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Search results; Over 1,000 homes in Olive

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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
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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
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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
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Top guest favourite
Home in West Shokan
Catskills Escape: Pool • Ski • Fire Pit • Chic
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 71 reviews
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Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 4 beds, 3.5 bathrooms
26 Sept – 1 Oct
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Top guest favourite
Cottage in Boiceville
The Cottage
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 249 reviews
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Home in Olivebridge
Country Getaway with Mountain View
3 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
4.99 out of 5 average rating, 80 reviews
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Guest favourite
Home in Shokan
15 min to Phoenicia +Woodstock; Stylish Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cabin in Boiceville
Winston's Place - Woodland Cozy Catskills Cabin
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Nov
4.98 out of 5 average rating, 579 reviews
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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
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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
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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
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Top guest favourite
Home in Olivebridge
High Point Meadows
3 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Accord
Architect-designed home, 10 acres, pool & hot tub
4 bedrooms, 4 king beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 56 reviews
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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
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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, 198 reviews
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Guest favourite
Barn in Kerhonkson
Barn Studio - Designer Loft, Projection
2 bedrooms, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Kingston
BRAND NEW! This New House Three
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 178 reviews
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Guest favourite
Cabin in Olivebridge
Ravenscliff-Zen Mt. Retreat STR Permit # 22-10
5 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 75 reviews