surprise.”
• “Gladly will like to come back”
• See more reviews of The Double U Escape

Ranked 10 out of 2,729 in the Oregon region, as well as being 6 of 34 for holiday rentals in Cannon Beach.

• “This place was perfect for us to enjoy a quick trip to the beach!”
• “Great”
• “Great host, accommodations and location!”
• See more reviews of Cannon beach vibes, steps to the beach,WIFI,3 full bedroom en suites with 3 fireplaces,Near Downtown

Ranked 11 out of 2,729 in the Oregon region, as well as being 1 of 1 for holiday rentals in Myrtle Creek.

• “Very cute cottage.”
• “Nice get away The surrounding area was beautiful. Enjoyable to explore.”
• “I have stayed here several times, always clean and comfortable stay. Host are very accommodating and nice.”
• See more reviews of Charming, Private Cottage in Myrtle Creek

Ranked 12 out of 2,729 in the Oregon region, as well as being 2 of 43 for holiday rentals in Eugene.

• “Very clean”
• “Lovely place to stay”
• “Great place to stay”
• See more reviews of Contemporary 2-Bedroom Close to Downtown, Dining

Ranked 13 out of 2,729 in the Oregon region, as well as being 2 of 16 for holiday rentals in Portland.

• “Dougan Suites - It’s a home away from home”
• “Very comfortable accommodation. Would return next time we visit family in Portland.”
• “Great value and well-maintained”
• See more reviews of Dougan Suites

Ranked 14 out of 2,729 in the Oregon region, as well as being 5 of 43 for holiday rentals in Eugene.

• “Wonderful.”
• “Worked out fine”
• “Very convenient.”
• See more reviews of Welcome! Colorful 50's Ranch in the Heart of Eugene

Ranked 15 out of 2,729 in the Oregon region, as well as being 2 of 7 for holiday rentals in Newberg.

• “The proximity to Newberg was great.”
• “Really nice. Great for our family time at our daughter's graduation from George Fox Univ.”
• “Very family friendly!”
• See more reviews of Spectacular Valley View in Wine Country

Ranked 16 out of 2,729 in the Oregon region, as well as being 1 of 3 for holiday rentals in Silverton.

• “I would book it again in a heartbeat. A truely enjoyable experience.”
• “Extremely clean , spacious and beautiful”
• “Quiet, spacious, bright with wonderful Mountain View.”
• See more reviews of Lovely Canyon View Apartment with Patio and Yard

Ranked 17 out of 2,729 in the Oregon region, as well as being 1 of 1 for holiday rentals in Dayton.

• “Fun - Happy we tried it.”
• “As expected but the sleeping arrangements were awful”
• “Cute little spot”
• See more reviews of The Vintages Trailer Resort

Ranked 18 out of 2,729 in the Oregon region, as well as being 8 of 43 for holiday rentals in Eugene.

• “Very comfortable for our 3 nights in Eugene.”
• “Very nice rental”
• “The Pendleton was an excellent place to stay for our family with all of the amenities we needed.”
• See more reviews of THE PENDLETON

Ranked 19 out of 2,729 in the Oregon region, as well as being 3 of 16 for holiday rentals in Portland.

• “Lovely and private”
• “Very clean, comfortable and inviting. We had everything we needed. Comfortable bed, great bath/shower, and sitting”
• “Exceptional communication and hospitality from Art.”
• See more reviews of Boutique Style Apartment in the heart of SE

Ranked 20 out of 2,729 in the Oregon region, as well as being 1 of 35 for holiday rentals in Sunriver.

• “Always a fun, clean and comforting place to stay! We stay every year for our annual trip!”
• “We had a very nice family vacation.”
• “Great location and very spacious room!”
• See more reviews of The Pines at Sunriver

Ranked 21 out of 2,729 in the Oregon region, as well as being 4 of 16 for holiday rentals in Portland.

• “I understand this is an apartment in a home but with 9.9 ratings I thought it would be a bit quieter”
• “Lovely setting and very well appointed property.”
• “Great place to stay”
• See more reviews of Forest Park Sanctuary

Ranked 22 out of 2,729 in the Oregon region, as well as being 1 of 9 for holiday rentals in Medford.

• “Overall I enjoyed my stay and would book again.”
• “The owners communication with me always accommodating my...”
• “The little things”
• See more reviews of Oakdale Suites - Master Property

Ranked 23 out of 2,729 in the Oregon region, as well as being 4 of 22 for holiday rentals in Salem.

• “Super cute , easy to find and around everything!”
• “Great location in a clean, comfortable loft.”
• “Awesome place to spend a few days. Michael was attentive and professional. There’s a Mexican restaurant right down stree”
• See more reviews of Modern Upstairs Loft - Newly Renovated!

Ranked 24 out of 2,729 in the Oregon region, as well as being 2 of 99 for holiday rentals in Seaside.

• “Nice stay”
• “Would stay Again”
• “We loved the hotel, and Shane was so helpful, even came to show us how to light the fireplace”
• See more reviews of Lanai at the Cove

Ranked 25 out of 2,729 in the Oregon region, as well as being 2 of 19 for holiday rentals in McMinnville.

• “Would definitely recommend!”
• “We enjoyed our flat - the location was great and the flat was lovely.”
• “short and sweet.”
• See more reviews of 3rd Street Flats

Ranked 26 out of 2,729 in the Oregon region, as well as being 3 of 23 for holiday rentals in Bandon.

• “Cypress Haven in Bandon, OR”
• “Everything is very good.”
• “It's a lovely light filled space with charming decor and...”
• See more reviews of Driftwood Duet

Ranked 27 out of 2,729 in the Oregon region, as well as being 3 of 99 for holiday rentals in Seaside.

• “Love this place - near all, comfy”
• “It was ok”
• “Hot tub”
• See more reviews of WorldMark Seaside by BookTimeShares

Ranked 28 out of 2,729 in the Oregon region, as well as being 1 of 1 for holiday rentals in Forfar.

• “Relaxing mini vacation”
• “Easy access to the beach.”
• “The cabin was great and very nice.”
• See more reviews of Whalers Rest

Ranked 29 out of 2,729 in the Oregon region, as well as being 2 of 2 for holiday rentals in Mount Hood Village.

• “Thank you for having us as guests & allowing a late check-in, thanks!”
• “Great location and proximity to Mt Hood”
• “I would stay there again. Over all we had a nice stay”
• See more reviews of SKI-Mount Hood Charm-Welches,Golf and SKI resort condo,W&D, WIFI,Near Woods,Hiking,Fishing

Ranked 30 out of 2,729 in the Oregon region, as well as being 2 of 55 for holiday rentals in Rockaway Beach.

• “Absolutely perfect.”
• “Wouldn’t book again”
• “It was a beautiful condo and an awesome vacation 😊”
• See more reviews of Rockaway oceanview condo,Steps to the beach & Downtown,W&D, WiFi