The 30 Best Holiday Rentals in Oregon

Ranked 1 out of 2,676 in the Oregon region, as well as being 1 of 16 for holiday rentals in Brookings.

• “Comfortable and inviting. Just like your own home!”
• “We will stay here next time we are in the area, loved everything about it!”
• “This place makes you feel comfortable and welcomed, we loved it so much.”
• See more reviews of Tanbark Shores Guest Suite

Ranked 2 out of 2,676 in the Oregon region, as well as being 1 of 38 for holiday rentals in Newport.

• “Idyllic stay with stunning beach views”
• “Absolutely a great escape. Thank you.”
• “Perfect anniversary”
• See more reviews of Starfish Point

Ranked 3 out of 2,676 in the Oregon region, as well as being 1 of 15 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 2,676 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 5 out of 2,676 in the Oregon region, as well as being 5 of 26 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 6 out of 2,676 in the Oregon region, as well as being 1 of 2 for holiday rentals in Terrebonne.

• “Exceeded expectations, will be staying again.”
• “Peaceful and nice view”
• “Very small”
• See more reviews of Crooked River Ranch Cabins

Ranked 7 out of 2,676 in the Oregon region, as well as being 1 of 94 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 8 out of 2,676 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 2,676 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 2,676 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 2,676 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 2,676 in the Oregon region, as well as being 3 of 41 for holiday rentals in Eugene.

• “Lovely place to stay”
• “Great place to stay”
• “I enjoyed it . Had to go to Oregon to get rid of my storage unit from when I lived there almost 3 years ago .”
• See more reviews of Contemporary 2-Bedroom Close to Downtown, Dining

Ranked 13 out of 2,676 in the Oregon region, as well as being 2 of 15 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 2,676 in the Oregon region, as well as being 5 of 41 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 2,676 in the Oregon region, as well as being 3 of 15 for holiday rentals in Portland.

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

Ranked 16 out of 2,676 in the Oregon region, as well as being 1 of 1 for holiday rentals in Dayton.

• “The lights are beautiful at night on the lane.”
• “Clean, fun, and vintage funky!”
• “So cute.”
• See more reviews of The Vintages Trailer Resort

Ranked 17 out of 2,676 in the Oregon region, as well as being 1 of 3 for holiday rentals in Silverton.

• “Quiet, spacious, bright with wonderful Mountain View.”
• “A very beautiful property and so comfortable!”
• “The apartment was immaculate!”
• See more reviews of Lovely Canyon View Apartment with Patio and Yard

Ranked 18 out of 2,676 in the Oregon region, as well as being 2 of 8 for holiday rentals in Newberg.

• “Great house for a family.”
• “There was a coffee pot but no coffee available”
• “This was a conveniently located, quiet getaway spot perfect for a wine tasting weekend.”
• See more reviews of Spectacular Valley View in Wine Country

Ranked 19 out of 2,676 in the Oregon region, as well as being 2 of 18 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 20 out of 2,676 in the Oregon region, as well as being 1 of 36 for holiday rentals in Sunriver.

• “We had a very nice family vacation.”
• “Great location and very spacious room!”
• “It was a great space to relax and enjoy Sunriver resort and the surrounding area.”
• See more reviews of The Pines at Sunriver

Ranked 21 out of 2,676 in the Oregon region, as well as being 4 of 15 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 2,676 in the Oregon region, as well as being 8 of 41 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 23 out of 2,676 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 2,676 in the Oregon region, as well as being 2 of 94 for holiday rentals in Seaside.

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

Ranked 25 out of 2,676 in the Oregon region, as well as being 1 of 9 for holiday rentals in Medford.

• “The owners communication with me always accommodating my...”
• “The little things”
• “The room was so cozy and comfortable.”
• See more reviews of Oakdale Suites - Master Property

Ranked 26 out of 2,676 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 27 out of 2,676 in the Oregon region, as well as being 4 of 22 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 28 out of 2,676 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 29 out of 2,676 in the Oregon region, as well as being 2 of 51 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

Ranked 30 out of 2,676 in the Oregon region, as well as being 3 of 51 for holiday rentals in Rockaway Beach.

• “Excellent stay at Rockaway”
• “Very happy with our stay. Would not hesitate to stay again.”
• “The location was perfect!”
• See more reviews of Rockaway beach vibes,Waterfront Oceanfront Rockaway Beach House near Downtown,WIFI, Washer Dryer