Hillsdale Holiday Rentals

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Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Hillsdale

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.0 out of 10, Wonderful, (30)
"Great place "
The price is HK$1,327
HK$1,729 total
includes taxes & fees
13 Jul - 14 Jul
Postcard Cabins Eastern Catskills
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"We had an excellent stay, and would certainly book this place again!"
The price is HK$1,020
HK$1,102 total
includes taxes & fees
16 Jul - 17 Jul
Micosta Leisure Inn
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

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

8.2 out of 10, Very good, (42)
"Perfect place to reconnect with natural world and yourself"
The price is HK$981
HK$1,275 total
includes taxes & fees
23 Jul - 24 Jul
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Sioux Tipi on Chloe's Lake
Exterior

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is HK$863
HK$1,143 total
includes taxes & fees
13 Jul - 14 Jul
Sioux Tipi on Chloe's Lake
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior

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

9.8 out of 10, Exceptional, (26)
"Great location "
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Private kitchen

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is HK$1,109
HK$1,822 total
includes taxes & fees
13 Jul - 14 Jul
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
<br>Escape to our incredibly private home on 30 acres!
Fridge, microwave, oven, stovetop

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (136)
"A wonderful, private house incredibly well stocked clean and comfortable! Perfect location between Saugerties and Woodstock. "
<br>Escape to our incredibly private home on 30 acres!
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

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

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
Private Yacht on Catskill Creek
Property grounds

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (21)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is HK$1,166
HK$1,929 total
includes taxes & fees
13 Jul - 14 Jul
Private Yacht on Catskill Creek
Cozy Modern Studio Apt in Glasco
Interior

Cozy Modern Studio Apt in Glasco

2.0 out of 10, (2)
"I reserved this property and then received a cryptic message stating it was not available for the days I booked. However, the owner never gave a refund and has not responded to messages from me or VRBO. Beware of phony listings!"
The price is HK$897
HK$1,550 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Modern Studio Apt in Glasco
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Terrace/patio

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

10.0 out of 10, Exceptional, (163)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The Tiny Nook is as cute and charming as the listing suggests, and came well equipped for a short getaway. It was easy to find, quiet, and felt secluded, even as the leaves were falling. The hosts were also very responsive and had some great recommendations of nearby places to visit. "
The price is HK$1,766
HK$3,298 total
includes taxes & fees
13 Jul - 14 Jul
Modern Luxurious Cabin, Catskills - The Tiny Nook
Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
Deluxe Queen Room with 2 Queen Beds
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
1 bedroom, desk, WiFi

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

10.0 out of 10, Exceptional, (1)
"We were in town for a wedding and needed a spot close to the farm. This spot was a gem. Tucked away, quiet and clean - my husband, dog and I had a great stay. We were only able to stay for a night but I wish we could have stayed a bit longer. This is a really cute community with nice things to see and do. The host is amazing! We’re so grateful to her. "
The price is HK$1,138
HK$1,918 total
includes taxes & fees
14 Jul - 15 Jul
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Interior

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

9.8 out of 10, Exceptional, (15)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (13)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Charming cottage with lake access, wood burning fire place, and WiFi
Smart TV, fireplace

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (3)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
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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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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Hillsdale is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Hillsdale?

With 52 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.