Hillsdale, NY Condo Rentals from NT$1,841

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Recommended hotels in Hillsdale

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

1. The Brooks Motel

Hillsdale

Nelson

NT$5,378 total

includes taxes & fees

Nov 7 - Nov 8

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

2. Little Cat Lodge

Copake Falls

Stacy

NT$5,593 total

includes taxes & fees

Dec 3 - Dec 4

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

3. Quality Inn Great Barrington

Downtown Great Barrington

Lynne

NT$2,774 total

includes taxes & fees

Dec 3 - Dec 4

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Cynthia

NT$3,054 total

includes taxes & fees

Dec 7 - Dec 8

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

5. the Alander

Copake

Luis

NT$6,087 total

includes taxes & fees

Nov 20 - Nov 21

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

6. Prospect Berkshires

Egremont

Sunny

NT$9,847 total

includes taxes & fees

Nov 30 - Dec 1

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

7. Monument Mountain Motel

Great Barrington

Phillip

NT$2,195 total

includes taxes & fees

Dec 3 - Dec 4

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

8. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Sherry

NT$2,897 total

includes taxes & fees

Nov 18 - Nov 19

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

9. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Md

NT$5,910 total

includes taxes & fees

Nov 11 - Nov 12

A large house with a balcony and a grassy yard.

10. The Little Lion

Great Barrington

Linda

NT$3,046 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

11. East Rock Inn

Great Barrington

Sharon

NT$4,513 total

includes taxes & fees

Dec 7 - Dec 8

A dining table with pastries, a coffee pot, and a vase of sunflowers.

12. Granville House

Housatonic

Cynthia

NT$8,425 total

includes taxes & fees

Nov 7 - Nov 8

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

13. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

NT$3,940 total

includes taxes & fees

Dec 3 - Dec 4

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

14. Changing Times Boutique Country Lodging

Craryville

Thomas

NT$7,354 total

includes taxes & fees

Dec 6 - Dec 7

15. Quality Inn Lee - Lenox South

Lee

James

NT$3,111 total

includes taxes & fees

Dec 2 - Dec 3

A room with a round table and two chairs, a window with a view of trees and a building, and an air conditioning unit.

16. Econo Lodge Lee - Great Barrington

Lee

Fernando

NT$2,057 total

includes taxes & fees

Dec 6 - Dec 7

A group of people performing yoga in an outdoor setting with grass and trees.

17. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

NT$2,251 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale

A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top reviews in Hillsdale

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Quality Inn Great Barrington

Downtown Great Barrington

10/10 Excellent

Andrew

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

The White Hart

Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

Monument Mountain Motel

Great Barrington

10/10 Excellent

We have stayed here a half dozen times, and if you are simply looking for a clean place to lay your head for the night with no frills, then this place is perfect! The rooms have always been clean and everything in good working order. So what that they don't have breakfast...there is an AMAZING breakfast spot right across the street. Take HALF the money you saved by avoiding big name hotels and you'll get a much better breakfast! We've never had noise issues, never felt "unsafe", and the staff is...

Anthony

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

Frequently Asked Questions

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How can I find cheap condos in Hillsdale?

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What is there to do in Hillsdale near my condo?

If you'd like to discover the best of Hillsdale, be sure to stop by Catamount Aerial Adventure Park. It's a favorite with locals and visitors alike.

Search Condo Rentals in Hillsdale

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Hillsdale

1. The Brooks Motel

2. Little Cat Lodge

3. Quality Inn Great Barrington

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

5. the Alander

6. Prospect Berkshires

7. Monument Mountain Motel

8. Travelodge by Wyndham Great Barrington Berkshires

9. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10. The Little Lion

11. East Rock Inn

12. Granville House

13. The Black Swan Lee - Lenox, an Ascend Collection Hotel

14. Changing Times Boutique Country Lodging

15. Quality Inn Lee - Lenox South

16. Econo Lodge Lee - Great Barrington

17. Pleasant Valley Motel West Stockbridge

Learn more about Hillsdale

Top reviews in Hillsdale

Little Cat Lodge

10/10 Excellent

Frequently Asked Questions

Why book your condo in Hillsdale with Expedia?

How can I find cheap condos in Hillsdale?

What is there to do in Hillsdale near my condo?