Bear Crossing holiday rentals
We found 216 holiday rentals — enter your dates for availability
Discover a selection of 18 homes and other holiday rentals in Bear Crossing that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as air conditioning and Wi-Fi. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.
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Find the best place to stay - Bear Crossing

5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
Sleeps 16 · 5 bedrooms · 3+ bathrooms
10 out of 10
exceptional
(225 reviews)
Top rated rentals - Bear Crossing

A Fabulous White Christmas at Winter Park
10 out of 10
exceptional
(163 reviews)
At four weeks we had longish stay at Bob's condo and thoroughly enjoyed every aspect of our Christmas holiday. The condo is well situated to take advantage of the frequent buses to the ski area. We rented a ski locker at Winter Park so the whole skiing experience was most convenient. Bob takes very seriously the comfort and well being of his guests, which we appreciated. We hope to be able to return soon.
D. Stuart P.
Stayed Dec 2018
- 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