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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
20–25 Sept
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4.99 out of 5 average rating, 182 reviews
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Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 7 beds, 3.5 bathrooms
2–7 Sept
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Guest house in Olivebridge
The Ashokan Guest House
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 212 reviews
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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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Home in Olivebridge
Country Getaway with Mountain View
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 80 reviews
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Cabin in Boiceville
Catskills Mountain River Dream House
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 281 reviews
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Home in Accord
Private Retreat b/t Mohonk & Woodstock - Sleeps 8
3 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 108 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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Home in Stone Ridge
Spacious Luxe farmhouse, Pool, Sauna, Private
4 bedrooms, 8 beds, 4.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 81 reviews
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Home in Olivebridge
High Point Mountain House ~ Summer on the Mtn!
5 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.94 out of 5 average rating, 119 reviews
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Cottage in Accord
Stunning architect-designed contemporary cabin
2 bedrooms, 2 queen beds, 3 bathrooms
7–12 Sept
4.97 out of 5 average rating, 39 reviews
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Guest house in Woodstock
Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
1 bedroom, 4 beds, 1.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 457 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
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Cottage in Bearsville
Coldbrook Cottage
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 198 reviews
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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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Cottage in Boiceville
The Cottage
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 239 reviews
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Home in Shokan
West Wing - a unique private space w/deck
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 178 reviews
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Home in Kerhonkson
Modern Woodland Getaway with Hot Tub and Fire Pit
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 258 reviews
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Home in Accord
The Woods House, 40 secluded acres & speedy wifi!
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 156 reviews