Hillsdale Holiday Rentals, New York: Private House Rentals

A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Go beyond your typical stay in Hillsdale

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Our top choices for Hillsdale hotels

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

A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

A dining area with a wooden table, chairs, and a colorful striped rug.

A snow-covered landscape with a house and a sign that reads "the brooks".

1. The Brooks Motel

Hillsdale

Nelson

3.801.443 ₫

4.257.614 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A house with a stone patio and wooden stools.

2. Little Cat Lodge

Copake Falls

Kees

4.669.674 ₫

5.230.035 ₫ total

includes taxes & fees

16 Sept - 17 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

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

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

Great Barrington

BJORN

2.894.103 ₫

3.232.713 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Great Barrington

Lisa

4.188.627 ₫

4.678.696 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A motel with a parking lot and several cars parked.

5. Monument Mountain Motel

Great Barrington

Charlie

2.229.242 ₫

2.489.972 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

6. Quality Inn Great Barrington

Great Barrington

Sisile

2.415.663 ₫

2.698.294 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

7. the Alander

Copake

Phil

3.767.548 ₫

4.219.654 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

8. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

2.216.205 ₫

2.475.501 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a view of the outdoors.

A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

A wooden deck with a staircase leading to a covered porch.

9. Micosta Leisure Inn

Hudson

Andrea

3.027.974 ₫

3.391.706 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden wall with a white pendant light fixture.

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

10. Prospect Berkshires

Egremont

Kellee

8.564.980 ₫

10.440.789 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

11. The Yankee Inn

Lenox

Karen

2.327.104 ₫

2.599.375 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

12. The Little Lion

Great Barrington

Anne

2.933.212 ₫

3.276.398 ₫ total

includes taxes & fees

3 Sept - 4 Sept

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

James

3.324.308 ₫

3.713.252 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A motel with a row of rooms, a parking lot, and a red car parked in front.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

A hotel room with a bed, two chairs, a small table, and a lamp.

14. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

1.971.194 ₫

2.162.400 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A covered porch with white railings and rocking chairs.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

15. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

2.737.665 ₫

3.148.315 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

16. Quality Inn Lee - Lenox South

Lee

Christine

2.858.904 ₫

3.193.396 ₫ total

includes taxes & fees

23 Sept - 24 Sept

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern hotel room with a bed, sofa, leather chair, and a small table.

A tented area with lush greenery and a dining setup.

17. Interlaken Inn & Resort

Lakeville

Stacie

4.985.158 ₫

5.732.931 ₫ total

includes taxes & fees

22 Sept - 23 Sept

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A garden with wooden Adirondack chairs and a stone pathway.

A spacious lobby with a fireplace, seating area, and a bar.

18. Berkshire Mountain Lodge

Pittsfield

Robert

2.075.393 ₫

2.900.685 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

19. East Rock Inn

Great Barrington

ERIK

3.605.622 ₫

4.027.481 ₫ total

includes taxes & fees

22 Sept - 23 Sept

A wooden deck with white railings and hanging flower baskets.

A building with a balcony covered in pink flowers, a paved driveway, and a car parked in the background.

A two-story building with a balcony, a red door, and a staircase leading to the second floor.

A bathroom with a bathtub, toilet, and sink. There is a shower curtain, a towel rack, and a hairdryer.

20. Chatham Travel Lodge

Old Chatham

2.916.265 ₫

3.265.904 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)

Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.

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Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.

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Hillsdale Town Hall

This historic former library now serves as Hillsdale's administrative centre with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.

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Mosquito Island

Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.

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Community Library

The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.

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Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.

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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 Hillsdale Hotel Reviews

Berkshires Untold

10/10 Excellent

"The entry , bar, and dining room along with the outside patio was beautifully done. It made you happy to be there as it was so welcoming. Ample parking space, great amenities, and comfy quiet room made our stay great. The only thing missing was a floor lamp in our room so we couldn’t read at night as the small lamps were dim."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Breakfast was the weakest thing, but it was free, loved the hot tub and having a couch in our room"

Quality Inn Great Barrington

8/10 Good

"It is a good value for money. Location is very good, right on the main street, just one block away from downtown Great Barrington with almost all the restaurants and shops within walking distance. Downside is that it is a motel, not a standard hotel. If you have a room on the second floor then you have to haul your luggage up as there is no elevator. Breakfast has bare minimum items. It would help if fresh fruit and cereal is added. There is improvement possible in the overall upkeep. However, I'll certainly recommend it for a short stay for budget customers like me."

Pocketbook Hotel and Bath

10/10 Excellent

"It's rare to find a place that entices you to stay put because the room is so comfortable, the food is delicious, the staff is warm and inviting, and because the amenities (the baths!) are plentiful. We had a fantastic stay and will be back again!"

Howard Johnson by Wyndham Saugerties

8/10 Good

"Clean comfortable room and restaurant."

Hotel On North

8/10 Good

"Nice room! Comfortable bed. Super friendly staff."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It was clean and amenities were above average."

St. Charles Hotel

8/10 Good

"Place was clean. Bed was comfortable. Air conditioning was very loud!!"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.619.133 ₫

1.808.571 ₫ total

3 Sept - 4 Sept

includes taxes & fees

5.4/10 (890 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.059.767 ₫

2.300.760 ₫ total

3 Sept - 4 Sept

includes taxes & fees

7.6/10 Good! (907 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.327.104 ₫

2.599.375 ₫ total

14 Sept - 15 Sept

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.415.663 ₫

2.698.294 ₫ total

22 Sept - 23 Sept

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

3.076.614 ₫

3.436.682 ₫ total

8 Sept - 9 Sept

includes taxes & fees

9.2/10 Wonderful! (182 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

4.734.205 ₫

6.528.151 ₫ total

22 Sept - 23 Sept

includes taxes & fees

8.6/10 Excellent! (71 reviews)

Hotels in Hillsdale with star rating

Frequently asked questions

What's the seasonal weather 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.

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Book Hotels in Hillsdale on Expedia.com

Find hotels in Hillsdale, NY from 1.808.571 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillsdale

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Hillsdale hotels

1. The Brooks Motel

2. Little Cat Lodge

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

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

5. Monument Mountain Motel

6. Quality Inn Great Barrington

7. the Alander

8. Travelodge by Wyndham Great Barrington Berkshires

9. Micosta Leisure Inn

10. Prospect Berkshires

11. The Yankee Inn

12. The Little Lion

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

14. Pleasant Valley Motel West Stockbridge

15. Locust Tree Bed and Breakfast LLC

16. Quality Inn Lee - Lenox South

17. Interlaken Inn & Resort

18. Berkshire Mountain Lodge

19. East Rock Inn

20. Chatham Travel Lodge

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Mosquito Island

Community Library

Roe Jan Brewing Co.

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Berkshires Untold

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Quality Inn Great Barrington

Pocketbook Hotel and Bath

Howard Johnson by Wyndham Saugerties

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Best Western Plus Berkshire Hills Inn & Suites

St. Charles Hotel

More cheap stays in Hillsdale

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

The Yankee Inn

Quality Inn Great Barrington

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pocketbook Hotel and Bath

Hotels in Hillsdale with star rating

Frequently asked questions

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