Search Vacation Homes in Hillsdale

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 575 Vacation Homes in Hillsdale with updated reviews, rates, and availability.

Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Fridge, microwave, oven, stovetop
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (87)
"Very nice property. Very nice owner. No problems noted."
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is $504
includes taxes & fees
$451 per night
Oct 6 - Oct 7
Cheerful 3-bedroom cottage with woodstove
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Shower, hair dryer, towels
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
10.0 out of 10, Exceptional, (11)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Hudson River Way by Woodstock Way Hotel
Panoramic House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Hudson River Way by Woodstock Way Hotel
5.0 star property
Hudson River Way by Woodstock Way Hotel
Spectacular views and close to Great Barrington.
Smart TV, fireplace
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
9.4 out of 10, Exceptional, (18)
"Stayed here to attend a family wedding in Catskills. Gorgeous views despite rainy weekend. Property as described. Would stay again."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
4-bedrooms with gym+spa access steps from Garlic Festival
Spa
4-bedrooms with gym+spa access steps from Garlic Festival
9.0 out of 10, Wonderful, (12)
"We enjoyed our stay and Chris was very responsive to any questions. Would definitely stay again."
4-bedrooms with gym+spa access steps from Garlic Festival
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
"We had a wonderful stay as a group of 6 adults and 2 children. The house was very comfortable and clean. We appreciated the well stocked kitchen and excellent set up for kids. The location felt private but was still only a few minutes drive from Great Barrington. Thank you for a great visit! "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Historic Saugerties Home w/ Deck: River Views!
Fridge, microwave, stovetop, dishwasher
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (12)
"Very peaceful location in our favorite Hudson Valley town, sweet Saugerties! The property manager was extremely responsive, the neighbors were very nice — one even recommended a local swimming hole — and the house was very cute and unique. We loved waking up to the sound of birds and the sunrise over the Hudson. We also loved being able to walk into the village center for dinner and ice cream. The house was clean, comfortable, and we very much enjoyed our stay. "
Historic Saugerties Home w/ Deck: River Views!
Private Access To Laurel Lake, Enjoy Lake Life
Property grounds
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Garfield Townhouse in the Berkshires on Main St
Fridge, microwave, oven, stovetop
Garfield Townhouse in the Berkshires on Main St
10.0 out of 10, Exceptional, (8)
"We very much enjoyed our stay at Garfield House and hope to be back someday. Our host Jeff was responsive and available for anything we needed. The unit was clean and set up just as shown. Highly recommend to anyone interested in staying in a great Berkshire town."
Garfield Townhouse in the Berkshires on Main St
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Property grounds
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Catskills Getaway w/ Hot Tub on 45 Acres!
Fridge, microwave, stovetop, dishwasher
Catskills Getaway w/ Hot Tub on 45 Acres!
9.0 out of 10, Wonderful, (4)
"This property was a perfect location for seclusion but close enough to anything you may want! Cute and Cozy house, VERY clean and comfortable. Hot tub was AMAZING! Thank you Rich"
Catskills Getaway w/ Hot Tub on 45 Acres!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Rockspring by AvantStay | Huge Berkshires Estate
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.6 out of 10, Excellent, (11)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Fridge, microwave, oven, stovetop
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
Pool
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (6)
"The location could not be better in terms of being close to West Stockbridge yet also feeling very remote and with beautiful views. The pool was great. We thoroughly enjoyed ourselves."
Wellspring by AvantStay | Indoor Pool + Views
Don't see what you're looking for?
See all available properties in Hillsdale
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.
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

Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is $128
includes taxes & fees
$119 per night
Sep 25 - Sep 26
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, (40)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is $145
includes taxes & fees
$145 per night
Sep 22 - Sep 23
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Interior
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.