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141 Houses

18

Historic Home on 8.5 Acres

Berkshires / Dalton

Dalton house

3 9 3 nights min

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

Price per night from

$401

Price per night from

$401

Great rentals within 20 miles that match your search

Distance approx 15 km from Dalton

(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 5.22 km from Dalton 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 8.91 km from Dalton

(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 9.01 km from Dalton

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

$226

Price per night from

$226

Distance approx 11.06 km from Dalton

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 9.3 km from Dalton

7

"The Barn" on Tower Mountain

Berkshires / Hancock

Hancock house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min

Price per night from

$150

Price per night from

$150

Distance approx 12.48 km from Dalton

(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

$200

Price per night from

$200

Distance approx 13.64 km from Dalton

(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 5.94 km from Dalton Show on Map

(17) Excellent 

10

Stone School Cottage

Berkshires / Lanesboro

Lanesboro cottage

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden
“A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.
…see more

Price per night from

$155

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$155

Distance approx 15.84 km from Dalton

37

3 BR apartment, walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

3 15 min stay varies

  • 3 bedrooms
  • sleeps 15
  • min stay varies
  • Ski
  • Child Friendly
  • Car not necessary

Price per night from

$186

Price per night from

$186

Distance approx 9.77 km from Dalton

12

Idyllic Berkshire Home perfect for families or friends with pool and gardens

Berkshires / Richmond

Richmond house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly

Price per night from

$501

Price per night from

$501

Distance approx 19.63 km from Dalton

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

$402

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$402

Distance approx 8.63 km from Dalton

24

Vacation Village in the Berkshires

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

$157

Price per night from

$157

Distance approx 18.79 km from Dalton

(4) Excellent 

16

Lakefront Summer Vacation Cottages

Hampshire County / Goshen

Goshen cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$171

Price per night from

$171

Distance approx 16.33 km from Dalton

12

Fabulous NEW Spacious House in the Berkshires Tanglewood

Berkshires / Stockbridge

Stockbridge house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$250

Distance approx 12.04 km from Dalton

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 6.43 km from Dalton 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 11.36 km from Dalton

(1) Excellent 

13

The Gatehouse on Golden Hill

Berkshires / Lee

Lee house

4 14 3 nights min

  • 4 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$799

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$799

Distance approx 9.82 km from Dalton

(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 9.42 km from Dalton

(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 12.04 km from Dalton

(1) Excellent 

2

chestnut lodge Queens Room

Berkshires / Lee

Lee b and b

1 2 2 nights min

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

Price per night from

$146

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$146

Distance approx 12.43 km from Dalton

20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Berkshires / Richmond

Richmond house

3 6 7 nights min

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

Price per night from

$500

Price per night from

$500

Distance approx 8.79 km from Dalton

(10) Very Good 

21

Wyndham Bentley Brook at Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$251

Price per night from

$251

Distance approx 12.61 km from Dalton

(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 8.65 km from Dalton

9

Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

Berkshires / Hancock

Hancock condo

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$451

Price per night from

$451

Distance approx 15.73 km from Dalton

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

$211

Responds fast!
avg. 24 minutes

Price per night from

$211

Distance approx 19.02 km from Dalton

24

Rustic Goshen Cabin w/ Fire Pit, BBQ & Great Deck!

Hampshire County / Goshen

Goshen log cabin

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$211

Responds fast!
avg. 24 minutes

Price per night from

$211

Distance approx 14.78 km from Dalton

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

$151

Price per night from

$151

Distance approx 8.64 km from Dalton

24

Ski in Ski Out, Summer fun, Wyndham Bentley Brook

Berkshires / Hancock

Hancock condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$199

Price per night from

$199

Distance approx 14.77 km from Dalton

4

Nasturtium 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

$151

Price per night from

$151

Distance approx 8.64 km from Dalton

19

Enjoy cozy Bentley Brook for your family getaway!

Berkshires / Hancock

Hancock studio

Studio 4 3 nights min

  • Studio
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$84

Price per night from

$84

Distance approx 15.33 km from Dalton

(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 8.63 km from Dalton

67

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

Berkshires / Hancock

Hancock house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$117

Price per night from

$117

Distance approx 7.26 km from Dalton

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

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$251

Distance approx 15.33 km from Dalton

10

Sweet Berkshire Getaway

Berkshires / North Adams

North Adams house

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Nearest beach 0.5 mi
  • Private garden

Price per night from

$195

Price per night from

$195

Distance approx 14.68 km from Dalton

23

Newly Renovated Berkshire Cottage near Tanglewood

Berkshires / Lee

Lee cottage

1 2 60 nights min

  • 1 bedroom
  • sleeps 2
  • 60 nights min
  • Nearest beach 5 mi
  • Air conditioning

Price per night from

$285

Responds fast!
avg. 13 minutes

Price per night from

$285

Distance approx 16.36 km from Dalton

31

|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

Berkshires / Stockbridge

Stockbridge house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$450

Responds fast!
avg. 1 hour 31 minutes

Price per night from

$450