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Vacation rentals in Hinsdale, Massachusetts, United States

Berkshire Farm Sanctuary-A home of love & kindness image 1

The long and winding driveway up to the house...
Aahhh, exhale...

It's a warm, cozy, wonderful life!

Christmas ready!

Cozy up with your loved ones in front of the fire!

Berkshire Farm Sanctuary-A home of love & kindness

3 bedrooms·2 baths

Hinsdale • Massachusetts

5(42 reviews)

$ 1.500,00 USD totaal voor 3 nachten

18–21 nov 2026

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

3 bedrooms·2 baths

Richmond • Massachusetts

4.95(62 reviews)

$ 1.701,67 USD totaal voor 3 nachten

18–21 nov 2026

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths

Hancock • Massachusetts

$ 734,36 USD totaal voor 3 nachten

18–21 nov 2026

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths

Hancock • Massachusetts

$ 696,25 USD totaal voor 3 nachten

18–21 nov 2026

After a day on the slopes, head straight to John Harvard’s. Just upstairs, no driving, no cooking, just comfort, delicious food, and crackling warmth.

Just steps from the slopes, our building sits at the base of Jiminy Peak’s 45 ski trails. Ski-in/ski-out convenience all winter long.

Winter at Jiminy Peak: Slopes, Skiers & Fireside Warmth.
Ski-in/ski-out convenience meets cozy aprs-ski vibes.

Spacious bedroom/King Bed with New Mattress & Natural Light

Comfortable Open Floor Plan - Great for Long Stays!

Ski-in/Ski-out 1BR Condo at Jiminy Peak

1 bedroom·1 bath

Hancock • Massachusetts

$ 3.000,00 USD totaal voor 30 nachten

7 mrt – 6 apr 2027

View of the Property

Berkshire vacation rental in a 10,000 acres forest

3 bedrooms·2 baths

Plainfield • Massachusetts

4.85(242 reviews)

$ 1.020,30 USD totaal voor 3 nachten

18–21 nov 2026

Nestled in scenic surroundings, just a heartbeat away from outdoor adventures

Spacious and vibrant, equipped for family entertainment and relaxation

Fire pit and Adirondack chairs in the yard

Dine al fresco on our spacious patio; perfect for enjoying morning coffee outdoors or evening conversations under the warm glow of our elegantly lit covered porch, a cozy spot for nightcaps

Sleek, modern kitchen equipped with state-of-the-art appliances and a spacious layout for culinary adventures

Berkshires Escape - ski, hike, museums, and more!

4 bedrooms·2 baths

Adams • Massachusetts

4.98(61 reviews)

$200/ nacht(excl. kosten & belastingen)

Ruins of Ashintully, 1/4 mile walk up hill from the cottage

Ashintully Cottage, front view from Sodom Road.

Back view: cottage is across the street from the Ashintully Gardens.

Cottage is surrounded by land under conservation restriction, with hiking trails

Cottage is bright and filled with light from all directions.

Ashintully Cottage

4 bedrooms·3 baths

Tyringham • Massachusetts

5(45 reviews)

$ 1.426,95 USD totaal voor 3 nachten

18–21 nov 2026

7 person Artesian Grand Cayman hot tub with all the bells and whistles.

The living room has a gas fireplace, smart TV, and the couch can pull out for an extra bed for large groups.

The walk-out basement has a large screen smart TV, shuffleboard, magnetic dart board, pull-out couch, an ottoman that folds out into a single bed, a woodstove, and it all leads out to the hot tub. Free firewood is just outside the door.

Great spot to have your morning coffee and catch the morning sun.

Master bedroom with flat-screen smart TV, private bathroom including bathtub and shower, closet space, dressers, an LED wall mount fireplace, and a wall unit minisplit system for heating and cooling.

The Meadows House @ Otis Ridge w/ 7-person hot tub

3 bedrooms·2 baths

Otis • Massachusetts

4.84(204 reviews)

$ 958,87 USD $ 865,04 USD totaal voor 3 nachten

18–21 nov 2026

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Fully stocked eat-in kitchen

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath

Monterey • Massachusetts

$ 667,81 USD totaal voor 3 nachten

18–21 nov 2026

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Fully stocked eat-in kitchen

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath

Monterey • Massachusetts

$ 587,02 USD totaal voor 3 nachten

18–21 nov 2026

Condo near Mass Moca

Condo near Mass Moca

Condo near Mass Moca

Condo near Mass Moca

Condo near Mass Moca

Condo near Mass Moca

3 bedrooms·2 baths

North Adams • Massachusetts

4.83(6 reviews)

$ 1.130,00 USD totaal voor 3 nachten

18–21 nov 2026

This 3-bedroom, 2.5-bath home sits on a full acre in a quiet neighborhood, with plenty of space outside for kids to run and play.

The acre lot has plenty of room for tossing a football or a game of soccer.

Berkshires Fall Escape with Views & Cozy Fireplace image 3

Berkshires Fall Escape with Views & Cozy Fireplace image 4

Berkshires Fall Escape with Views & Cozy Fireplace image 5

Berkshires Fall Escape with Views & Cozy Fireplace

3 bedrooms·2½ baths

Great Barrington • Massachusetts

5(30 reviews)

$ 8.892,00 USD totaal voor 32 nachten

18 dec 2026 – 19 jan 2027

The Blooming Inn Front elevation summer view

Bridge of Flowers summer

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.

1 bedroom·1 bath

Shelburne Falls • Massachusetts

5(4 reviews)

$ 350,10 USD totaal voor 3 nachten

18–21 nov 2026

The Blooming Inn Front elevation summer view

Bridge of Flowers winter evening

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

1 bedroom·1 bath

Shelburne Falls • Massachusetts

4.8(5 reviews)

$ 375,77 USD totaal voor 3 nachten

18–21 nov 2026

The Blooming Inn Front elevation summer view

Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath

1 bedroom·1 bath

Shelburne Falls • Massachusetts

5(6 reviews)

$ 389,78 USD totaal voor 3 nachten

30 nov – 3 dec 2026

The Blooming Inn Front elevation summer view

Marigold queen bed with en-suite bathroom

Marigold queen bed with en-suite bathroom

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room

1 bedroom·1 bath

Shelburne Falls • Massachusetts

4.5(2 reviews)

$ 407,28 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony bedroom

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

2 bedrooms·1 bath

Shelburne Falls • Massachusetts

5(2 reviews)

$ 564,83 USD totaal voor 3 nachten

30 nov – 3 dec 2026

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

Spacious & Cozy Ground Floor 2/3 Bed private suite 5 minutes walk to the Bridge of Flowers

3 bedrooms·2 baths

Shelburne Falls • Massachusetts

$ 653,52 USD totaal voor 3 nachten

18–21 nov 2026