Hinsdale Holiday Homes from £161: Search Holiday Homes in Hinsdale

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Our top choices for Hinsdale holiday 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.

includes taxes & fees

13 Oct - 14 Oct

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.

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

Sherwood Forest

Sharon K.

includes taxes & fees

14 Oct - 15 Oct

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

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

includes taxes & fees

14 Oct - 15 Oct

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

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

New Lebanon

Joanna P.

includes taxes & fees

14 Oct - 15 Oct

5. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

includes taxes & fees

13 Oct - 14 Oct

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

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

Sherwood Forest

Frank M.

includes taxes & fees

13 Oct - 14 Oct

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Richmond

includes taxes & fees

17 Oct - 18 Oct

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.

includes taxes & fees

2 Nov - 3 Nov

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

9. Spacious Central Berkshires Home for Groups

Lee

Beth S.

includes taxes & fees

13 Oct - 14 Oct

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

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

Sherwood Forest

William C B.

includes taxes & fees

3 Nov - 4 Nov

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

11. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

includes taxes & fees

18 Oct - 19 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

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

13. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robert B.

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

20 Oct - 21 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

16. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

9 Nov - 10 Nov

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

17. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

includes taxes & fees

13 Oct - 14 Oct

A staircase with a wooden handrail and a white wall with a light switch.

18. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

20. Greylock Cabin

Florida

Margaret M.

includes taxes & fees

8 Nov - 9 Nov

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Top Hinsdale Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"This is my go-to accommodation to visit Williams College in Williamstown."

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!"

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Find out more about Hinsdale

Hinsdale Holiday Homes information

Number of reviews	210
Accommodation	344 Holiday Homes
Lowest Price	£161
Highest Price	£866

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hinsdale holiday homes

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

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

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

5. Comfortable Berkshires retreat on mtn resort, SISO

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

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

8. 1800s Carriage house in Berkshires / Hudson Valley

9. Spacious Central Berkshires Home for Groups

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

11. Stylish Mid-century Modern Berkshires Cape

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

13. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

14. Hancock Village Inn Near Jiminy Peak

15. Secluded Family Home in Serene Stockbridge Woods

16. Treetop Hideaway in Tyringham

17. Charming, updated 3 bedroom farmhouse farm stay.

18. Leaf-Peeper Paradise in the Berkshires

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

20. Greylock Cabin

Find holiday rentals that suit your style

Top Hinsdale Hotel Reviews

Vacation Village in the Berkshires

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

FairBridge Inn Express

Jiminy Peak Mountain Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Hinsdale

Hinsdale Holiday Homes information

Explore a world of travel with Expedia