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110 Houses

(4) Excellent 

24

Waterfront Cottage - 10 Mins to Great Barrington!

Berkshires / New Marlborough

New Marlborough cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Suitable for children age 5+

Price per night from

$180

Responds fast!
avg. 46 minutes

Price per night from

$180

24

Rustic Berkshires Cottage w/ Views of Lake Buel!

Berkshires / New Marlborough

New Marlborough cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Pet Friendly

Price per night from

$110

Responds fast!
avg. 55 minutes

Price per night from

$110

10

Country Victorian Serenity in the Berkshires

Berkshires / New Marlborough

New Marlborough house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Suitable for children age 5+
  • Private garden

Price per night from

$229

Price per night from

$229

35

Charming Private Guest Suite in Historic Village in the Berkshires

Berkshires / New Marlborough

New Marlborough studio

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min

Price per night from

$95

Price per night from

$95

17

Picturesque 19th century home on 3 private acres

Berkshires / New Marlborough

New Marlborough house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Great rentals within 20 miles that match your search

Distance approx 14.84 km from New Marlborough

(4) Excellent 

20

Escape to the Berkshires!

Berkshires / Becket

Becket house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$275

Price per night from

$275

Distance approx 17.38 km from New Marlborough

18

Mountain Views Atop Blueberry Hill on 40 Acres

New York / Austerlitz

Austerlitz house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$200

Price per night from

$200

Distance approx 11.99 km from New Marlborough

(1) Excellent 

17

Restored 1886 Eyebrow Colonial

Berkshires / Stockbridge

Stockbridge house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$214

Price per night from

$214

Distance approx 13.29 km from New Marlborough

11

Beautiful Cottage at the foot of the Berkshires

New York / Copake Falls

Copake Falls cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$175

Price per night from

$175

Distance approx 8.5 km from New Marlborough

(1) Excellent 

37

Charming 2+2 Lakeside Cottage on Best Lake in CT

Connecticut / Salisbury

Salisbury cottage

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$180

Price per night from

$180

Distance approx 14.07 km from New Marlborough

(13) Very Good 

13

Quiet Comfortable Cabin 5 Min. Walk to Lake

Berkshires / Becket

Becket house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
…see more

Price per night from

$149

Price per night from

$149

Distance approx 6.29 km from New Marlborough

24

Beautiful Lakefront Berkshire Rental

Berkshires / Monterey

Monterey house

5 6 7 nights min

  • 5 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$421

Responds fast!
avg. 3 hours 51 minutes

Price per night from

$421

Distance approx 10.17 km from New Marlborough

(2) Excellent 

24

Country Elegance in the Berkshires

Berkshires / Great Barrington

Great Barrington house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$650

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$650

Distance approx 17 km from New Marlborough

24

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Berkshires / Lenox

Lenox house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$375

Responds fast!
avg. 46 minutes

Price per night from

$375

Distance approx 10.42 km from New Marlborough

(2) Average 

27

Shaker Hill

Berkshires / Great Barrington

Great Barrington house

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$375

Responds fast!
avg. 56 minutes

Price per night from

$375

Distance approx 11.49 km from New Marlborough

(4) Very Good 

18

Lakefront Berkshires Ski/Summer House, Great Views

Berkshires / Great Barrington

Great Barrington house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$125

Price per night from

$125

Distance approx 8.06 km from New Marlborough

(4) Excellent 

30

Gem of the Berkshires, walk to downtown & lake.

Berkshires / Great Barrington

Great Barrington house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0.32 mi
  • Child Friendly
  • Air conditioning
“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b
…see more

Price per night from

$300

Price per night from

$300

Distance approx 10.31 km from New Marlborough

(1) Excellent 

10

Romantic Berkshire Cottage on Storybook Estate

Berkshires / Tyringham

Tyringham cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$225

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$225

Distance approx 11.15 km from New Marlborough

(14) Excellent 

Certificate of Excellence

55

RiverSong Suite In The Berkshires

Berkshires / North Egremont

North Egremont apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning

Certificate of Excellence

Price per night from

$189

Responds fast!
avg. 35 minutes

Price per night from

$189

Distance approx 14.82 km from New Marlborough

(2) Very Good 

12

Berkshires Spacious Comfortable Charming Farmhouse

Berkshires / Lee

Lee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
…see more

Price per night from

$300

Price per night from

$300

Distance approx 8.51 km from New Marlborough

36

Spacious Berkshires Home w/ Pool & Patio!

Berkshires / North Egremont

North Egremont house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$700

Responds fast!
avg. 46 minutes

Price per night from

$700

Distance approx 14.67 km from New Marlborough

(1) Excellent 

17

Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)

Berkshires / Stockbridge

Stockbridge cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning

Price per night from

$299

Responds fast!
avg. 13 minutes

Price per night from

$299

Distance approx 10.31 km from New Marlborough

9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

Berkshires / Tyringham

Tyringham house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$250

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$250

Distance approx 13.52 km from New Marlborough

(1) Excellent 

8

Writer's Room at Chestnut Lodge

Berkshires / Lee

Lee b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 8 mi
  • Ask about children
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$175

Distance approx 13.55 km from New Marlborough

22

Vacation Home on 10 Acres with Pool and Spa

Berkshires / Stockbridge

Stockbridge house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$750

Price per night from

$750

Distance approx 15.15 km from New Marlborough

(6) Excellent 

16

Family-friendly Cottage Near Lake, Tanglewood

Berkshires / Stockbridge

Stockbridge cottage

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$285

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$285

Distance approx 17.12 km from New Marlborough

13

Quiet Country Contemporary Home on 5 Private Acres

Connecticut / West Cornwall

West Cornwall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$405

Price per night from

$405

Distance approx 13.69 km from New Marlborough

13

Garfield House

Maine / Lee

Lee apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$175

Price per night from

$175

Distance approx 13.86 km from New Marlborough

4

Horse Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 13.84 km from New Marlborough

(1) Excellent 

10

Berkshire House Share-The Blue Room

Berkshires / Lee

Lee house

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min

Price per night from

$75

Price per night from

$75

Distance approx 12.26 km from New Marlborough

24

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Berkshires / Otis

Otis log cabin

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$101

Responds fast!
avg. 22 minutes

Price per night from

$101

Distance approx 9.39 km from New Marlborough

(1) Very Good 

14

Cozy and clean in Gt Barrington- available for October

Berkshires / Great Barrington

Great Barrington house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$150

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$150

Distance approx 19.72 km from New Marlborough

44

1790 Classic Colonial Center Hall home

Connecticut / Sharon

Sharon house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly

Price per night from

$500

Price per night from

$500

Distance approx 13.78 km from New Marlborough

4

Iris Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 8.37 km from New Marlborough

21

Private Berkshire Estate w/Pool & Tennis Court

Berkshires / Great Barrington

Great Barrington house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$575

Price per night from

$575

Distance approx 17.48 km from New Marlborough

10

The Barn at Copake Lake

New York / Craryville

Craryville barn

3 14 2 nights min

  • 3 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly

Price per night from

$599

Price per night from

$599

Distance approx 11.99 km from New Marlborough

12

Cottage on East Twin Lakes, Internet Access, A/C.

Connecticut / Salisbury

Salisbury cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$157

Price per night from

$157

Distance approx 11.88 km from New Marlborough

(1) Excellent 

20

Newly Renovated Colonial on the River! Sleeps 5-6

Berkshires / Stockbridge

Stockbridge house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$285

Price per night from

$285