Questing Holiday Rentals

      Highly Rated

Cottage

Charming Cottage, New Marlborough Village Green in the Berkshires

• Great Barrington
• ·
• New Marlborough
• 1.56 mi to center

10.0

Exceptional

(77 Reviews)

2 Bedrooms 1 Bath 4 Guests 600 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£219/Night 7 Nights - £1,534

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House

Berkshire Riverfront Ski Cabin: Close to Hiking!

• Great Barrington
• ·
• New Marlborough
• 1.46 mi to center

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 5 Guests 1097.92 ft²

• 
  Parking
• 
  Internet
• 
  Pet Friendly
• 
  Sports/Activities

£280/Night 7 Nights - £1,962

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      Highly Rated

Hotel

Gedney Farm

• Great Barrington
• ·
• New Marlborough
• 1.62 mi to center

9.2

Exceptional

(139 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

£218/Night 7 Nights - £1,525

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House

Peaceful, Post and Beam Loft, Sleeps 9

• Great Barrington
• ·
• New Marlborough
• 3.95 mi to center

9.8

Exceptional

(24 Reviews)

1 Bedroom 2 Baths 9 Guests 2126 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£297/Night 7 Nights - £2,077

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      Price Dropped

House

Hilltop Escape with Views & Hot Tub

• Great Barrington
• ·
• New Marlborough
• 1.54 mi to center

3 Bedrooms 3 Baths 6 Guests 2368.06 ft²

• 
  Hot Tub
• 
  Parking
• 
  View
• 
  Air Conditioner

£302/Night 7 Nights - £2,112

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      Highly Rated

Hotel

The Old Inn On The Green

• Great Barrington
• ·
• New Marlborough
• 1.58 mi to center

9.2

Exceptional

(91 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

£293/Night 7 Nights - £2,051

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Cabin

Berkshire Riverfront Ski Cabin: Close to Hiking!

• Great Barrington
• ·
• New Marlborough
• 1.46 mi to center

9.6

Exceptional

(45 Reviews)

2 Bedrooms 1 Bath 5 Guests 1100 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£398/Night 7 Nights - £2,786

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Hotel

The Old Inn On The Green

• Great Barrington
• ·
• New Marlborough
• 1.58 mi to center

9.8

Exceptional

(12 Reviews)

11 Baths

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  View

£258/Night 7 Nights - £1,806

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House

Peaceful and Private Setting

• Massachusetts
• ·
• Sheffield
• 2.89 mi to center

10.0

Exceptional

(6 Reviews)

3 Bedrooms 3 Baths 6 Guests

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Kitchen

£550/Night 7 Nights - £3,849

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Hotel

Gedney Farm

• Great Barrington
• ·
• New Marlborough
• 1.61 mi to center

7.4

Very Good

(15 Reviews)

7 Baths

• 
  Hot Tub
• 
  Parking
• 
  Skiing
• 
  Balcony/Terrace

£221/Night 7 Nights - £1,545

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House

Cozy escape in the trees of the Berkshires

• Great Barrington
• ·
• New Marlborough
• 0.47 mi to center

10.0

Exceptional

(4 Reviews)

5 Bedrooms 2 Baths 10 Guests

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

£643/Night 7 Nights - £4,503

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House

New England Family Home with Hot Tub and Pool

• Great Barrington
• ·
• New Marlborough
• 1.97 mi to center

10.0

Exceptional

(3 Reviews)

5 Bedrooms 2 Baths 8 Guests

• 
  Private Pool
• 
  Hot Tub
• 
  Parking
• 
  Pool

£433/Night 7 Nights - £3,033

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      Price Dropped

House

Sunset Falls: A Berkshire Mountain Luxury Retreat

• Great Barrington
• ·
• New Marlborough
• 0.78 mi to center

10.0

Exceptional

(2 Reviews)

6 Bedrooms 6 Baths 12 Guests

• 
  Hot Tub
• 
  Parking
• 
  Spa
• 
  Balcony/Terrace

£3,642/Night 7 Nights - £25,492

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House

Hilltop Escape with Views & Hot Tub

• Great Barrington
• ·
• New Marlborough
• 1.54 mi to center

10.0

Exceptional

(2 Reviews)

3 Bedrooms 2 Baths 6 Guests 2370 ft²

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

£404/Night 7 Nights - £2,829

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House

Lovely vacation home on secluded hillside with views and heated pool

• Great Barrington
• ·
• New Marlborough
• 1.32 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 6 Guests

• 
  Private Pool
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

£553/Night 7 Nights - £3,873

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House

Steepletop - Nature Lovers Paradise with Rec Room

• Great Barrington
• ·
• New Marlborough
• 3.06 mi to center

9.8

Exceptional

(6 Reviews)

4 Bedrooms 2 Baths 8 Guests 3100 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Internet

£447/Night 7 Nights - £3,125

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Cottage

Pine View Cottage, Berkshires Getaway Lake Buel w/lake rights. Pet friendly!

• Great Barrington
• ·
• New Marlborough
• 4.90 mi to center

9.4

Exceptional

(28 Reviews)

3 Bedrooms 2 Baths 6 Guests

• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

£322/Night 7 Nights - £2,257

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House

Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!

• Great Barrington
• ·
• New Marlborough
• 2.96 mi to center

5 Bedrooms 4 Baths 14 Guests

• 
  Private Pool
• 
  Hot Tub
• 
  Parking
• 
  Pool

£1,252/Night 7 Nights - £8,763

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House

Beautiful Berkshire Home - in the heart of Southfield, Ma. -The Berkshires

• Great Barrington
• ·
• New Marlborough
• 0.61 mi to center

3 Bedrooms 2 Baths 6 Guests 1650 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£395/Night 7 Nights - £2,765

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New

Apartment

Cozy 1-bedroom guesthouse in beautiful Southfield

• Great Barrington
• ·
• New Marlborough
• 0.40 mi to center

1 Bedroom 1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£191/Night 7 Nights - £1,336

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Cottage

2-bedroom cottage close to hiking and swimming with AC

• Great Barrington
• ·
• New Marlborough
• 1.56 mi to center

10.0

Exceptional

(5 Reviews)

2 Bedrooms 2 Baths 4 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£261/Night 7 Nights - £1,829

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      Highly Rated

Cottage

Perfect Vacation Get Away - Historical New Marlborough

• Great Barrington
• ·
• New Marlborough
• 1.51 mi to center

9.2

Exceptional

(57 Reviews)

1 Bedroom 1 Bath 4 Guests 1200 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£182/Night 7 Nights - £1,271

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Cabin

Cosmo Cabin: Your Cozy Escape

• Great Barrington
• ·
• New Marlborough
• 1.94 mi to center

2 Bedrooms 1 Bath 3 Guests 520 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

£242/Night 7 Nights - £1,694

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House

NEW LISTING: Cozy Berkshire Cottage 15 Min From Great Barrington

• Great Barrington
• ·
• New Marlborough
• 3.44 mi to center

2 Bedrooms 1 Bath 4 Guests 900 ft²

• 
  Kitchen
• 
  Internet
• 
  Pet Friendly
• 
  Child Friendly

£183/Night 7 Nights - £1,282

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