Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Hillsdale vacation rentals

Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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 ￥24,901
￥31,573 total
includes taxes & fees
Jan 9 - Jan 10
The Brooks Motel: Exceptional Suite
Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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 ￥24,901
￥31,397 total
includes taxes & fees
Jan 11 - Jan 12
The Brooks Motel: Exceptional Suite
Fridge, microwave, stovetop, coffee/tea maker
Brooks Motel: Perfect Suite, Seasonal Waterviews

Apartment in Hillsdale

Brooks Motel: Perfect Suite, Seasonal Waterviews
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 ￥22,552
￥28,766 total
includes taxes & fees
Jan 9 - Jan 10
Brooks Motel: Perfect Suite, Seasonal Waterviews
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
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 ￥33,671
￥56,513 total
includes taxes & fees
Jan 13 - Jan 14
BLUSH: Boutique TINY home*private spa*walk to town
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
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
Dining
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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 ￥33,671
￥56,513 total
includes taxes & fees
Jan 13 - Jan 14
Sugar Shack - 300 square feet of pure sweetness.
Exterior
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
Micosta Leisure Inn
View from property
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (119)
"Everything was amazing and the staff was great! Really enjoyed my stay will be returning thank you "
United States
Amanda
The price is ￥20,203
￥28,583 total
includes taxes & fees
Jan 11 - Jan 12
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,363
￥20,713 total
includes taxes & fees
Jan 9 - Jan 10
All comforts of home
Lobby
Peaceful warm cozy country cottage nestled beneath the mountains, woodstove

Cottage in Catskill

Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
9.8 out of 10, Exceptional, (10)
"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 ￥20,203
￥43,469 total
includes taxes & fees
Jan 9 - Jan 10
Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook

Vacation Home in Catskill

Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (8)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is ￥25,058
￥53,448 total
includes taxes & fees
Jan 12 - Jan 13
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior
Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
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 ￥17,070
￥33,151 total
includes taxes & fees
Feb 1 - Feb 2
Charming loft cottage in tranquil Germantown with WiFi, AC
Interior
Suite 4 - Quiet and private accommodations in a country setting.

Aparthotel in Spencertown

Suite 4 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (3)
"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
The price is ￥33,358
￥42,798 total
includes taxes & fees
Jan 25 - Jan 26
Suite 4 - Quiet and private accommodations in a country setting.
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
The price is ￥15,504
￥27,889 total
includes taxes & fees
Jan 9 - Jan 10
Country Cottage with beautiful views and easy access to Catskills activities.
Outdoor dining
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,666
￥57,280 total
includes taxes & fees
Jan 9 - Jan 10
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Beach
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
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 ￥20,947
￥38,962 total
includes taxes & fees
Jan 11 - Jan 12
Berkshires Apartment at the Stephentown Hotel
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is ￥21,142
￥58,234 total
includes taxes & fees
Jan 12 - Jan 13
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in 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 ￥24,243
￥41,074 total
includes taxes & fees
Jan 11 - Jan 12
Home in Great Barrington
Property grounds
All the comforts of home

Vacation Home in Hudson

All the comforts of home
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 ￥16,632
￥22,137 total
includes taxes & fees
Jan 9 - Jan 10
All the comforts of home
Exterior
Near Tanglewood: Historic Summer Retreat

Vacation Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (24)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ￥20,438
￥57,270 total
includes taxes & fees
Jan 15 - Jan 16
Near Tanglewood: Historic Summer Retreat
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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental outside 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.