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Compare 96 Apartments in Hillsdale with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Cozy Modern Studio Apt in Glasco
Interior
Cozy Modern Studio Apt in Glasco
The price is AED 466
AED 702 total
includes taxes & fees
22 Nov - 23 Nov
Cozy Modern Studio Apt in Glasco
Charming Apartment In Berkshire Victorian Home
Exterior
Charming Apartment In Berkshire Victorian Home
7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
Cozy Studio
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
10.0 out of 10, Exceptional, (172)
"We had a wonderful, relaxing time. Beautiful spot. The property was very comfortable. I would stay there again."
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
Dugway Hideaway Walking Distance to Lime Rock Park
Dugway Hideaway Walking Distance to Lime Rock Park
9.0 out of 10, Wonderful, (9)
"Great location and super easy to navigate!"
The price is AED 735
AED 1,157 total
includes taxes & fees
22 Nov - 23 Nov
Dugway Hideaway Walking Distance to Lime Rock Park
The Brooks Motel: Exceptional Suite
The Brooks Motel: Exceptional Suite
10.0 out of 10, Exceptional, (2)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is AED 584
AED 704 total
includes taxes & fees
22 Nov - 23 Nov
The Brooks Motel: Exceptional Suite
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Hip on Warren
Living area
Hip on Warren
10.0 out of 10, Exceptional, (8)
"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 1,462 total
includes taxes & fees
22 Nov - 23 Nov
Hip on Warren
Private apartment in beautiful country barn
Living area
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Exterior
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
9.4 out of 10, Exceptional, (11)
"Cute, quite apartment on the second floor. Enjoyed coffee on the small deck looking out at the farm animals on a cool, crisp and sunny fall morning. Perfect place as base camp for our weekend adventures in the area!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Main Street Delight 1bedroom
Living area
Main Street Delight 1bedroom
10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
Private kitchen
Heart of Lenox!! - renovated downtown apartment
10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
9.6 out of 10, Exceptional, (21)
"Nice little cabin on a beautiful piece of property. The dirt road leading to the house was very narrow and bumpy but looks like they were in the process of smoothing out the road. The cabin is very cute inside and clean. We had three people so inside there’s not a lot of seating but it’s a tiny house so there’s not a lot of space for them to add additional seating. Just something to keep in mind. They do allow dogs. Our dog really enjoyed swimming in the pond. Wish they’d had a hose to bath her...
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Lighthouse Walk - Full Floor Suite in the heart of Downtown
Living area
Lighthouse Walk - Full Floor Suite in the heart of Downtown
8.8 out of 10, Excellent, (12)
"Lovely place to stay! Would stay here again for sure."
Lighthouse Walk - Full Floor Suite in the heart of Downtown
Village Apt
Room
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
Living area
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
Gateway to the Berkshires - Renovated downtown apartment
Room
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
Downtown Hudson Apartment: Walk to Cafes & River!
Hudson Vacation Rental | 2BR | 1BA | 650 Sq Ft | Stairs Required
Downtown Hudson Apartment: Walk to Cafes & River!
10.0 out of 10, Exceptional, (1)
"A great find in Hudson, NY. Location was perfect for exploring downtown. Host was helpful when we needed something. Washer & dryer were nice amenities to have while traveling. Definitely would recommend for anyone staying in the area! "
Downtown Hudson Apartment: Walk to Cafes & River!
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Exterior
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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

Micosta Leisure Inn
Terrace/patio
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is AED 424
AED 458 total
includes taxes & fees
25 Nov - 26 Nov
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 525
AED 812 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Cabin Overlooking Chloe's Lake
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.2 out of 10, Very Good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AED 459
AED 533 total
includes taxes & fees
24 Nov - 25 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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?
There are plenty of places to stay in Hillsdale with 69 hotels and other lodging accommodations. Though there aren’t many apartments, we can help you find accommodations with similar amenities. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. Even filter by similar properties such as vacation homes, condos, or cabins.
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 top apartments in the area: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 16.6 mi/26.7 km away in Lee. Private patios and fireplaces are included. Garfield House Studio at 208: 16.6 mi/26.8 km away in Lee. Amenities include private patios. Hip on Warren: It’s located in Hudson, 14.1 mi/22.7 km from Hillsdale. Includes free WiFi and Smart TVs.
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.