Hillsdale Vacation Rentals from SAR 262: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Hillsdale has to offer?

Modern Luxurious Cabin, Catskills - The Tiny Nook : This vacation home rental outside of Hillsdale is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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

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Our top choices for Hillsdale vacation rentals

A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

1. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

Richard M.

SAR 1,290 total

includes taxes & fees

15 Nov - 16 Nov

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

2. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

SAR 803 total

includes taxes & fees

14 Nov - 15 Nov

3. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

SAR 778 total

includes taxes & fees

15 Nov - 16 Nov

A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

4. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

SAR 2,198 total

includes taxes & fees

14 Nov - 15 Nov

A large building with a prominent tower, surrounded by trees and a winding road.

5. Berkshire Mountain Lodge

Pittsfield

Susan J

SAR 406 total

includes taxes & fees

6 Dec - 7 Dec

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

6. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

SAR 434 total

includes taxes & fees

19 Nov - 20 Nov

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

7. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Mike

SAR 778 total

includes taxes & fees

14 Dec - 15 Dec

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

8. Micosta Leisure Inn

Hudson

George

SAR 347 total

includes taxes & fees

24 Nov - 25 Nov

A sandy beach with a lake and forest in the background.

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

Kristin O.

SAR 1,220 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Great Barrington

Janet G.

SAR 1,136 total

includes taxes & fees

13 Dec - 14 Dec

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

11. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Eric H.

SAR 1,086 total

includes taxes & fees

14 Nov - 15 Nov

An outdoor seating area with wicker furniture and a view of a forested landscape.

12. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

Hillsdale

SAR 5,704 total

includes taxes & fees

14 Nov - 15 Nov

A dining area with a wooden table, chairs, and a ceiling fan.

13. A Cozy Berkshire Escape l Close to the Slopes

Great Barrington

Kelly B.

SAR 1,126 total

includes taxes & fees

16 Nov - 17 Nov

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

14. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington

SAR 1,380 total

includes taxes & fees

20 Nov - 21 Nov

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

15. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

SAR 1,536 total

includes taxes & fees

18 Nov - 19 Nov

A cabin with a triangular window, wooden walls, and a bed with pillows.

16. Gather Greene

Coxsackie

Jabari

SAR 1,109 total

includes taxes & fees

4 Dec - 5 Dec

A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

17. Hudson NY’S Country Serenity Guest Suite.

Hudson

David P.

SAR 1,353 total

includes taxes & fees

15 Nov - 16 Nov

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

SAR 4,520 total

includes taxes & fees

20 Nov - 21 Nov

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

19. All comforts of home

Hudson

Douglas

SAR 463 total

includes taxes & fees

25 Nov - 26 Nov

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

SAR 2,503 total

includes taxes & fees

16 Nov - 17 Nov

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Top Hillsdale Hotel Reviews

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

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

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

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

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

The Brooks Motel

Hillsdale

10/10 Excellent

The best highway Motel you'll ever visit! In terms of optimization, this "revamped" Motel uses sufficient products to make it feel luxury (i.e. concrete floors, yet coated. A plastic shower, but a premium showerhead with sufficient pressure). An incredibly expensive, comfortable bed, but a $90 TV... The examples go on and on. This place is priced at a 20% premium (around $150 per-might), however the upstate demand is there. I admire the craftsmanship. The place is adorable and unpretentious....

Michael

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

10/10 Excellent

Joseph

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

Quality Inn Great Barrington

Downtown Great Barrington

10/10 Excellent

Andrew

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

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

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

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

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

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

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 breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

Frequently Asked Questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

What are some of the best vacation rentals that Hillsdale has to offer?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Hillsdale is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Hillsdale?

With 46 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.

Hillsdale Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillsdale vacation rentals

1. Ideal location for summer and winter activities with plenty of outdoor space.

2. The Brooks Motel: Exceptional Suite

3. The Brooks Motel: Exceptional Suite

4. Fantastic 2-bedroom house with AC in quaint Hillsdale.

5. Berkshire Mountain Lodge

6. Cozy 1-bedroom studio in serene Great Barrington with AC

7. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

8. Micosta Leisure Inn

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

10. Home in Great Barrington

11. Sweet Cozy Victorian in Housatonic. Close to everything.

12. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

13. A Cozy Berkshire Escape l Close to the Slopes

14. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

15. Cheerful 3-bedroom cottage with woodstove

16. Gather Greene

17. Hudson NY’S Country Serenity Guest Suite.

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

19. All comforts of home

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Find vacation rentals that suit your style

Top Hillsdale Hotel Reviews

Little Cat Lodge

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Hillsdale?

What are some of the best vacation rentals that Hillsdale has to offer?

How many vacation rentals are there in Hillsdale?

What’s there to see and do in Hillsdale?

What’s a vacation rental in Hillsdale like?