The 29 Best Holiday Rentals in Oregon

Ranked 1 out of 2,964 in the Oregon region, as well as being 1 of 21 for holiday rentals in Brookings.

• “Everything was great 👍 the view was great 👍”
• “warm welcome by host, beautifully decorated and stunning view”
• “Extraordinary oasis in Brookings Oregon”
• See more reviews of Tanbark Shores Guest Suite

Ranked 2 out of 2,964 in the Oregon region, as well as being 1 of 48 for holiday rentals in Newport.

• “”
• “Perfect!”
• “The staff was amazing.the gentleman brought us cherries amd agate they also offer a nightly campfire with smores You c”
• See more reviews of Starfish Point

Ranked 3 out of 2,964 in the Oregon region, as well as being 1 of 73 for holiday rentals in Portland.

• “Quiet, relaxing home with comfortable beds will enhance your Portland experience.”
• “We loved our stay in Portland & will definitely book this property again!!”
• “Super clean and comfortable”
• See more reviews of Duplex in Alberta Art District

Ranked 4 out of 2,964 in the Oregon region, as well as being 1 of 10 for holiday rentals in Ashland.

• “The location was very convenient for walking to theaters restaurants and park”
• “Totally recommend!”
• “”
• See more reviews of Second Street Cottages

Ranked 5 out of 2,964 in the Oregon region, as well as being 3 of 18 for holiday rentals in Roseburg.

• “The cabin and location is very peaceful and relaxing which I don't experience even in a 4 or 5 star”
• “Relaxing & Beautiful”
• “”
• See more reviews of A Restful Studio Near a Creek and Forest - Pet Friendly

Ranked 6 out of 2,964 in the Oregon region, as well as being 1 of 3 for holiday rentals in Silverton.

• “”
• “The accommodations were wonderful!”
• “Great getaway, that was in a great location.”
• See more reviews of Lovely Canyon View Apartment with Patio and Yard

Ranked 7 out of 2,964 in the Oregon region, as well as being 2 of 22 for holiday rentals in Gold Beach.

• “”
• “Loved it felt like a home away from home perfect”
• “Relaxing stay”
• See more reviews of Gold Beach Apartment with Activities - 2 Mi to Ocean

Ranked 9 out of 2,964 in the Oregon region, as well as being 2 of 73 for holiday rentals in Portland.

• “A gem in Portland!”
• “Quiet neighborhood and free on street parking.”
• “Lovely escape”
• See more reviews of The Secret Garden

Ranked 10 out of 2,964 in the Oregon region, as well as being 1 of 25 for holiday rentals in Salem.

• “It was definitely lovely and would come back right away”
• “”
• “I would stay again if we needed a place out there and would recommend it to others.”
• See more reviews of Modern Upstairs Loft - Newly Renovated!

Ranked 11 out of 2,964 in the Oregon region, as well as being 1 of 6 for holiday rentals in Newberg.

• “The view was absolutely beautiful.”
• “the location was very nice great pet friendly space”
• “Wonderful!”
• See more reviews of Spectacular Valley View in Wine Country

Ranked 12 out of 2,964 in the Oregon region, as well as being 2 of 55 for holiday rentals in Eugene.

• “Lovely Place Close to All Eugene Has to Offer”
• “It was lovely, overall, and I’m really glad we found it!!”
• “Comfortable, clean, contemporary”
• See more reviews of Contemporary 2-Bedroom Close to Downtown, Dining

Ranked 13 out of 2,964 in the Oregon region, as well as being 1 of 1 for holiday rentals in Dayton.

• “Excellent customer service. Just close enough to town to feel like you have a getaway. I love it here.”
• “”
• “The charm, the amenities”
• See more reviews of The Vintages Trailer Resort

Ranked 14 out of 2,964 in the Oregon region, as well as being 3 of 73 for holiday rentals in Portland.

• “”
• “”
• “The location was close to Providence Medical Center.”
• See more reviews of Dougan Suites

Ranked 15 out of 2,964 in the Oregon region, as well as being 8 of 19 for holiday rentals in Cannon Beach.

• “Very spacious and convenient with each bedroom having its own bath facilities but could’ve been appointed better with al”
• “Great place we actually enjoyed it a lot with my family”
• “Would stay here again”
• See more reviews of Cannon beach vibes, steps to the beach,WIFI,3 full bedroom en suites with 3 fireplaces,Near Downtown

Ranked 16 out of 2,964 in the Oregon region, as well as being 3 of 55 for holiday rentals in Eugene.

• “great place to stay with family for Hayward track event”
• “Great location close to downtown!”
• “better heating throughout the house”
• See more reviews of Colorful 50's Ranch in the Heart of Eugene

Ranked 17 out of 2,964 in the Oregon region, as well as being 4 of 23 for holiday rentals in Grants Pass.

• “”
• “Wonderful place that made me wish we had longer to stay!”
• “Great find!”
• See more reviews of The River House

Ranked 18 out of 2,964 in the Oregon region, as well as being 2 of 10 for holiday rentals in Ashland.

• “Cotton sheets would make it a ten.”
• “”
• “nice place for 4 adults”
• See more reviews of The Mountain House by WanderLodges

Ranked 19 out of 2,964 in the Oregon region, as well as being 1 of 83 for holiday rentals in Rockaway Beach.

• “A nice getaway spot with friends.”
• “Nice but needs climate control.”
• “Beautiful ocean view.”
• See more reviews of Rockaway oceanview condo,Steps to the beach & Downtown,W&D, WiFi

Ranked 20 out of 2,964 in the Oregon region, as well as being 1 of 67 for holiday rentals in Seaside.

• “”
• “We had a great birthday celebration for my husband, with our children!”
• “Great”
• See more reviews of WorldMark Seaside by BookTimeShares

Ranked 21 out of 2,964 in the Oregon region, as well as being 4 of 73 for holiday rentals in Portland.

• “I had a great time. The house was clean and spacious, and the garden was beautiful.”
• “Lovely accommodation.”
• “Quaint, quiet respite”
• See more reviews of NE Portland Oregon Modern Victorian Duplex

Ranked 22 out of 2,964 in the Oregon region, as well as being 5 of 73 for holiday rentals in Portland.

• “Everything as described, easy check in process”
• “Amazing place, I like everything.”
• “Comfortable and convenient, met all of my needs.”
• See more reviews of Bright & Cozy Modern Studio, Fast WiFi, Quiet, Walkable to University of Portland

Ranked 23 out of 2,964 in the Oregon region, as well as being 6 of 55 for holiday rentals in Eugene.

• “Fabulous place to stay with family”
• “Perfect place for a family!”
• “Wonderful Stay!”
• See more reviews of THE PENDLETON - Walkable - Arcade Loft - Modern- Light & Bright

Ranked 24 out of 2,964 in the Oregon region, as well as being 6 of 73 for holiday rentals in Portland.

• “”
• “Comfortable and spacious apartment in convenient location.”
• “”
• See more reviews of Elegant Richmond Gem nestled up to Hawthorne Blvd.

Ranked 25 out of 2,964 in the Oregon region, as well as being 1 of 23 for holiday rentals in Bend.

• “This place is wonderful.”
• “Convenient & beautiful location, excellent communication...”
• “Would like to stay again!”
• See more reviews of Mt. Bachelor & Sun River Get Away

Ranked 26 out of 2,964 in the Oregon region, as well as being 1 of 2 for holiday rentals in Terrebonne.

• “Great”
• “It's beautiful here.”
• “First time in this area, will plan for a revisit.”
• See more reviews of Crooked River Ranch Cabins

Ranked 27 out of 2,964 in the Oregon region, as well as being 2 of 17 for holiday rentals in McMinnville.

• “”
• “Beautiful town, fantastic accommodation”
• “Will definitely recommend these apartments to friends because you have access to the lovely hotel Atticus.”
• See more reviews of 3rd Street Flats

Ranked 28 out of 2,964 in the Oregon region, as well as being 7 of 73 for holiday rentals in Portland.

• “Clean, cozy, private place in a quiet neighborhood”
• “”
• “”
• See more reviews of Little Henry House on Duke St

Ranked 29 out of 2,964 in the Oregon region, as well as being 3 of 83 for holiday rentals in Rockaway Beach.

• “We loved visiting Rockaway Beach and having the home be so close. We loved the house and the outdoor furnitureto sit in”
• “New construction ”
• “Peaceful”
• See more reviews of Lake Marie Lodge #32

Ranked 30 out of 2,964 in the Oregon region, as well as being 1 of 20 for holiday rentals in Government Camp.

• “We really enjoyed the unit. Had a great time would come back.”
• “Pool not working”
• “Cozy, clean, home vibe!”
• See more reviews of THE CLYDE - Your Cozy & Luxurious Mt Hood Retreat