Holiday rentals near Crooked River Winery
We found 1,498 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Crooked River Winery that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
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Find the best place to stay - Crooked River Winery

SALT COTTAGE - Pet Friendly, Stylish Holiday Home - prime beach location
Sleeps 8 · 3 bedrooms · 1 bathroom
9.8 out of 10
exceptional
(108 reviews)
Top rated rentals - Crooked River Winery

Absolutely beautiful
10 out of 10
exceptional
(123 reviews)
Stunning location, nestled in the valley. 5 minutes to town. Massive rooms and plenty of space for activities inside and outside.
Melissa O.
Stayed July 2025
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value