Highland Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Highland

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Kingston NY

$250 nightly

$279 total

Nov 9 - Nov 10

Total with taxes and fees

With a stay at this vacation home in Kingston, you'll be on a river, just steps from Catskill State Park and a 4-minute drive from Thorn Preserve - Catskill Center.

Kitchen

Pet friendly

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh NY

When you stay at this vacation home in Newburgh, you'll be on the waterfront, within a 5-minute drive of Town of Newburgh Little League and Ice Time Sports Complex.

Kitchen

Washer

The Chicken Coop

Staatsburg NY

Located in Staatsburg, this vacation home is in a rural location, within a 10-minute drive of Margaret Lewis Norrie State Park and Ogden Mills and Ruth Livingston Mills State Park.

Kitchen

Washer

Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Millbrook NY

Located in Millbrook, this vacation home is in the mountains, within a 10-minute drive of Institute of Ecosystem Studies and Innisfree Garden.

Pool

Kitchen

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet NY

Located in Carmel, this vacation home is in the mountains, a 4-minute drive from Clarence Fahnestock State Park and 8 minutes from Chuang Yen Monastery.

Kitchen

Washer

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill NY

$311 nightly

$359 total

Nov 3 - Nov 4

Total with taxes and fees

Located in Fishkill, this vacation home is a 4-minute drive from Blodgett Memorial Library and 5 minutes from Northeast Regional Epilepsy Group.

Kitchen

Washer

New Paltz Modern Zen Cabin

New Paltz NY

With a stay at this vacation home in New Paltz, you'll be within a 5-minute drive of Huguenot Street Historic District and New Paltz Golf Course.

Hot Tub

Kitchen

Owl's Nest: A Pet-Friendly Nature Lover's Getaway near Wineries & Hiking Trails

Marlboro NY

When you stay at this vacation home in Marlboro, you'll be 14 minutes by car from Live At The falcon.

Kitchen

Washer

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

Wallkill NY

$127 nightly

$142 total

Nov 1 - Nov 2

Total with taxes and fees

Free Cancellation

With a stay at this vacation home in Wallkill, you'll be within a 15-minute drive of Tuthilltown Spirits and Jenkinstown Day Spa.

Pet friendly

Free WiFi

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland NY

$627 nightly

$702 total

Nov 1 - Nov 2

Total with taxes and fees

Located in Highland, this vacation home is within a 10-minute drive of Apple Greens Golf Course and Franny Reese State Park.

Kitchen

Pet friendly

Relaxing Retreat with Firepit & A+ Design | Charcoal Chalet by AvantStay

New Paltz NY

When you stay at this vacation home in New Paltz, you'll be in the mountains, within a 5-minute drive of Huguenot Street Historic District and New Paltz Golf Course.

Kitchen

Washer

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Beacon NY

Located in Beacon, this vacation home is within a 5-minute drive of Hudson River and Mount Gulian Historic Site.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Highland

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.