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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 AED 1,166
AED 2,027 total
includes taxes & fees
4 Mar - 5 Mar
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 AED 400
AED 506 total
includes taxes & fees
4 Mar - 5 Mar
All comforts of home

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

9.4 out of 10, Exceptional, (13)
"Cute little apartment in a cute and quiet street. Loved our stay!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (31)
"Cozy modern apartment with great views. Very close to Catamount and a short drive to Great Barrington. Michael was a great host."
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 AED 1,010
AED 1,469 total
includes taxes & fees
4 Mar - 5 Mar
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 AED 1,388
AED 2,373 total
includes taxes & fees
4 Mar - 5 Mar
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, (2)
"Beautiful, freshly renovated place. Host was super responsive and generous (helped us enormously when we had to reschedule). Very comfortable beds! Location was great, quiet and surrounded by trees yet just 5 minutes from the skiing area. Highly recommended!"
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, (25)
"This property hit the 5 star marks all over. Access was amazing to our weekend. Host was so precise with check in instruction and overall information. This property was very very clean, comfortable and the light that entered all of the rooms made the stay warm and inviting. 5 Star for us. "
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

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is AED 643
AED 694 total
includes taxes & fees
11 Mar - 12 Mar
Postcard Cabins Eastern Catskills

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties
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: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 8.6 mi/13.8 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. All comforts of home: Located in Hudson, 13 mi/20.9 km away. Includes private balconies. Access to a hot tub is available on site. 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. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: It’s situated in Richmond, 18.5 mi/29.8 km from Hillsdale.
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.