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137 Houses

23

LAKEFRONT HOME IN BERKSHIRES

Massachusetts / Berkshire

Berkshire house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$402

Price per night from

$402

Great rentals within 20 miles that match your search

Distance approx 14.55 km from Berkshire

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

$251

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$251

Distance approx 18.01 km from Berkshire

(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

$276

Price per night from

$276

Distance approx 14.54 km from Berkshire

24

3BR Lee House w/ Easy Access to Main Street!

Berkshires / Lee

Lee house

1 10 min stay varies

  • 1 bedroom
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$241

Responds fast!
avg. 10 minutes

Price per night from

$241

Distance approx 9.17 km from Berkshire

23

The Dacha: Summer/Skiing House in the Berkshires

New York / Treadwell

Treadwell apartment

2 6 3 nights min

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

Price per night from

$231

Price per night from

$231

Distance approx 11.59 km from Berkshire

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

$376

Responds fast!
avg. 10 minutes

Price per night from

$376

Distance approx 4.1 km from Berkshire Show on Map

31

Big Beautiful 7 bedroom 3 bath hot tub pool table

Berkshires / Pittsfield

Pittsfield house

7 18 2 nights min

  • 7 bedrooms
  • sleeps 18
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$301

Price per night from

$301

Distance approx 8.98 km from Berkshire

4

The Meadow House 4 bdrm 4 bath house

New York / Stephentown

Stephentown house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$631

Price per night from

$631

Distance approx 6.01 km from Berkshire Show on Map

24

Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$185

Responds fast!
avg. 10 minutes

Price per night from

$185

Distance approx 19.67 km from Berkshire

(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 6.11 km from Berkshire Show on Map

14

Christmas in The Berkshires

Berkshires / Hancock

Hancock condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$227

Price per night from

$227

Distance approx 14.45 km from Berkshire

(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

$276

Price per night from

$276

Distance approx 14.29 km from Berkshire

(2) Excellent 

8

Cozy & Modern Home -mins from Tanglewood & Kripalu

Berkshires / West Stockbridge

West Stockbridge apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$100

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$100

Distance approx 16.12 km from Berkshire

26

3BD Newly Rennovated Contempoary Near Stockbridge

Berkshires / Stockbridge

Stockbridge house

3 6 min stay varies

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

Price per night from

$301

Price per night from

$301

Distance approx 19 km from Berkshire

(1) Excellent 

24

'Butterfly Hill' West Stockbridge Home on 3 Acres!

Berkshires / West Stockbridge

West Stockbridge house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$165

Price per night from

$165

Distance approx 13.1 km from Berkshire

(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

$301

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$301

Distance approx 12.01 km from Berkshire

(6) Excellent 

6

Retreat in the Woods

Berkshires / Savoy

Savoy house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+

Price per night from

$201

Price per night from

$201

Distance approx 17.08 km from Berkshire

(9) Very Good 

22

Flight's End-A Country Home with Babbling Brook

Massachusetts / Hawley

Hawley house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.
…see more

Price per night from

$150

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$150

Distance approx 11.35 km from Berkshire

(2) Excellent 

10

Heart of Lenox

Berkshires / Lenox

Lenox house

2 4 2 nights min

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

Price per night from

$175

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$175

Distance approx 16.82 km from Berkshire

12

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Berkshires / Lee

Lee apartment

2 6 2 nights min

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

Price per night from

$376

Price per night from

$376

Distance approx 7.78 km from Berkshire Show on Map

(1) Excellent 

34

INTERIOR DESIGNERS BOTANICAL GARDENS

Berkshires / Lenox

Lenox cottage

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$105

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$105

Distance approx 13.1 km from Berkshire

(2) Very Good 

12

Heart of the Berkshires!

Berkshires / Lenox

Lenox house

3 6 2 nights min

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

Price per night from

$226

Price per night from

$226

Distance approx 6.62 km from Berkshire Show on Map

(2) Excellent 

16

PanoramicView1000 sq ft Guest Quarters Berkshires

Berkshires / Hancock

Hancock cottage

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$146

Price per night from

$146

Distance approx 11.55 km from Berkshire

7

Berkshires Cottage Country Retreat

New York / Stephentown

Stephentown cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Private garden

Price per night from

$165

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$165

Distance approx 14.84 km from Berkshire

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

$701

Price per night from

$701

Distance approx 16.59 km from Berkshire

(36) Excellent 

20

Berkshire Farmhouse Vacation

Berkshires / West Stockbridge

West Stockbridge house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
…see more

Price per night from

$261

Price per night from

$261

Distance approx 14.51 km from Berkshire

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

$201

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$201

Distance approx 5.79 km from Berkshire Show on Map

(1) Very Good 

23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Berkshires / Hancock

Hancock condo

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$200

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$200

Distance approx 14.51 km from Berkshire

(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 9.38 km from Berkshire

(6) Excellent 

23

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

New York / Stephentown

Stephentown lodge

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$376

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$376

Distance approx 14.28 km from Berkshire

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

$176

Price per night from

$176

Distance approx 13.42 km from Berkshire

14

ROOM walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

1 8 min stay varies

  • 1 bedroom
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$101

Price per night from

$101

Distance approx 8.11 km from Berkshire Show on Map

(1) Very Good 

4

Golden Triangle in the Berkshires

Berkshires / Hancock

Hancock house

2 4 2 nights min

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

Price per night from

$2,502

Price per night from

$2,502

Distance approx 16.19 km from Berkshire

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 14.15 km from Berkshire

24

NEW! House w/ Kayak - Walk to Stockbridge Bowl!

Berkshires / Lenox

Lenox house

3 6 min stay varies

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

Price per night from

$185

Price per night from

$185

Distance approx 4.24 km from Berkshire Show on Map

25

NEW! Family Home w/Game Room - 3 Mi to Jiminy Peak

Berkshires / Hancock

Hancock house

4 20 min stay varies

  • 4 bedrooms
  • sleeps 20
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$251

Price per night from

$251

Distance approx 5.79 km from Berkshire Show on Map

8

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 18.8 km from Berkshire

(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