
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

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

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Lovely Cottage w/ Jacuzzi+Woodstove!

Country Cottage w/ HOT TUB & Views

Hot Tub & Chic Catskills Woodstock Design Retreat

Stream come true! Ski, spa, hike, flow, relax...

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

Woodstock Carriage House HotTub FirePit Pool
Pet-friendly cottage rentals

Peace Cottage

Herb Cottage: history•art•woodstove•walk to town!

Bellwood Cottage 8-14min to all Roxbury Wed Venues

Seclusion and Romance - Hot Tub is hot hot hot

*spring-ready* Pet-friendly private cabin!

Catskills Country Cottage

Modern Forest Retreat on a Tranquil HilltopSAUNA

Magnolia Cottage
Private cottage rentals

Lakeside Cabin

‘Clavashack’ Country Cottage

Creekside Cottage

The Rest Cottage/Heated Pool/Soaking Tub/Fire Pit

Kapitan’s Cottage:Private Retreat Upstate Pets ok!

Hidden Gem Cottage — cozy escape to play or WFH

Direct streamside with private stream access

Creekfront Cottage between Phoenicia & Hunter Mtn.
Quick stats about cottage rentals in Olive
Total rentals
10 properties
Nightly prices starting at
G$23,080 GYD before taxes and fees
Total number of reviews
1.4K 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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- Waterfront rentals Olive
- Rentals with pools Olive
- Rentals with a fire pit Olive
- Rentals with a fireplace Olive
- Rentals with a patio Olive
- Rentals with outdoor seating Olive
- Family-friendly rentals Olive
- Pet-friendly rentals Olive
- Fitness-friendly rentals Olive
- House rentals Olive
- Kid-friendly rentals Olive
- Rentals with a washer and dryer Olive
- Cabin rentals Olive
- Rentals with a hot tub Olive
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Thunder Ridge Ski Area
- Walkway Over the Hudson State Historic Park
- Mohawk Mountain Ski Area
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Opus 40
- Hudson Highlands State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Villa Roma Ski Resort
- Thaddeus Hait Farm
- Plattekill Mountain
- Bull's Bridge Golf Club
- Mount Peter Ski Area