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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, 182 reviews
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
Guest favourite
Home in Shokan
15min to Phoenicia + Woodstock; Charming Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
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, 212 reviews
Top guest favourite
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
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
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, 53 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, 239 reviews
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
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
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 Kingston
BRAND NEW! This New House Three
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in West Shokan
Mid-Century Retreat ‘POOL IS OPEN!’
2 bedrooms, 2 beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Boiceville
Winston's Place - Woodland Cozy Catskills Cabin
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 576 reviews
Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
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, 55 reviews
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, 51 reviews
Top guest favourite
Cottage in Grahamsville
“Green Meadow Cottage”, updated 1850’s farmhouse.
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Accord
Happy Hemlock | Modern Luxury Retreat
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews