Cottage vacation rentals in Olive
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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, 805 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
Cottage in Kerhonkson
4.85 out of 5 average rating, 142 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Cottage in Andes
4.97 out of 5 average rating, 101 reviewsSecluded Romantic Cottage
Cottage in Kerhonkson
4.84 out of 5 average rating, 254 reviewsStony Kill Ranch - Hot Tub and Waterfall Access
Cottage in Mongaup Valley
4.98 out of 5 average rating, 160 reviewsHot Tub, Playground, 3 Acres, and Much More!
Cottage in Denver
4.96 out of 5 average rating, 110 reviewsCountry Cottage w/ HOT TUB & Views
Pet-friendly cottage rentals
Cottage in Kerhonkson
4.86 out of 5 average rating, 162 reviewsKerhonkson cottage in the woods with stream
Cottage in Bloomington
4.98 out of 5 average rating, 470 reviews'The Blue Jay Cottage' - Privacy With A View!
Cottage in West Shokan
4.8 out of 5 average rating, 153 reviewsBarn style Home
Cottage in Woodstock
4.85 out of 5 average rating, 121 reviewsRock City Writer's Studio: bucolic•sauna•walkable!
Cottage in Phoenicia
4.93 out of 5 average rating, 217 reviewsCharming creekside cottage in Phoenicia
Cottage in Tannersville
4.9 out of 5 average rating, 208 reviewsSpruce House on Gooseberry Creek
Cottage in Kerhonkson
4.89 out of 5 average rating, 449 reviewsMod Scandinavian! HudsonValley!tiny Flower Farm
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Private cottage rentals
Cottage in Highland
4.91 out of 5 average rating, 542 reviewsLittle Yellow Cottage New Paltz - Kitchen wash/dry
Cottage in Phoenicia
4.94 out of 5 average rating, 225 reviewsCozy Catskill Cottage on the Pantherkill
Cottage in Lanesville
4.94 out of 5 average rating, 165 reviewsCreekfront Cottage between Phoenicia & Hunter Mtn.
Cottage in Woodstock
4.99 out of 5 average rating, 278 reviewsGrapevine Cottage
Cottage in Tillson
4.99 out of 5 average rating, 108 reviewsCozy cottage with local art
Cottage in Roxbury
4.98 out of 5 average rating, 482 reviewsThe Little House
Cottage in Ulster Park
4.94 out of 5 average rating, 186 reviewsHidden Gem Cottage — cozy escape to play or WFH
Cottage in Saugerties
4.98 out of 5 average rating, 181 reviewsBlue Mountain Cottage
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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