Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Hillsdale

Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$133 nightly
The price is $150
Dec 6 - Dec 7
Total with taxes and fees
Micosta Leisure Inn
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Saugerties
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Dec 7 - Dec 8
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 7 - Dec 8
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Coxsackie
10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
Sioux Tipi on Chloe's Lake
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill
9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
$307 nightly
The price is $332
Dec 7 - Dec 8
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Dec 11 - Dec 12
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

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

Lenox
10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Old Chatham
9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
1 bedroom, desk, free WiFi
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook
9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
$191 nightly
The price is $216
Dec 5 - Dec 6
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Property grounds
Private Yacht on Catskill Creek

Private Yacht on Catskill Creek

Catskill
9.8 out of 10, Exceptional, (28)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
United States
Jay
Private Yacht on Catskill Creek
Interior
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Catskill
9.4 out of 10, Exceptional, (18)
"The house is so historic and very beautiful/interesting. We had a great time. "
United States
Berta T.
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Outdoor dining
Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties

Saugerties
9.4 out of 10, Exceptional, (9)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
$469 nightly
The price is $525
Dec 8 - Dec 9
Total with taxes and fees
Charming 2-bedroom Waterfront home with boat access in Saugerties
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington
10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (150)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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.
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Top Hillsdale Hotel Reviews

voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

10/10 Excellent
"Beautiful room and very clean"
Mariam 1-night trip
Posted 3 days ago
voco James Newbury Hudson Valley by IHG

Find out more about Hillsdale

Everything you need to know about Hillsdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsdale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsdale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsdale. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillsdale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillsdale rentals

At Expedia, we put the best Hillsdale vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillsdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsdale vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

What are some of the best vacation rentals that Hillsdale has to offer?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Hillsdale?

With 53 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.