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Featured Apartments in Hillsdale and around

Lighthouse Walk - Full Floor Suite in the heart of Downtown

9.0 out of 10, Wonderful, (17)
"Easy to check in and out. Right off main Street so minutes from great coffee, great books, and a handful of bars in town. "
Lighthouse Walk - Full Floor Suite in the heart of Downtown

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

9.6 out of 10, Exceptional, (5)
The price is €214
includes taxes & fees
2 Sept - 3 Sept
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

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

9.4 out of 10, Exceptional, (66)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

All comforts of home

9.8 out of 10, Exceptional, (47)
"Very clean, well-appointed, quiet location. Relaxing and pleasant."
The price is €117
includes taxes & fees
1 Sept - 2 Sept
All comforts of home

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.4 out of 10, Exceptional, (3)
"Seemingly brand-new, lovely setting, perfect location, gracious hosts. Easy drive to Tanglewood if that's what brings you to the area. The pictures were 100% correct - no staging done here. For folks-music fans, the topper is that you're across the alley from the historical location of "Alice's Restaurant" from Arlo Guthrie's famous song of the same name. "
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

Renovated Apartment on Main St.

6.0 out of 10, (2)
"Beautiful natural light, clean and overlooking Main Street in Salisbury. Extremely well equipped with pillows, blankets, towels, clean, new bedding. I imagine an artist writing a song or a novel here. Walkable to shops, a market, grazing sheep and the best cold brew and pastries you can find anywhere. "
Renovated Apartment on Main St.

Dugway Hideaway Walking Distance to Lime Rock Park

9.4 out of 10, Exceptional, (13)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
Dugway Hideaway Walking Distance to Lime Rock Park

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment

Glasco Waterfront Oasis/10 min from HITS

10.0 out of 10, Exceptional, (1)
"Host was a pleasure"
The price is €211
includes taxes & fees
8 Sept - 9 Sept
Glasco Waterfront Oasis/10 min from HITS

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (28)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (85)
"Easy access to restaurants and shopping . Clean and nicely decorated. Apartment has everything we needed for a relaxing Stay."
Apartment In Historic 1785 Thomas Jenkins House

Apartment with spa access Steps from Diamond Mills Resort/Village

10.0 out of 10, Exceptional, (6)
"Quiet and relaxing"
Apartment with spa access Steps from Diamond Mills Resort/Village

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."
The price is €179
includes taxes & fees
1 Sept - 2 Sept
The Brooks Motel: Exceptional Suite

Walk to Dtwn Hudson: Cozy Upstate Apartment

5.0 out of 10, (2)
"The apt was in an older home but it had a separate entrance. It's a quaint and quirky place and it suited our needs and budget perfectly.We enjoyed the walkability factor as it is very close to Warren Street.During our stay, there was a plumbing issue with the downstairs tenant, But the hostess was very gracious about it and made arrangements with a plumber immediately.A very pleasant stay overall. Thank you."
Walk to Dtwn Hudson: Cozy Upstate Apartment

Charming Waterfront 3BR, Hot Tub, Kayaks, Sauna, Pet Friendly,

2.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful property with great amenities! Wphld definitely stay there again!"
The price is €706
includes taxes & fees
3 Sept - 4 Sept
Charming Waterfront 3BR, Hot Tub, Kayaks, Sauna, Pet Friendly,

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (10)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice apartment. Beautiful grounds and gardens. We enjoyed ourselves. It was a very comfy place to return to as we enjoyed Jacob's Pillow and our other explorations around the Berkshires. "
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (33)
"Great place with amazing views and super close to a ski resort highly recommend "
Modern Copake Falls Getaway
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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Frequently asked questions

What's it like to stay at an apartment in Hillsdale?
You can search through 5 apartments in Hillsdale for your holiday.
How do you know if an apartment is a good option for you?
Often more spacious than a traditional hotel room, an apartment includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for solo travellers who want to stay in a quieter area.
What's a favourite apartment for my stay in Hillsdale?
Below are some of the favourite apartments in the area: The Brooks Motel: Exceptional Suite: Located 1 mi/1.6 km away in Hillsdale . Amenities include a sofa bed . Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.: It's located in Saugerties , 23.7 mi/38.2 km away. Lighthouse Walk - Full Floor Suite in the heart of Downtown: 23 mi/37 km away in Saugerties . Free WiFi, a patio and a Smart TV are included . THE ARTIST'S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi: It's located in Red Hook , 21.4 mi/34.5 km from Hillsdale. Includes free WiFi and a Smart TV .
How many apartments will I find in Hillsdale?
Expedia has 5 apartments to book in Hillsdale.
What can I expect from the weather during my trip to Hillsdale?
Although 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 temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm 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 you save you a headache when you get to your destination. Fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) from the heart of the city. 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, you may want a rental car for your journey.