Woodlands holiday lettings

We found 219 holiday rentals — enter your dates for availability

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March 2026

April 2026

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Find the best place to stay - Woodlands

Premier Host

Sunriver retreat; 5bed, 4primarysuite,Theatre rm!!

Sleeps 15 · 5 bedrooms · 5+ bathrooms

Spacious Indoor/Outdoor Living, Golf Course Frontage, Hot Tub, Bikes, Ping Pong

4 bedrooms · 3.5 bathrooms

Premier Host

5 Vine Maple - Gorgeous! Hot Tub, Theater Room, Golf Course, A/C, SHARC Passes, Bikes

Sleeps 16 · 6 bedrooms · 5+ bathrooms

Large Dog Friendly Home w/ Private Hot Tub, Golf Course Views, & SHARC Passes

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Incredible Sunriver Retreat, Pet Friendly, Next to Pool and Golf Course, Hot Tub, BBQ

Sleeps 8 · 3 bedrooms · 3 bathrooms

Top rated rentals - Woodlands

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Spring Break Escape! Sunriver Trails, Bike Paths, Rivers & Warm Fireplaces

Premier Host

Summer Oregon x London Family Trip

We really enjoyed our stay in Donna and Craig’s home. Communication in the lead-up and during our stay was excellent.They have truly thought of everything which meant we could really focus on spending our precious time with family. Thank you again so much! We’ll be back for sure!

MaryAnn B.

Stayed Aug 2024

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Enjoy full kitchens, pools, gardens and more
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