Hinsdale, MA Vacation Homes from AED 719

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Our top choices for Hinsdale vacation homes

A wooden deck with a table and chairs, surrounded by a white railing.

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

AED 1,654 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

AED 719 total

includes taxes & fees

3 Nov - 4 Nov

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

AED 1,312 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a sofa, armchairs, a coffee table, and a television.

4. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

AED 2,206 total

includes taxes & fees

3 Nov - 4 Nov

5. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

AED 1,886 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

6. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

AED 1,042 total

includes taxes & fees

5 Nov - 6 Nov

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

7. Ellie’s Overlook, best view in the Berkshires!

Richmond

"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...

Delaney M.

AED 2,393 total

includes taxes & fees

7 Nov - 8 Nov

A spacious living room with a dining area, a kitchen, and a large window.

8. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

AED 778 total

includes taxes & fees

5 Nov - 6 Nov

A hot tub with a string of lights above it, set against a dark night sky.

9. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

AED 1,375 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with a sofa, armchair, coffee table, and TV.

10. Spacious Central Berkshires Home for Groups

Lee

neil s.

AED 2,086 total

includes taxes & fees

3 Nov - 4 Nov

A room with a large window, two sofas, and a small table.

11. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Richmond

AED 4,595 total

includes taxes & fees

13 Nov - 14 Nov

A white two-story house with a porch, surrounded by trees and a hill.

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

AED 1,508 total

includes taxes & fees

3 Nov - 4 Nov

A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

13. Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

AED 4,670 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

14. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

AED 3,771 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

15. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

AED 2,257 total

includes taxes & fees

3 Nov - 4 Nov

An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

16. Maya's Garden House

Great Barrington

AED 4,622 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

17. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robert B.

AED 2,087 total

includes taxes & fees

3 Nov - 4 Nov

18. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Great Barrington

AED 4,887 total

includes taxes & fees

14 Nov - 15 Nov

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

19. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

AED 2,027 total

includes taxes & fees

22 Nov - 23 Nov

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

20. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

AED 3,028 total

includes taxes & fees

23 Nov - 24 Nov

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Top Hinsdale Hotel Reviews

Berkshires Untold

10/10 Excellent

"We had a great stay. The lobby is beautiful- very warm and inviting. Don’t let the motel style fool you. The staff was very welcoming! Room was very spacious. We enjoyed sitting at the fire pit on a chilly fall night. Only suggestion would be softer pillows."

Quality Inn Great Barrington

10/10 Excellent

"This motel was exactly what we were looking for during our short stay. It was clean comfortable and easy to access. The bathroom toilet flushing mechanism was a bit slow/occasionally needed two flushes. There are train tracks behind the building and there is a train that will come by at night that is relatively loud. The breakfast had warm options and was satisfactory. Limited fresh fruit options but overall met our needs. I would stay here again and maybe request the front of the building to limit train noise."

Room 1

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Check prices for these dates

Our top choices for Hinsdale vacation homes

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2. NEW RENO - Chalet-style farm loft near Tanglewood

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

4. Sun Filled Lenox Retreat - Minutes to Tanglewood!

5. Comfortable Berkshires retreat on mtn resort, SISO

6. Real Estate: Therapy - Lake, Laundry, Love it

7. Ellie’s Overlook, best view in the Berkshires!

8. 1800s Carriage house in Berkshires / Hudson Valley

9. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

10. Spacious Central Berkshires Home for Groups

11. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley