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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
9.8 out of 10, Exceptional, (6)
"The place was what we imagined- the rooms were great size and the decor was homey with links of beautiful pottery. It was nice to have seasoning and tea in house. It took a while to figure out the water temp in shower. Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming Apartment In Berkshire Victorian Home
8.0 out of 10, Very Good, (6)
"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
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
9.0 out of 10, Wonderful, (8)
"Very clean. Easy to check in. Bed was a bit too hard for our liking. But overall great!"
The price is AED 735
AED 1,157 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Dugway Hideaway Walking Distance to Lime Rock Park
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 715 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
The Brooks Motel: Exceptional Suite
Garfield House Studio at 208
9.6 out of 10, Exceptional, (27)
"Melanie got me settled and the little studio space was perfect for my needs this weekend, I enjoyed the front porch, and the place was spotless. The Murphy bed was very comfortable. Thanks for making me feel at home!"
Garfield House Studio at 208
Hip on Warren
10.0 out of 10, Exceptional, (7)
"This was the absolute best location we ever could have hoped for. We had an easy walk to every place that we wanted to go and on top of that, the apartment is spotless and obviously very well taken care of. Very nice and comfortable space. The host is great to deal with. We would definitely stay here again."
The price is AED 1,010
AED 1,469 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Hip on Warren
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (17)
"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!
9.2 out of 10, Wonderful, (10)
"This apartment was perfect for my partner and I. The space itself was comfortable and well-designed with some details, like potted plants, that you don’t find in many rentals. The drive into Hudson was pretty and we were happy with the decision to stay a little out of town. Highly recommend. "
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Main Street Delight 1bedroom
10.0 out of 10, Exceptional, (18)
"This place was a real treat. The owner was very communicative and made the process as simple as could be. Bed and pillows were very comfortable and the kitchen had what we needed to make a few meals (grocery was just down the road). We have no hesitations about rebooking here on our next Lenox visit."
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
10.0 out of 10, Exceptional, (63)
"This apartment makes a great base from which to enjoy Lenox and the surrounding Berkshires. There's a nice wine bar (Brava) on one side, a gastropub (Firefly) on the other, and several other nice restaurants close by, including excellent pizza at Boema. It's a very short driver to places like The Mount (Edith Wharton's estate), Tanglewood, and lots of great outdoor activities. The apartment itself is very comfortable and well appointed, really nice for two people or a foursome. Wonderful king...
Heart of Lenox!! - renovated downtown apartment
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
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
10.0 out of 10, Exceptional, (5)
"Just the right size. Nice kitchen. Super close to the HITS show grounds. Lots of restaurants and shops within a block or two. Quiet street and safe neighborhood. Clean. Comfortable. Would definitely stay here again."
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
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!
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
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
9.4 out of 10, Exceptional, (56)
"We ran all over the Berkshires. Nice central location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Apartment in Gorgeous Stonybrook Farm
9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm
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
3.0 star property
9.0 out of 10, Wonderful, (88)
"Great! Had everything you could need and a great view of you wanna sit outside! Very friendly and handsome kitty walking around!!! Thank you!"
The price is AED 415
AED 448 total
includes taxes & fees
14 Nov 2024 - 15 Nov 2024
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (218)
"The room was beautiful. A lot of thought was put into what you would need during your stay. The location was convenient to a lot of sights, biking and restaurants. I would definitely stay again. "
The price is AED 525
AED 808 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Berkshire Village Carriage House - Super Private!!
'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
3 Nov 2024 - 4 Nov 2024
'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 67 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 favorite apartments in the area: Hip on Warren: Located 14.1 mi/22.7 km away in Hudson. Free WiFi and Smart TVs are included. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: It’s located in Richmond, 18.5 mi/29.8 km away. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 16.6 mi/26.7 km from Hillsdale. Includes private patios and fireplaces.
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.