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Search results; Over 1,000 homes in Olive

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Top guest favourite
Cottage in Olive
Perch Cottages #7: Creek access + Sauna + Mt views
2 bedrooms, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.96 out of 5 average rating, 134 reviews
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Top guest favourite
Guest house in Olive
The Lily Cottage Guesthouse
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 182 reviews
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Guest favourite
Guest house in Olivebridge
The Ashokan Guest House
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 211 reviews
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Home in Shokan
15min to Phoenicia + Woodstock; Charming Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 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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Superhost
Home in Woodridge
Hotel Buyout | 54 Guests | Belvedere Suites
18 bedrooms, 45 beds, 18 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Home in West Shokan
Catskills Escape: Pool • Ski • Fire Pit • Chic
3 bedrooms, 4 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 70 reviews
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Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
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Guest favourite
Cabin in Olivebridge
Ravenscliff-Zen Mt. Retreat STR Permit # 22-10
5 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 73 reviews
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Top guest favourite
Cottage in Boiceville
The Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 239 reviews
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Top guest favourite
Home in Woodstock
Woodstock Catskills Retreat~Sweet, Private & Views
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 131 reviews
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Top guest favourite
Cabin in Shokan
Catskills 2 br Cottage
2 bedrooms, 5 beds, 1.5 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 52 reviews
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Guest favourite
Home in Olivebridge
Olive Woods House - Catskills Mountain Views
2 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 94 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
17–22 Sept
4.99 out of 5 average rating, 195 reviews
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Top guest favourite
Home in West Shokan
Mid-Century Retreat ‘POOL IS OPEN!’
2 bedrooms, 2 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Kingston
Mountain Rock: Privacy, BBQ, Firepit, Game Room
4 bedrooms, 6 beds, 4 bathrooms
9–14 Sept
4.94 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Kerhonkson
Modern Farmhouse by the Falls: Creek, Scenic Views
3 bedrooms, 4 beds, 3.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 68 reviews
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Guest favourite
Home in Olive
Perch Eagle House: Creek access + Sauna + Mt views
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 49 reviews
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Tiny home in Accord
Deer Hill Farm, fire pit, Sauna, Grateful Woods.
1 queen bed, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 178 reviews