Search Hillsdale Villa Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Browse Select Hillsdale Villas

The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
The Kemble- Built by a US Secretary of State in Lenox
Catskill Villa/Pool with Hudson River View
Interior

Catskill Villa/Pool with Hudson River View

9.0 out of 10, Wonderful, (2)
"Really enjoyed our stay and the town."
Catskill Villa/Pool with Hudson River View
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Property grounds

5k+ Sq Ft of Luxury Living on 54 Acres near Hudson

8.0 out of 10, Very good, (5)
"Property was perfect for our group trip. The house was clean, spread out, well air-conditioned during the summer, and provided a number of sleeping options (easily sleeping 10). The outside was perfect for our guys-trip - lots of space, nice patio with overhang, and the pool was incredible. Overall the house was great, and Gautam was a great host - easy to communicate with, providing additional air mattresses and towels in every room. The house is 15-20 minutes from Hudson/Catskill towns, and...
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Terrace/patio

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Secluded Art & Architecture in Nature Retreat - hi
Interior

Secluded Art & Architecture in Nature Retreat - hi

Secluded Art & Architecture in Nature Retreat - hi
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.
Don't see what you're looking for?
See all available properties in Hillsdale
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Hillsdale

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

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

10.0 out of 10, Exceptional, (11)
"We had our family Thanksgiving at this home and it was a great time. Enough space to cook a Thanksgiving meal, have a baking contest, play board games, and relax. The bedrooms were comfortable and everyone commented on how well they slept. More than enough bathrooms and showers with hot water for six people. Close to Great Barrington and Stockbridge for some small town vibes. Overall a great stay!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.6 out of 10, Excellent, (9)
"We always live these cabins & we've been coming for years!"
The price is CA $173
CA $240 total
includes taxes & fees
Apr 30 - May 1
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Lovely, and quiet, with water nearby. Everything was nice and worked, and owner responded to communication quickly. Will visit again! "
The price is CA $180
CA $194 total
includes taxes & fees
May 19 - May 20
Micosta Leisure Inn
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.

Frequently asked questions

Why book your villa in Hillsdale with Expedia?
Use Expedia to find your dream villa in Hillsdale. Traveling with the family? Make use of our filters to search for stays with amenities like a pool. If you’re on a budget, select how much you’d like to spend and the star rating of the property. We’ll help you find the perfect fit that suits your style and taste.
How can I find cheap villas in Hillsdale?
With Expedia’s helpful filter tool, booking cheap villas in Hillsdale is easy. To discover accommodations that give you the most bang for your buck, narrow your search results by amenities, budget and star rating.
What is there to do near my villa in Hillsdale?
The perfect travel accessory is a well-thought-out travel plan. Catamount Aerial Adventure Park is a wonderful spot to start your adventures in Hillsdale.