Discover a selection of 59 homes, 12 apartments and other holiday rentals in Winthrop that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as air conditioning and a pool. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
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Explore Winthrop cabin rentals

Little Bear Cabin-Dog Friendly, Close to Winthrop's Downtown and Ski Trailhead!
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.8 out of 10
exceptional
(89 reviews)
Top rated cabin rentals - Winthrop

Quaint town
8.4 out of 10
very good
(1,689 reviews)
Very adequate for our one night stay. A bit dated but added to the charm.
Hardly anyone around at that time in the season with SR 20 only just opened.
Lots of deer just outside the town. Wifi no good in unit by river, but managed without it as the river views were awesome.
John
Stayed Apr 2019
- 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





