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

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

1. The Brooks Motel

Hillsdale

Nelson

฿4,904

฿5,492 total

includes taxes & fees

14 Oct - 15 Oct

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

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

A house with a stone patio and wooden stools.

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.

2. Little Cat Lodge

Copake Falls

Stacy

฿5,115

฿5,729 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

A wooden wall with a white pendant light fixture.

3. Prospect Berkshires

Egremont

Conor

฿9,535

฿11,777 total

includes taxes & fees

10 Nov - 11 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.

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

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

Kelly

฿4,831

฿5,397 total

includes taxes & fees

2 Nov - 3 Nov

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 Quality Inn sign, a brick building, and a parking lot with cars.

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

5. Quality Inn Great Barrington

Downtown Great Barrington

Joan

฿2,602

฿2,907 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

6. the Alander

Copake

Joseph

฿5,700

฿6,384 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

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

Great Barrington

Maria Dulce

฿2,783

฿3,109 total

includes taxes & fees

12 Nov - 13 Nov

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

8. Monument Mountain Motel

Great Barrington

Andrea

฿2,007

฿2,241 total

includes taxes & fees

12 Nov - 13 Nov

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

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

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.

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

฿2,649

฿2,959 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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

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

10. Granville House

Housatonic

Cynthia

฿8,517

฿9,513 total

includes taxes & fees

18 Oct - 19 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.

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

11. East Rock Inn

Great Barrington

ERIK

฿4,809

฿5,371 total

includes taxes & fees

13 Nov - 14 Nov

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

12. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

฿4,225

฿4,719 total

includes taxes & fees

1 Nov - 2 Nov

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A living room with a sofa, armchair, coffee table, and a patterned rug.

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

South Lee

Jared

฿3,923

฿5,038 total

includes taxes & fees

11 Nov - 12 Nov

A large house with a balcony and a grassy yard.

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.

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.

14. The Little Lion

Great Barrington

Lidia

฿3,470

฿3,876 total

includes taxes & fees

19 Oct - 20 Oct

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.

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

15. Quality Inn Lee - Lenox South

Lee

Christine

฿3,116

฿3,481 total

includes taxes & fees

2 Nov - 3 Nov

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

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

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

16. The Red Lion Inn

Stockbridge

Stephan

฿5,298

฿7,588 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

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

Saugerties

Linda

฿4,271

฿4,784 total

includes taxes & fees

11 Nov - 12 Nov

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.

18. The Yankee Inn

Lenox

Basil

฿3,565

฿3,982 total

includes taxes & fees

1 Nov - 2 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.

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

Lee

Gustavo

฿3,859

฿4,311 total

includes taxes & fees

8 Nov - 9 Nov

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

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

A two-story house with a porch, a front door, and a mailbox.

A room with a white door, a window, and a wall with various framed pictures.

20. Changing Times Boutique Country Lodging

Craryville

Thomas

฿6,726

฿7,534 total

includes taxes & fees

14 Oct - 15 Oct

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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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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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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

Hotel On North

10/10 Excellent

"Beautiful property, spacious room. Easy parking"

St. Charles Hotel

8/10 Good

"150 year-old hotel with updated/modern rooms & bathrooms. Clean, quiet, comfortable, good rates. Plenty of free parking. Very pleasant stay overall. If there was a business center or gym, I didn't see them, but that also wasn't important to me, and I can't gig the hotel based on something I didn't need anyway. I mention it here in the event that's a must-have for others. Free breakfast consisted of instant oatmeal with a hot water dispenser, tea bags, packaged banana muffins, bread with a toaster, cold cereal with milk. During a three-day stay, I saw scrambled eggs, sausage, and fresh hot coffee once, although there are single servings coffeemakers in guest rooms. No other meal service offered, and there also didn't seem to be other breakfast options available in town."

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

10/10 Excellent

"Very clean and new hotel."

Berkshire Mountain Lodge

8/10 Good

"We really enjoyed our stay at Berkshire Mountain Lodge. For what we paid - we absolutely feel like we got a great bang for our buck. The hotel is clean and well-maintained, and our suite was massive. It included a kitchen with all the bells and whistles (stove/stovetop, microwave, refrigerator, dishwasher), a full size living room, separate bedroom (with a kingsize mattress), and spacious bathroom. It was so comfortable. We absolutely recommend staying here, especially if you're looking for a reasonably priced accommodation."

Quality Inn Lee - Lenox South

10/10 Excellent

"The rooms were clean and parking what’s convenient."

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,082

฿2,326 total

19 Oct - 20 Oct

includes taxes & fees

5.4/10 (923 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿2,602

฿2,907 total

10 Nov - 11 Nov

includes taxes & fees

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

1055 South Street Pittsfield MA

฿3,330

฿3,719 total

10 Nov - 11 Nov

includes taxes & fees

9.2/10 Wonderful! (236 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,565

฿3,982 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,006 reviews)

St. Charles Hotel

16 Park Place Hudson NY

฿6,035

฿6,820 total

26 Oct - 27 Oct

includes taxes & fees

6.6/10 (997 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

฿8,142

฿10,721 total

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (91 reviews)

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. Pocketbook Hotel and Bath and The Yankee Inn 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 59 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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Book Hotels in Hillsdale on Expedia.com

Find hotels in Hillsdale, NY from ฿2,241

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

5. Quality Inn Great Barrington

6. the Alander

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

8. Monument Mountain Motel

9. Travelodge by Wyndham Great Barrington Berkshires

10. Granville House

11. East Rock Inn

12. Courtyard by Marriott Lenox Berkshires

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

14. The Little Lion

15. Quality Inn Lee - Lenox South

16. The Red Lion Inn

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

18. The Yankee Inn

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

20. Changing Times Boutique Country Lodging

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Community Library

Roe Jan Brewing Co.

Mosquito Island

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Hotel On North

St. Charles Hotel

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

Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Berkshires Untold

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

Frequently asked questions

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