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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Our top choices for Hillsdale hotels

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

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

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.

1. The Brooks Motel

Hillsdale

Nelson

Rp2.610.257

Rp2.923.487 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

2. Little Cat Lodge

Copake Falls

Kees

Rp3.206.427

Rp3.591.198 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

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

Great Barrington

Maria Dulce

Rp2.130.457

Rp2.379.720 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

Bruce

Rp3.028.292

Rp3.382.603 total

includes taxes & fees

1 Oct - 2 Oct

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 wooden desk, a television, a mirror, and a bathroom visible through an open door.

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

5. Quality Inn Great Barrington

Great Barrington

Joan

Rp1.810.888

Rp2.022.761 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

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

6. the Alander

Copake

Thomas

Rp2.586.983

Rp2.897.420 total

includes taxes & fees

30 Sept - 1 Oct

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

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

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Kevin

Rp1.342.725

Rp1.499.824 total

includes taxes & fees

28 Sept - 29 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 cabin with a bed, a chair, and a table by a large window overlooking a lake.

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

8. Prospect Berkshires

Egremont

Kellee

Rp5.881.135

Rp7.169.156 total

includes taxes & fees

28 Sept - 29 Sept

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

A motel with a parking lot and several cars parked.

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

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

9. Monument Mountain Motel

Great Barrington

Victor

Rp1.224.565

Rp1.367.789 total

includes taxes & fees

25 Oct - 26 Oct

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

A lakeside dock with kayaks and a covered boat ramp.

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.

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

Lee

Ann M

Rp2.466.138

Rp2.754.676 total

includes taxes & fees

29 Sept - 30 Sept

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

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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

William

Rp1.933.524

Rp2.159.818 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

12. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

Rp1.102.825

Rp1.209.706 total

includes taxes & fees

28 Sept - 29 Sept

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

13. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

Rp1.414.337

Rp1.579.815 total

includes taxes & fees

28 Sept - 29 Sept

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

A two-story building with a flat roof, solar panels, and a small patio area.

A covered porch with white railings and rocking chairs.

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

14. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

Rp1.879.815

Rp2.161.787 total

includes taxes & fees

28 Sept - 29 Sept

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

15. Quality Inn Lee - Lenox South

Lee

Wendy

Rp1.963.064

Rp2.192.741 total

includes taxes & fees

19 Oct - 20 Oct

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

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

16. Berkshire Mountain Lodge

Pittsfield

Jay

Rp1.425.067

Rp1.991.753 total

includes taxes & fees

1 Oct - 2 Oct

An outdoor patio with a fire pit, seating, and umbrellas.

A long dining table set with multiple wine glasses, water glasses, and folded white napkins.

A bedroom with a large bed, a dresser, a chair, and a table. There are three windows with blinds, and a lamp is on a nightstand.

A bedroom with a bed, a sofa, a wooden bench, a window, and a door.

17. The Millerton Inn

Millerton

Bernadette

Rp4.495.443

Rp5.085.469 total

includes taxes & fees

28 Sept - 29 Sept

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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A covered porch with wicker furniture and hanging flower baskets.

18. The Red Lion Inn

Stockbridge

Stephan

Rp2.820.080

Rp4.039.451 total

includes taxes & fees

30 Sept - 1 Oct

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A room with a fireplace, two striped armchairs, and a floral drape.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

19. Blackberry River Inn

Norfolk

Brian

Rp2.685.450

Rp3.088.267 total

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with white railings and hanging flower baskets.

A hotel room with two queen beds, a desk, a chair, a lamp, and a window with curtains.

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

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

Andrew

Rp2.002.451

Rp2.242.530 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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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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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

The Red Lion Inn

10/10 Excellent

"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."

Quality Inn Great Barrington

10/10 Excellent

"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."

Berkshires Untold

10/10 Excellent

"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

Quality Inn Lee - Lenox South

10/10 Excellent

"Very clean and comfortable. Some of the mechanicals are older but the rooms are quite fresh. Excellent location. Pretty good breakfast. Excellent value."

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Excellent place"

Pocketbook Hotel and Bath

10/10 Excellent

"Lovely. Staff was very helpful and friendly. The rooms were well appointed. We arrived at night and it was a little difficult finding the main entrance but obviously we succeeded"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

Rp1.111.776

Rp1.241.853 total

28 Sept - 29 Sept

includes taxes & fees

5.4/10 (911 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.810.888

Rp2.022.761 total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (1,002 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

Rp1.933.524

Rp2.159.818 total

27 Oct - 28 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

Rp2.040.942

Rp2.279.768 total

20 Oct - 21 Oct

includes taxes & fees

St. Charles Hotel

16 Park Place Hudson NY

Rp2.685.450

Rp3.034.559 total

1 Oct - 2 Oct

includes taxes & fees

6.6/10 (981 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Rp3.853.621

Rp5.163.808 total

26 Oct - 27 Oct

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Quality Inn Great Barrington and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.

If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?

Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options with pools in Hillsdale?

Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn and Pocketbook Hotel and Bath are a couple of other choices that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 56 hotels and other accommodation options to choose from. Find out more about Hillsdale.

What should I see while I'm in Hillsdale?

The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

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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Find hotels in Hillsdale, NY from Rp1.209.706

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. Quality Inn Great Barrington

6. the Alander

7. Travelodge by Wyndham Great Barrington Berkshires

8. Prospect Berkshires

9. Monument Mountain Motel

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

11. The Yankee Inn

12. Pleasant Valley Motel West Stockbridge

13. Howard Johnson by Wyndham Lenox

14. Locust Tree Bed and Breakfast LLC

15. Quality Inn Lee - Lenox South

16. Berkshire Mountain Lodge

17. The Millerton Inn

18. The Red Lion Inn

19. Blackberry River Inn

20. Chatham Travel Lodge

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Community Library

Mosquito Island

Roe Jan Brewing Co.

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

The Red Lion Inn

Quality Inn Great Barrington

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Whitlock

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Pocketbook Hotel and Bath

More cheap stays in Hillsdale

FairBridge Inn Express

Quality Inn Great Barrington

The Yankee Inn

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

St. Charles Hotel

Pocketbook Hotel and Bath

Frequently asked questions

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