Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Hillsdale vacation rentals

TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,864
￥31,351 total
includes taxes & fees
Jan 2 - Jan 3
The Brooks Motel: Exceptional Suite
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4)
"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 ￥24,864
￥31,351 total
includes taxes & fees
Jan 3 - Jan 4
The Brooks Motel: Exceptional Suite
Fridge, microwave, stovetop, coffee/tea maker
Brooks Motel: Perfect Suite, Seasonal Waterviews

Brooks Motel: Perfect Suite, Seasonal Waterviews

Brooks Motel: Perfect Suite, Seasonal Waterviews
Hillsdale
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
The price is ￥22,519
￥28,724 total
includes taxes & fees
Jan 6 - Jan 7
Brooks Motel: Perfect Suite, Seasonal Waterviews
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
HunnyHAUS: Deluxe TINY*private spa*walk to town
Property grounds
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"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 ￥33,637
￥56,455 total
includes taxes & fees
Jan 13 - Jan 14
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

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (6)
"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 ￥31,276
￥53,432 total
includes taxes & fees
Jan 6 - Jan 7
BLUSH: Boutique TINY home*private spa*walk to town
Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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, (117)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is ￥17,147
￥25,274 total
includes taxes & fees
Jan 6 - Jan 7
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Terrace/patio
Experience Peace in this Cozy country cottage nestled beneath the mountains

Experience Peace in this Cozy country cottage nestled beneath the mountains

Experience Peace in this Cozy country cottage nestled beneath the mountains
Catskill
9.8 out of 10, Exceptional, (9)
"The cottage was comfortable and spotless. My family thoroughly enjoyed their stay at the cottage, and they loved the setting. "
United States
Patricia C.
The price is ￥20,173
￥44,249 total
includes taxes & fees
Jan 2 - Jan 3
Experience Peace in this Cozy country cottage nestled beneath the mountains
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

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, (8)
"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 ￥17,045
￥33,803 total
includes taxes & fees
Jan 4 - Jan 5
Charming loft cottage in tranquil Germantown with WiFi, AC
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is ￥20,320
￥22,760 total
includes taxes & fees
Jan 2 - Jan 3
Micosta Leisure Inn
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
The price is ￥15,482
￥27,849 total
includes taxes & fees
Jan 4 - Jan 5
Country Cottage with beautiful views and easy access to Catskills activities.
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,630
￥57,196 total
includes taxes & fees
Jan 4 - Jan 5
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥19,243
￥37,130 total
includes taxes & fees
Jan 8 - Jan 9
Berkshires Apartment at the Stephentown Hotel
Property grounds
All comforts of home

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,341
￥20,683 total
includes taxes & fees
Jan 3 - Jan 4
All comforts of home
Outdoor dining
Charming Cottage in the Heart of Catskill & Pet Friendly

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, (18)
"Perfect place for a visit to the Hudson Valley. Very comfortable and well taken care of. Friendly neighbors. 3 blocks from Downtown Catskill"
United States
Kirk N.
The price is ￥28,148
￥53,369 total
includes taxes & fees
Jan 4 - Jan 5
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

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, (34)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
The price is ￥23,504
￥51,899 total
includes taxes & fees
Jan 5 - Jan 6
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds
All the comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is ￥16,608
￥22,105 total
includes taxes & fees
Jan 4 - Jan 5
All the comforts of home
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

'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.
The price is ￥19,548
￥25,397 total
includes taxes & fees
Jan 4 - Jan 5
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥23,655
￥40,228 total
includes taxes & fees
Jan 5 - Jan 6
Home in Great Barrington
Fridge, microwave, oven, stovetop
1 Bedroom | Cozy Lounge | Spacious

1 Bedroom | Cozy Lounge | Spacious

1 Bedroom | Cozy Lounge | Spacious
2.0 star property
Catskill
1 Bedroom | Cozy Lounge | Spacious
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We chose this location for our family Christmas getaway because the amenities looked appealing and the price was affordable—and we were more than pleased with our three-night stay. The property is incredibly family-friendly. The pool and arcade had great hours, and while the arcade was small, it offered a fun selection of games. The pool and outdoor hot tub were kept at perfect temperatures, and even when busy, there was plenty of space for everyone. Relaxing in the hot tub during a snowstorm was one of the highlights of our trip. Each night, the common room hosted a movie night, which was wonderful to see families come together and enjoy time as a group. The front desk also offered DVD and game rentals, and it was refreshing to see families playing classic board games and laughing together—a pastime that seems rare these days. The lobby and common areas were spacious and cozy, especially with the warm fireplaces, where our family spent a few hours each evenings playing games. Our suite was roomy, comfortable, and felt like home. The well-stocked kitchen was a bonus. The staff was friendly and accommodating, and having a Stop & Shop directly across the street was incredibly convenient. We are more than pleased with this establishment and would both recommend and return for another family getaway! "
Katelyn 3-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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
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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?

Hamptons on the Hudson in South Saugerties: This vacation home rental outside of Hillsdale is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Hillsdale?

With 51 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.