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Featured Condos in Hillsdale

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The Ponds at Foxhollow by Capital Vacations

The Ponds at Foxhollow by Capital Vacations

3.0 out of 5.0 3 Foxhollow Drive Route 7, Lenox, MA
2/5
(1 Reviews)
Situated in the entertainment district, this condo is within 3 miles (5 km) of The Mount, Animagic Museum of Animation and Lee Library. Greenock Country Club and Shakespeare and Company are also within 3 miles (5 km).
 
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Elegant 4 BR Condo in Lenox, MA- Completely New- 3 min From Tanglewood

Elegant 4 BR Condo in Lenox, MA- Completely New- 3 min From Tanglewood

770 Summer St, Lenox, MA
Situated in Lenox, this condo is 1.1 mi (1.8 km) from The Mount and within 3 miles (5 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and Shakespeare and Company are also within 3 miles (5 km).
 
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Beautiful, Secluded, Private Resort in the Heart of the Berkshires in Lenox, MA

Beautiful, Secluded, Private Resort in the Heart of the Berkshires in Lenox, MA

3 Fox Hollow Dr, Vanderbilt 23 - upper, two story unit, Lenox, MA
Situated in Lenox, this historic condo is within 3 miles (5 km) of The Mount, Animagic Museum of Animation and Lee Library. Greenock Country Club and Shakespeare and Company are also within 3 miles (5 km).
 
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A Gem Nestled In The Bershires

A Gem Nestled In The Bershires

281 Main St, 3rd Floor, Great Barrington, MA
Situated in Great Barrington, this historic condo is within 1 mile (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite is 2.2 mi (3.6 km) away.
 
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Vacation Condos in Hillsdale

Wandering around in search of the best restaurants, snapping pictures of iconic landmarks, and hiking through local landscapes are just a few of the things you love about taking a vacation. But you sometimes miss the comforts of home during your getaways. Next time, bring home with you! Book a condominium through Travelocity, and you can have all your travel needs met. You’ll still be able to experience Hillsdale, but you won’t have to give up the things you love—like a full kitchen to cook your favorite breakfast, a nice quiet spot to catch up on reading, and easy access to the top sites in the city.

There are tons of vacation condo rentals to suit your travel style. Do you want to stay in downtown condos that will put you in the heart of Hillsdale? Or do you prefer a luxury condo in an upscale neighborhood, conveniently located near the best attractions?

Place yourself in any part of the city and spend your days exploring the new world around you. When you tire of seeing the sights and testing coffee in the local cafes, return to your safe haven—your condo rental. You’ll appreciate that you can sleep in late without worrying about hotel staff knocking on your door, and you can head out onto the city street without being pegged as a tourist.

You don’t have to pay prices that resemble a mortgage when you book a condo through Travelocity. Our variety of vacation rentals will let you—and your wallet—feel like you’ve made the right decision. Browse properties today and start deciding what outfits you’ll pack for the trip.

Top Trending Hotels in Hillsdale

See all 553 properties in Hillsdale
C$185
Silvanus Lodge

Silvanus Lodge

2.0 out of 5.0 9350 State Rte 22, Hillsdale, NY
5/5
(2 Reviews)
Situated in Hillsdale, this motel is 2.3 mi (3.7 km) from Catamount Aerial Adventure Park and 2.9 mi (4.7 km) from Catamount Ski Area. Taconic Trail State Park and W.E.B. Du Bois Boyhood Homesite are also within 9 miles (15 km).
 
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Holiday House Motel

Holiday House Motel

2.0 out of 5.0 2871 State Route 23, Hillsdale, NY
4/5
(1 Reviews)
Situated in the shopping district, this motel is 1.3 mi (2.1 km) from Catamount Aerial Adventure Park and 2 mi (3.2 km) from Catamount Ski Area. Taconic Trail State Park and Mahaiwe Performing Arts Center are also within 12 mi (20 km).
 
C$199
Ideal Location for Summer and Winter Activities With Plenty of Outdoor Space

Ideal Location for Summer and Winter Activities With Plenty of Outdoor Space

24 Tory Hill Rd, Hillsdale, NY
Situated in Hillsdale, this cabin is within 6 miles (10 km) of Catamount Aerial Adventure Park, Catamount Ski Area and Taconic Trail State Park. Claverack Library is 12 mi (19.3 km) away.
 
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.