Hillsdale 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 Hillsdale

Cozy Riverside Berkshires Retreat

Great Barrington MA

$282 nightly

$314 total

Jun 22 - Jun 23

Total with taxes and fees

With a stay at this vacation home in Great Barrington, you'll be on a river, within a 15-minute drive of National Shrine of the Divine Mercy and Housatonic River.

Modern Lakefront Retreat

Saugerties NY

With a stay at this vacation home in Saugerties, you'll be within a 10-minute drive of HITS-on-the-Hudson and Esopus Creek.

Kitchen

Washer

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Sharon CT

Located in Sharon, this vacation home is on the waterfront, within a 10-minute drive of North East Town Hall and Veterans Field.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham NY

$339 nightly

$380 total

Jun 20 - Jun 21

Total with taxes and fees

Located in Chatham, this vacation home is a 5-minute drive from The Mac-Haydn Theatre and 8 minutes from Hudson Chatham Winery.

Hamptons on the Hudson in South Saugerties

Glasco NY

With a stay at this vacation home, you'll be centrally located in Glasco, within a 15-minute drive of HITS-on-the-Hudson and South Landing.

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

East Chatham NY

Located in East Chatham, this vacation home is within a 15-minute drive of Queechy Lake and New Lebanon Library.

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Red Hook NY

Located in Red Hook, this vacation home is a 4-minute drive from Red Hook Golf Club and 6 minutes from Museum of Rhinebeck History.

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY

Located in Hillsdale, this vacation home is in the mountains, within a 15-minute drive of Hillsdale Town Hall and Ebenezer II Gifts and Antiques.

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Charming cottage with lake access, wood burning fire place, and WiFi

Elizaville NY

When you stay at this vacation home in Elizaville, you'll be 9 minutes by car from Tousey Winery.

Large Barn styled vacation home that fits groups with space to spare.

Craryville NY

With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito Island.

BRAND NEW 4 story home minutes from Warren St w/ a King Suite!

Hudson NY

With a stay at this vacation home in Hudson, you'll be within a 10-minute drive of Olana State Historic Site and Hudson Area Library.

Don't see what you're looking for?

See all available properties in Hillsdale

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.