Hillsdale Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Hillsdale holiday rentals

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 HK$1,244
HK$1,568 total
includes taxes & fees
3 Mar - 4 Mar
The Brooks Motel: Exceptional Suite
TV, offices

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 HK$1,236
HK$1,560 total
includes taxes & fees
3 Mar - 4 Mar
The Brooks Motel: Exceptional Suite
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 HK$1,479
HK$2,515 total
includes taxes & fees
10 Mar - 11 Mar
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 HK$1,479
HK$2,515 total
includes taxes & fees
10 Mar - 11 Mar
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, (160 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is HK$853
HK$1,259 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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 HK$978
HK$1,271 total
includes taxes & fees
4 Mar - 5 Mar
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (54 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$767
HK$1,035 total
includes taxes & fees
3 Mar - 4 Mar
All comforts of home
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, (10 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is HK$853
HK$1,691 total
includes taxes & fees
3 Mar - 4 Mar
Charming loft cottage in tranquil Germantown with WiFi, AC
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, (35 reviews)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
The price is HK$1,162
HK$2,651 total
includes taxes & fees
3 Mar - 4 Mar
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is HK$831
HK$1,106 total
includes taxes & fees
3 Mar - 4 Mar
All the comforts of home
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, (2 reviews)
"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 HK$2,105
HK$3,970 total
includes taxes & fees
3 Mar - 4 Mar
Umana's Cabin, cozy, comfy, 5+ acres of land
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 HK$1,009
HK$2,442 total
includes taxes & fees
3 Mar - 4 Mar
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
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 HK$1,408
HK$2,769 total
includes taxes & fees
3 Mar - 4 Mar
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,408
HK$2,403 total
includes taxes & fees
3 Mar - 4 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Terrace/patio

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, (15 reviews)
"Cozy and beautiful house. "
United States
Seung L.
The price is HK$873
HK$1,503 total
includes taxes & fees
3 Mar - 4 Mar
Country Cottage with beautiful views and easy access to Catskills activities.
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 HK$3,129
HK$5,497 total
includes taxes & fees
4 Mar - 5 Mar
Guesthouse Cabin vacation rentals in Berkshire County
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 HK$1,533
HK$4,331 total
includes taxes & fees
3 Mar - 4 Mar
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (39 reviews)
"Cute house in a great location. Thanks for the stay!"
United States
Nicole S.
The price is HK$1,331
HK$3,190 total
includes taxes & fees
3 Mar - 4 Mar
Brand New House w gated backyard that is located right at the Saugerties Village
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, (12 reviews)
"Host was very welcoming and house was cozy with all the amenities…I would come back again if in this area!"
United States
Sarah M.
The price is HK$1,889
HK$4,385 total
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom Waterfront home with boat access in Saugerties
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"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 HK$1,260
HK$2,107 total
includes taxes & fees
3 Mar - 4 Mar
Home in Great Barrington
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
"Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience. "
Anthony 2-night trip
Posted 15 hours 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 holiday rental in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, or you can select a more secluded option if you're looking for a relaxing stay. Hillsdale is known for its coffee shops and ski areas.

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

Pool & Secluded Historic Estate on the Hudson | River House by AvantStay: This holiday home rental outside of Hillsdale is located on a river, and has an arcade/games room, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Hillsdale?

With 48 Expedia holiday rentals, you're guaranteed 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 holiday rental in Hillsdale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsdale. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.