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

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

1. The Brooks Motel

Hillsdale

Nelson

3.771.263 ₫

4.223.813 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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 house with a stone patio and wooden stools.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

2. Little Cat Lodge

Copake Falls

Stacy

3.934.219 ₫

4.406.323 ₫ total

includes taxes & fees

18 Nov - 19 Nov

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 deck with a dog silhouette against a backdrop of autumn foliage.

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

3. Prospect Berkshires

Egremont

Conor

7.333.011 ₫

9.057.756 ₫ total

includes taxes & fees

18 Nov - 19 Nov

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

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.

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

4. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

1.957.519 ₫

2.186.549 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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

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

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

Great Barrington

3.715.651 ₫

4.150.382 ₫ total

includes taxes & fees

5 Nov - 6 Nov

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 kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

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

Great Barrington

Cynthia

2.327.940 ₫

2.600.309 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

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

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

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

7. the Alander

Copake

Luis

3.622.640 ₫

4.057.357 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

A row of white plastic chairs on a covered outdoor area with a white building in the background.

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.

8. Monument Mountain Motel

Great Barrington

Andrea

1.548.080 ₫

1.729.142 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

9. East Rock Inn

Great Barrington

Sharon

3.391.808 ₫

3.788.650 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A large house with a balcony and a grassy yard.

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.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

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

10. The Little Lion

Great Barrington

David

2.677.131 ₫

2.990.355 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

11. The Red Lion Inn

Stockbridge

Mallory

4.074.413 ₫

5.836.141 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

12. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Ramakrishnan

2.043.414 ₫

2.282.493 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

13. Granville House

Housatonic

Cynthia

6.572.504 ₫

7.341.539 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

14. Wilder House Berkshires

Sheffield

Liliana

4.240.119 ₫

4.736.213 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

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.

15. The Yankee Inn

Lenox

Basil

2.742.856 ₫

3.063.771 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A historic hotel with a prominent tower and a brick facade.

A dining area with a brick fireplace, wooden beams, and a chandelier.

16. Diamond Mills Resort

Saugerties

luping

6.874.665 ₫

8.346.182 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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

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

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

17. Quality Inn Lee - Lenox South

Lee

Lucinda

2.396.485 ₫

2.676.873 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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 dining area with large windows, wooden furniture, and a view of a lake.

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

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

Lee

Gustavo

2.903.287 ₫

3.242.972 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a fireplace, and comfortable seating.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

19. Berkshires Untold

Lenox

Madhavi R

3.367.473 ₫

3.761.468 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

A modern lobby with a reception desk, seating area, and a dining section.

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

20. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Eleanor

3.181.518 ₫

3.563.301 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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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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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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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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Mosquito Island

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

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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

The Yankee Inn

8/10 Good

"Efficient & comfortable. Very good value."

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Red Ranch Motel

8/10 Good

"They need longer curtains to keep the bright lights outside from entering the room, otherwise it was a great stay. Very nice, clean and friendly place."

St. Charles Hotel

8/10 Good

"I stayed at this hotel for an event. There were people in my party who did not have a great experience, but I was given a nice sized room and easy check in and did not have a single problem. The staff was really nice though not always at the desk."

Howard Johnson by Wyndham Saugerties

8/10 Good

"Traveling with my husband for NY Sheep and Wool Festival. Worked for what we needed. Could use updating."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"10/10 experience! Can’t wait to go back! One overnight stay isn’t enough stay for multiple days!!!!"

Quality Inn Great Barrington

10/10 Excellent

"-"

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.839.073 ₫

2.054.244 ₫ total

28 Oct - 29 Oct

includes taxes & fees

5.4/10 (925 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.957.519 ₫

2.186.549 ₫ total

11 Nov - 12 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

2.560.734 ₫

2.860.340 ₫ total

22 Nov - 23 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.742.856 ₫

3.063.771 ₫ total

1 Nov - 2 Nov

includes taxes & fees

St. Charles Hotel

16 Park Place Hudson NY

3.297.915 ₫

3.726.773 ₫ total

20 Nov - 21 Nov

includes taxes & fees

6.6/10 (1,000 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

6.054.984 ₫

8.011.726 ₫ total

15 Nov - 16 Nov

includes taxes & fees

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 1.729.142 ₫

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. Prospect Berkshires

4. Quality Inn Great Barrington

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

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

7. the Alander

8. Monument Mountain Motel

9. East Rock Inn

10. The Little Lion

11. The Red Lion Inn

12. Travelodge by Wyndham Great Barrington Berkshires

13. Granville House

14. Wilder House Berkshires

15. The Yankee Inn

16. Diamond Mills Resort

17. Quality Inn Lee - Lenox South

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

19. Berkshires Untold

20. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Roe Jan Brewing Co.

Community Library

Mosquito Island

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

The Yankee Inn

Hotel On North

Red Ranch Motel

St. Charles Hotel

Howard Johnson by Wyndham Saugerties

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Quality Inn Great Barrington

FairBridge Inn Express

More cheap stays in Hillsdale

FairBridge Inn Express

Quality Inn Great Barrington

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

The Yankee Inn

St. Charles Hotel

Pocketbook Hotel and Bath

Hotels in Hillsdale with star rating

Frequently asked questions

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