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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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Top guest favourite
Home in West Shokan
Mid-Century Retreat ‘POOL IS OPEN and steaming!
2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Olivebridge
High Point Mountain House ~ Summer on the Mtn!
5 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 119 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
1–6 Oct
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
1–6 Oct
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Top guest favourite
Home in Olivebridge
Catskills Hudson Valley Family Hideaway
4 bedrooms, 4 queen beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 86 reviews
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Guest favourite
Room in Stone Ridge
VlyHouse - Room 3
1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 81 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
Cabin in Olivebridge
Ravenscliff-Zen Mt. Retreat STR Permit # 22-10
5 bedrooms, 7 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 75 reviews
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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, 251 reviews
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Top guest favourite
Guest suite in Mount Tremper
Peaceful Catskill Mountain Hideaway
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 320 reviews
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Top guest favourite
Home in Shokan
West Wing - a unique private space w/deck
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.96 out of 5 average rating, 181 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, 217 reviews
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Top guest favourite
Home in Olivebridge
Country Getaway with Mountain View
3 bedrooms, 5 beds, 2.5 bathrooms
27 Oct – 1 Nov
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
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Shokan
Historic Catskills farmhouse with sweeping views
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 122 reviews
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Top guest favourite
Home in Kerhonkson
Fall Farmhouse: Private, Firepit & Fireplace
3 bedrooms, 3 beds, 3 bathrooms
4–9 Oct
4.98 out of 5 average rating, 192 reviews
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Guest favourite
Home in Napanoch
Modern Catskill Home with Spectacular Views
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Cottage in Bearsville
Coldbrook Cottage
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 199 reviews