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112 Houses

32

Berkshire Home on Lake Garfield w/Dock & Boats

Berkshires / Monterey

Monterey house

4 12 min stay varies

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

Price per night from

$300

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$300

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

$427

Responds fast!
avg. 3 hours 33 minutes

Price per night from

$427

23

Spacious Lakeside Berkshire Home

Berkshires / Monterey

Monterey house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$400

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$400

12

Fabulous Post & Beam Berkshire Rental

Berkshires / Monterey

Monterey house

7 21 nights min

  • sleeps 7
  • 21 nights min
  • Ask about children
  • Car not necessary
  • Ask about pets

Price per night from

$179

Price per night from

$179

Great rentals within 20 miles that match your search

Distance approx 16.81 km from Monterey

(4) Excellent 

10

Great Vacation House in the Berkshires on Richmond Pond

Berkshires / Richmond

Richmond house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$186

Price per night from

$186

Distance approx 11.77 km from Monterey

5

Cozy Modern Condo for the Berkshires

Berkshires / West Stockbridge

West Stockbridge condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$250

Distance approx 8.6 km from Monterey

(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 9.66 km from Monterey

(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 3.48 km from Monterey Show on Map

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. 10 minutes

Price per night from

$110

Distance approx 12.84 km from Monterey

(4) Excellent 

10

Comfortable Farmhouse in the Berkshires

Berkshires / West Stockbridge

West Stockbridge farmhouse

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$325

Price per night from

$325

Distance approx 14.02 km from Monterey

(1) Excellent 

20

Renovated Barn

Connecticut / Taconic

Taconic house

3 6 2 nights min

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

Price per night from

$350

Responds fast!
avg. 32 minutes

Price per night from

$350

Distance approx 19.18 km from Monterey

8

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Berkshires / Hinsdale

Hinsdale house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$145

Price per night from

$145

Distance approx 14.13 km from Monterey

(17) Excellent 

31

Beautifully decorated & immaculate log chalet

New York / Hillsdale

Hillsdale log cabin

3 6 2 nights min

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

Price per night from

$175

Price per night from

$175

Distance approx 14.02 km from Monterey

(7) Excellent 

18

Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.

Berkshires / West Stockbridge

West Stockbridge house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly
“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits
…see more

Price per night from

$275

Price per night from

$275

Distance approx 9.46 km from Monterey

6

Stunning Home! 120 Acres! Amazing!

Berkshires / Great Barrington

Great Barrington house

9 16 3 nights min

  • 9 bedrooms
  • sleeps 16
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,600

Price per night from

$3,600

Distance approx 18.99 km from Monterey

(3) Excellent 

42

4 Bedroom Furnished House in Lakeville Connecticut

Connecticut / Lakeville

Lakeville house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$325

Price per night from

$325

Distance approx 10.19 km from Monterey

(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

$185

Price per night from

$185

Distance approx 11.74 km from Monterey

(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 5.79 km from Monterey

22

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Berkshires / Otis

Otis house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$600

Price per night from

$600

Distance approx 5.23 km from Monterey

(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. 1 hour 29 minutes

Price per night from

$225

Distance approx 13.5 km from Monterey

15

S. Berkshires Mountain Treehouse • Views • Privacy

Berkshires / Great Barrington

Great Barrington house

2 4 14 nights min

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

Price per night from

$186

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$186

Distance approx 8.42 km from Monterey

7

the BIG room at chestnut lodge

Berkshires / Lee

Lee b and b

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$200

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$200

Distance approx 10.26 km from Monterey

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 11.19 km from Monterey

19

One of the Finest Homes and Best location in the Berkshires

Berkshires / Stockbridge

Stockbridge house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$700

Price per night from

$700

Distance approx 11.33 km from Monterey

(1) Excellent 

24

Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

Berkshires / Stockbridge

Stockbridge cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$299

Responds fast!
avg. 13 minutes

Price per night from

$299

Distance approx 10.65 km from Monterey

(2) Excellent 

30

Tranquil 3BR Stockbridge House w/Private Deck

Berkshires / Stockbridge

Stockbridge house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$225

Responds fast!
avg. 10 minutes

Price per night from

$225

Distance approx 9.26 km from Monterey

(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 9.09 km from Monterey

24

Cozy Stockbridge Home - Walk To Golf Course!

Berkshires / Stockbridge

Stockbridge house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$210

Responds fast!
avg. 10 minutes

Price per night from

$210

Distance approx 11.4 km from Monterey

(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 9.28 km from Monterey

15

House share/room for rent

Berkshires / Lee

Lee room

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi

Price per night from

$67

Price per night from

$67

Distance approx 12.67 km from Monterey

(1) Excellent 

22

Berkshire Getaway at 'Tofu'S Retreat'

Berkshires / Alford

Alford chateau

3 6 7 nights min

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

Price per night from

$215

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$215

Distance approx 15.83 km from Monterey

12

Colebrook Dream

Connecticut / Colebrook

Colebrook house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$300

Price per night from

$300

Distance approx 8.73 km from Monterey

(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

Price per night from

$150

Distance approx 10.66 km from Monterey

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 9.13 km from Monterey

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 9.81 km from Monterey

16

Beautifully Renovated Berkshires Farmhouse

Berkshires / West Stockbridge

West Stockbridge b and b

2 4 2 nights min

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

Price per night from

$210

Price per night from

$210

Distance approx 5.16 km from Monterey

(1) Average 

15

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Berkshires / Tyringham

Tyringham villa

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$395

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$395

Distance approx 9.62 km from Monterey

(13) Excellent 

17

Serene Lakefront Cottage

Berkshires / Becket

Becket house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Peaceful country escape” Really enjoyed the stay here. Very complete driving and house directions provided by the owners, and checking in - even at a late hour - was a breeze. The house was very clean, woods and lake were beautiful. Many of the hou
…see more

Price per night from

$145

Price per night from

$145