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Search results; Over 1,000 homes in Olive

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, 133 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, 211 reviews
Top guest favourite
Guest house in Olive
The Lily Cottage Guesthouse
1 bedroom, 1 bed, 1 bathroom
3–8 Nov
4.99 out of 5 average rating, 180 reviews
Guest favourite
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, 175 reviews
Home in Shokan
15min to Phoenicia + Woodstock; Charming Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 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, 236 reviews
Top guest favourite
Barn in Kerhonkson
Barn Studio, Designer Loft and 18' Projection
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Room in Stone Ridge
VlyHouse Room 6
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Treehouse in Lanesville
Edgewood Catskills - Treehouse Cabin
1 bedroom, 1 bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Kerhonkson
The Red Roof Cabin,
1 bedroom, 1 queen bed, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 104 reviews
Top 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, 93 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, 574 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Garden Queen Suite · GF Breakfast
1 queen bed, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 170 reviews
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, 130 reviews
Top guest favourite
Home in New Paltz
Eclectic one-bedroom house
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 318 reviews
Home in Shokan
Chic Catskills Escape | Chef's Kitchen + Firepit
3 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
Top guest favourite
Room in Hyde Park
Scandinavian Design Dutchess County - 1 of 3 rooms
1 king bed, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 691 reviews
Top guest favourite
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, 106 reviews
Guest favourite
Tiny home in Accord
Deer Hill Farm, fire pit, Sauna, Grateful Woods.
1 queen bed, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 178 reviews