Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Hillsdale vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is ￥24,653
￥31,084 total
includes taxes & fees
Feb 23 - Feb 24
The Brooks Motel: Exceptional Suite
Property grounds

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,653
￥31,084 total
includes taxes & fees
Feb 23 - Feb 24
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Loved our stay! Beautiful place and the hosts were very nice. Thank you!"
United States
Kate C.
The price is ￥33,336
￥62,068 total
includes taxes & fees
Feb 24 - Feb 25
HunnyHAUS: Deluxe TINY*private spa*walk to town
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥31,010
￥51,936 total
includes taxes & fees
Mar 9 - Mar 10
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is ￥31,010
￥51,936 total
includes taxes & fees
Mar 9 - Mar 10
BLUSH: Boutique TINY home*private spa*walk to town
View from property

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (158 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is ￥16,900
￥24,950 total
includes taxes & fees
Feb 24 - Feb 25
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is ￥20,147
￥22,566 total
includes taxes & fees
Feb 23 - Feb 24
Micosta Leisure Inn
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥30,390
￥85,841 total
includes taxes & fees
Feb 23 - Feb 24
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥62,020
￥107,205 total
includes taxes & fees
Feb 23 - Feb 24
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor dining

Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties
Saugerties
9.6 out of 10, Exceptional, (11 reviews)
"The home was amazing! Do recommend."
United States
Cole B.
The price is ￥37,429
￥87,420 total
includes taxes & fees
Feb 23 - Feb 24
Charming 2-bedroom Waterfront home with boat access in Saugerties
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
The price is ￥41,724
￥79,029 total
includes taxes & fees
Feb 23 - Feb 24
Umana's Cabin, cozy, comfy, 5+ acres of land
Property grounds

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (53 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,210
￥20,507 total
includes taxes & fees
Feb 23 - Feb 24
All comforts of home
Outdoor spa tub

Cozy Waterfront Oasis – Hot Tub, Sauna, Firepit, Creek Views, Pet Friendly

Cozy Waterfront Oasis – Hot Tub, Sauna, Firepit, Creek Views, Pet Friendly
Saugerties
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in and out process. Property was very clean and host was communicative with clear instruction on use of amenities! Great location with direct water access. "
United States
Lucy N.
The price is ￥58,734
￥109,890 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Waterfront Oasis – Hot Tub, Sauna, Firepit, Creek Views, Pet Friendly
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
8.0 out of 10, Very Good, (47 reviews)
"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.
The price is ￥19,381
￥25,180 total
includes taxes & fees
Feb 25 - Feb 26
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (22 reviews)
"Really comfortable and cozy"
Canada
Lynne H.
The price is ￥27,211
￥53,920 total
includes taxes & fees
Feb 27 - Feb 28
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is ￥46,360
￥100,797 total
includes taxes & fees
Feb 23 - Feb 24
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Lobby

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (13 reviews)
"Very comfortable home"
United States
Holly
The price is ￥21,552
￥49,734 total
includes taxes & fees
Feb 23 - Feb 24
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is ￥31,010
￥48,376 total
includes taxes & fees
Mar 1 - Mar 2
Dugway Hideaway Walking Distance to Lime Rock Park
Interior

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is ￥16,900
￥33,515 total
includes taxes & fees
Feb 24 - Feb 25
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥36,747
￥78,283 total
includes taxes & fees
Mar 8 - Mar 9
Cheerful 3-bedroom cottage with woodstove
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."
Jennifer 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Hillsdale

Search for holiday rentals in Hillsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsdale using one of the methods below:

  • View our selection of featured holiday rentals in Hillsdale
  • Use the map to find apartments and other holiday homes in the Hillsdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsdale while they last

Look no further and take a look at our great range of rental properties in Hillsdale!

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?

Pool & Secluded Historic Estate on the Hudson | River House by AvantStay: This vacation home rental outside of Hillsdale is located on a river and has an arcade game room, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Hillsdale?

With 50 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.