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Search results; Over 1,000 homes in Olive

Top guest favourite
Guest house in Olive
The Lily Cottage Guesthouse
1 bedroom, 1 bed, 1 private bathroom
8–13 Nov
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4.99 out of 5 average rating, 183 reviews
Top guest favourite
Home in Kerhonkson
Fall Farmhouse: Private, Firepit & Fireplace
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 191 reviews
Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 4 beds, 3.5 bathrooms
22–27 Sept
Top guest favourite
Home in Shokan
Historic Catskills farmhouse with sweeping views
4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Shokan
15 min to Phoenicia +Woodstock; Stylish Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Olivebridge
Catskills Hudson Valley Family Hideaway
3 bedrooms, 3 queen beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in West Shokan
Catskills Escape: Pool • Ski • Fire Pit • Chic
3 bedrooms, 4 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 71 reviews
Top guest favourite
Home in Olivebridge
Country Getaway with Mountain View
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Home in West Shokan
Mid-Century Retreat ‘POOL IS OPEN and steaming!
2 bedrooms, 2 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Stone Ridge
Poets, Dreamers and Lovers xo
5 bedrooms, 5 beds, 4 bathrooms
17–22 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Boiceville
The Cottage
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 246 reviews
Top guest favourite
Cabin in Shokan
Catskills 2 br Cottage
2 bedrooms, 5 beds, 1.5 bathrooms
10–15 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Chalet in Olivebridge
Spruced Moose Lodge & Treehouse w/ New Hot Tub!
4 bedrooms, 9 beds, 3.5 bathrooms
27 Oct – 1 Nov
4.99 out of 5 average rating, 197 reviews
Top guest favourite
Guest house in Olivebridge
The Ashokan Guest House
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.95 out of 5 average rating, 216 reviews
Top guest favourite
Cottage in Kerhonkson
Ye Little Wood | Cozy Forest Cottage with Hot Tub
2 bedrooms, 2 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 252 reviews
Guest favourite
Home in Olivebridge
High Point Mountain House ~ Summer on the Mtn!
5 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.94 out of 5 average rating, 119 reviews
Top guest favourite
Home in Shokan
<2 Hr NYC-Near Woodstock. New Reno. Amazing Views
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Olivebridge
Olive Woods House - Catskills Mountain Views
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Kerhonkson
Hudson Valley home with covered porch, fireplace
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.96 out of 5 average rating, 47 reviews