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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 Olivebridge
Catskills Hudson Valley Family Hideaway
3 bedrooms, 3 queen beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Home in Shokan
Historic Catskills farmhouse with sweeping views
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 122 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, 71 reviews
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, 242 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
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 Boiceville
‘Little Silver’ Your Fun Getaway in the Catskills
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 19 reviews
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, 53 reviews
Guest favourite
Home in Olivebridge
Olive Woods House - Catskills Mountain Views
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 94 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 Olivebridge
High Point Mountain House ~ Summer on the Mtn!
5 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 119 reviews
Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 7 beds, 3.5 bathrooms
11–16 Sept
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, 197 reviews
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, 215 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, 48 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
Home in Mount Tremper
Esopus Creek Farmhouse | Near Woodstock
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
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, 576 reviews