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Compare 95 Apartments in Hillsdale with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (13)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
"Lovely quiet spot with plenty of eating options around the area. Well maintained."
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Saugerties Modern Private Waterfront 2BR Village Walk to All Kayaks Pet Friendly

2.5 star property
10.0 out of 10, Exceptional, (6)
"We had an excellent overnight stay here. Beautiful water view and walking-distance to shops in town. In a blizzard, the temperature control kept us warm and the driveway was plowed by the morning. Great communication, smooth logistics."
The price is SAR 1,185
SAR 2,238 total
includes taxes & fees
16 Feb - 17 Feb
Saugerties Modern Private Waterfront 2BR Village Walk to All Kayaks Pet Friendly

All comforts of home

9.8 out of 10, Exceptional, (37)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is SAR 409
SAR 517 total
includes taxes & fees
9 Feb - 10 Feb
All comforts of home

Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

9.4 out of 10, Exceptional, (12)
"We had a great trip to this lovely home! Clean and cute, near beautiful nature and easy access to grocery stores."
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (30)
"Great place with amazing views and super close to a ski resort highly recommend "
Modern Copake Falls Getaway

Hip on Warren

10.0 out of 10, Exceptional, (9)
"Apartment is adorable and right on Warren that has everything you could want for a quick visit to upstate NY. Restaurants , stores of all kinds and great coffee shops and bars. "
The price is SAR 1,031
SAR 1,500 total
includes taxes & fees
8 Feb - 9 Feb
Hip on Warren

Modern Private Waterfront 3BR Saugerties Village Walk to All Kayaks Pet Friendly

2.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect place very clean very detailed You have everything you need , The owner always make sure that everything is good with us with definitely recommend"
The price is SAR 1,441
SAR 2,452 total
includes taxes & fees
12 Feb - 13 Feb
Modern Private Waterfront 3BR Saugerties Village Walk to All Kayaks Pet Friendly

Village Apt

9.8 out of 10, Exceptional, (6)
"Beautiful bathroom and kitchen. Lovely clean linens, etc. only issue was the very steep stairs to bathroom and living spaces. Several stairs are breaking and the rail is disconnecting from the wall in the middle. Also, adorable kitchen table top not secured to bottom. Shifts a bit if you are not aware. Lovely stay though!"
Village Apt

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lovely bright apartment in pastoral shaker barn

10.0 out of 10, Exceptional, (2)
"We traveled from Arizona for a class reunion and stayed in apartment. The property was clean and well appointed. We were able to host a dinner with four family members we had not seen in years! Another highlight was sitting outside by the fire pit in the evening. The property host, Michelle, provided excellent check in instructions and answered any questions very promptly. This property worked out very well for us, but if you have an issue with stairs you might want to check out the other...
Lovely bright apartment in pastoral shaker barn

Downtown Hudson Apartment: Walk to Cafes & River!

10.0 out of 10, Exceptional, (2)
"Great little place! Well equipped with everything we needed. Would stay at again…easy for visiting family nearby."
Downtown Hudson Apartment: Walk to Cafes & River!

Lighthouse Walk - Full Floor Suite in the heart of Downtown

8.8 out of 10, Excellent, (13)
"Plenty of good eats in walking distance. Very clean! Host is an effective communicator who responds right away. Very happy with our stay!!"
Lighthouse Walk - Full Floor Suite in the heart of Downtown

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (24)
"Lovely apartment in a great location "
51 Church Street, Lenox MA - One Bedroom Unit

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
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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Other property types in Hillsdale

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 897
SAR 1,002 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations

Postcard Cabins Eastern Catskills

2.0 star property
7.4 out of 10, Good, (3)
"This tiny cabin was a dream. It has everything you need for a cozy, nature getaway. "
The price is SAR 469
SAR 506 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Eastern Catskills

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
11 Feb - 12 Feb
Berkshire Village Carriage House - Super Private!!
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.

Frequently asked questions

What's it like to stay at an apartment in Hillsdale?
You can search through 5 apartments in Hillsdale for your stay.
How do you know if an apartment is a good option for you?
An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay in a quieter area.
What's a favorite apartment I should consider for a stay in Hillsdale?
Here are some of the favorite apartments in the area: The Brooks Motel: Exceptional Suite: Located 1 mi/1.6 km away in Hillsdale. Amenities include sofa beds. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: It’s situated in Great Barrington, 8.6 mi/13.8 km away. Includes free WiFi, separate dining areas, and Smart TVs. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: 16.6 mi/26.7 km away in Lee. Private patios and fireplaces are included.
How many apartments are there in Hillsdale?
Expedia has 5 apartments to book in Hillsdale.
What can I expect from the weather in Hillsdale?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Hillsdale. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit in Hillsdale?
Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. Catamount Aerial Adventure Park and Catamount Ski Area are other places to visit while you’re in town.
What's the best way to get to and around Hillsdale?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) from the city center. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.