Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Hillsdale vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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.
$179 nightly
The price is $200
Jan 20 - Jan 21
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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.
$179 nightly
The price is $200
Jan 19 - Jan 20
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9 reviews)
"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.
$355 nightly
The price is $400
Jan 26 - Jan 27
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Dining

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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.
$320 nightly
The price is $361
Jan 26 - Jan 27
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (6 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.
$320 nightly
The price is $361
Jan 20 - Jan 21
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
View from property

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (131 reviews)
"I loved every single part of the stay "
United States
Srijana
$150 nightly
The price is $162
Jan 26 - Jan 27
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (135 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
$120 nightly
The price is $135
Jan 19 - Jan 20
Total with taxes and fees
Micosta Leisure Inn
Property grounds

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Jan 19 - Jan 20
Total with taxes and fees
All comforts of home
Interior

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
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.
$192 nightly
The price is $215
Jan 21 - Jan 22
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Outdoor dining

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
$294 nightly
The price is $326
Jan 20 - Jan 21
Total with taxes and fees
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Interior

Aparthotel in Spencertown

Suite 4 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (3 reviews)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
$243 nightly
The price is $272
Jan 25 - Jan 26
Total with taxes and fees
Suite 4 - Quiet and private accommodations in a country setting.
Outdoor dining

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (21 reviews)
"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.
$225 nightly
The price is $243
Jan 21 - Jan 22
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Beach

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3 reviews)
"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.
$212 nightly
The price is $226
Jan 19 - Jan 20
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, stovetop, dishwasher

Vacation Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
$510 nightly
The price is $563
Jan 19 - Jan 20
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Terrace/patio

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (13 reviews)
"Great spot!"
United States
Dylan
$172 nightly
The price is $192
Jan 19 - Jan 20
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
Smart TV

Apartment in Red Hook

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
9.2 out of 10, Wonderful, (14 reviews)
"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.
$193 nightly
The price is $218
Jan 19 - Jan 20
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Lobby

Cottage in Catskill

Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
9.8 out of 10, Exceptional, (10 reviews)
"The cottage was comfortable and spotless. My family thoroughly enjoyed their stay at the cottage, and they loved the setting. "
United States
Patricia C.
$289 nightly
The price is $312
Jan 19 - Jan 20
Total with taxes and fees
Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
Property grounds

Vacation Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29 reviews)
"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.
$138 nightly
The price is $155
Feb 2 - Feb 3
Total with taxes and fees
All the comforts of home
Exterior

Cabin in Saugerties

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.
$145 nightly
The price is $162
Jan 21 - Jan 22
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Interior

Vacation Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
$342 nightly
The price is $383
Jan 22 - Jan 23
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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

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 $132 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental outside of Hillsdale offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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. You can relax into your vacation with a selection of games and a hot tub.

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.