Cottage vacation rentals in Olive
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Olive
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Olive cottage rentals
Cottage rentals with a hot tub
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
Cottage in Phoenicia
4.89 out of 5 average rating, 817 reviewsRomantic hot tub cottage.Breweries/swimming nearby
Cottage in Woodstock
4.9 out of 5 average rating, 381 reviewsFamous Architect - Streamside Cottage w/ hot tub
Cottage in Kerhonkson
4.82 out of 5 average rating, 146 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Cottage in Andes
4.97 out of 5 average rating, 102 reviewsSecluded Romantic Cottage
Cottage in Kerhonkson
4.84 out of 5 average rating, 258 reviewsStony Kill Ranch - Hot Tub and Waterfall Access
Cottage in Denver
4.96 out of 5 average rating, 111 reviewsCountry Cottage w/ HOT TUB & Views
Cottage in Pine Bush
5 out of 5 average rating, 100 reviewsCatskills Cottage (w/ Hot Tub) on Top of the World
Pet-friendly cottage rentals
Cottage in Kerhonkson
4.91 out of 5 average rating, 158 reviewsPet-friendly private cabin—spring dates now open!
Cottage in Kerhonkson
4.86 out of 5 average rating, 168 reviewsKerhonkson cottage in the woods with stream
Cottage in Saugerties
4.93 out of 5 average rating, 225 reviewsChic & Cozy Cottage 10 mins to Woodstock
Cottage in Kingston
4.91 out of 5 average rating, 310 reviewsKapitan's Cottage Tranquil Hidden Salt Pool Open
Cottage in Woodstock
5 out of 5 average rating, 127 reviewsLuxury+firepit+stream+walk/town=Brook Cottage Too
Cottage in Kerhonkson
4.89 out of 5 average rating, 457 reviewsMod Scandinavian! HudsonValley!tiny Flower Farm
Cottage in West Shokan
4.8 out of 5 average rating, 153 reviewsBarn style Home
Cottage in Phoenicia
4.93 out of 5 average rating, 221 reviewsCharming creekside cottage in Phoenicia
Private cottage rentals
Cottage in Phoenicia
4.91 out of 5 average rating, 584 reviewsRomantic Getaway: Lovingly Restored Esopus Cottage
Cottage in Ulster Park
4.94 out of 5 average rating, 188 reviewsHidden Gem Cottage — cozy escape to play or WFH
Cottage in Tillson
4.99 out of 5 average rating, 111 reviewsCozy cottage with local art
Cottage in Clintondale
4.93 out of 5 average rating, 169 reviewsThe cottage at Maple Ave - upstate mountain view
Cottage in High Falls
4.93 out of 5 average rating, 203 reviewsLeggett Cottage
Cottage in Roxbury
4.98 out of 5 average rating, 488 reviewsThe Little House
Cottage in Phoenicia
4.94 out of 5 average rating, 229 reviewsCozy Catskill Cottage on the Pantherkill
Cottage in Phoenicia
4.97 out of 5 average rating, 164 reviewsDirect streamside with private stream access
Quick stats about cottage rentals in Olive
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
$120 before taxes and fees
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