
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

Hot Tub, Playground, 3 Acres, and Much More!

Charming cottage with Hot Tub -PET FRIENDLY

Renovated Country Cottage w/ Hot Tub & View

Country Cottage w/ HOT TUB & Views

Stream Come True | Hot Tub, Ski, Hike, Relax

Woodstock Carriage House HotTub FirePit Pool

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Pet-friendly cottage rentals

Lake house-lake drained for repairs

Peace Cottage

Woodstock Dog Friendly Cozy Cottage in Town + Yard

Charming creekside cottage in Phoenicia

The Hickory Cottage - perfect!

Catskills Country Cottage

1930's Cottage charm cozy air cond. near hiking

Mountain views, mid-century style! 1 mile to town.
Private cottage rentals

Cozy cottage with local art

Intimate Cottage on Private Estate

The Little House

Little Cottage Under the Ridge

Direct streamside with private stream access

Blue Haven in the Catskills

Woodstock Mountain Cottage

Mod Scandinavian! Tiny Flower Farm
Quick stats about cottage rentals in Olive
Total rentals
20 properties
Nightly prices starting at
R2,093 ZAR before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Rentals with a fireplace Olive
- Pet-friendly rentals Olive
- Rentals with outdoor seating Olive
- Rentals with a patio Olive
- House rentals Olive
- Waterfront rentals Olive
- Rentals with a washer and dryer Olive
- Rentals with pools Olive
- Family-friendly rentals Olive
- Cabin rentals Olive
- Fitness-friendly rentals Olive
- Rentals with a fire pit Olive
- Rentals with a hot tub Olive
- Cottage rentals Ulster County
- Cottage rentals New York
- Cottage rentals United States
- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Bash Bish Falls State Park
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Taconic State Park
- Mount Peter Ski Area
- Villa Roma Ski Resort
- Opus 40
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Plattekill Mountain
- Benmarl Winery
- Bull's Bridge Golf Club