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92 Houses

17

House On Main Street

Berkshires / Williamstown

Williamstown house

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$501

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$501

6

Thanksgiving week lux condo/4 Berkshires

Berkshires / Williamstown

Williamstown condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$227

Price per night from

$227

9

Cozy farmhouse, walk to campus & town

Berkshires / Williamstown

Williamstown house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$316

Price per night from

$316

Great rentals within 20 miles that match your search

Distance approx 15.48 km from Williamstown Show on Map

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

$626

Price per night from

$626

Distance approx 4.28 km from Williamstown Show on Map

(2) Excellent 

41

Apartment walking distance to Mass MoCa!!

Berkshires / North Adams

North Adams apartment

2 10 min stay varies

  • 2 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Car not necessary

Price per night from

$174

Price per night from

$174

Distance approx 16.21 km from Williamstown 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 11.72 km from Williamstown Show on Map

(3) Very Good 

14

2200sf Country House on 16 Acres-2 Miles to Jiminy

Berkshires / Hancock

Hancock house

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
…see more

Price per night from

$226

Price per night from

$226

Distance approx 6.03 km from Williamstown Show on Map

(1) Excellent 

21

Lake House in Berkshires

Berkshires / North Adams

North Adams cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$105

Price per night from

$105

Distance approx 11.6 km from Williamstown Show on Map

20

Experience The Great Outdoors At Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$107

Price per night from

$107

Distance approx 11.79 km from Williamstown 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

$186

Responds fast!
avg. 22 minutes

Price per night from

$186

Distance approx 15.87 km from Williamstown Show on Map

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

$151

Price per night from

$151

Distance approx 19.67 km from Williamstown

38

'John's Farmhouse in Mount Snow' on 120 Acres!

Vermont / Whitingham

Whitingham house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$325

Responds fast!
avg. 34 minutes

Price per night from

$325

Distance approx 11.72 km from Williamstown 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

$156

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$156

Distance approx 12.08 km from Williamstown

6

Beautiful Vacation Home on a Private Lake

New York / Petersburg

Petersburg house

3 7 7 nights min

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

Price per night from

$212

Price per night from

$212

Distance approx 4.54 km from Williamstown Show on Map

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 11.77 km from Williamstown

(8) Excellent 

7

Berkshire Getaway

Berkshires / North Adams

North Adams cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly
“peace and quiet!” This cottage is in a private, peaceful setting. We very much enjoyed our stay. We spent time at the Mass. Museum of Contemporary art in nearby North adams. We visited the summit of Mount Greylock, which was beautiful. We found our ho
…see more

Price per night from

$151

Price per night from

$151

Distance approx 19.85 km from Williamstown

(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

$149

Responds fast!
avg. 2 hours 10 minutes

Price per night from

$149

Distance approx 11.76 km from Williamstown Show on Map

13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Berkshires / Hancock

Hancock condo

2 7 2 nights min

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

Price per night from

$220

Price per night from

$220

Distance approx 11.76 km from Williamstown Show on Map

(1) Excellent 

13

Jiminy Peak Luxury Ski In/Ski Out Home

Berkshires / Hancock

Hancock condo

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$390

Price per night from

$390

Distance approx 13.36 km from Williamstown

(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 11.71 km from Williamstown 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 10.8 km from Williamstown Show on Map

(1) Excellent 

26

Whitman Woods - A Berkshire Vacation

Berkshires / Hancock

Hancock house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Private garden

Price per night from

$100

Price per night from

$100

Distance approx 11.59 km from Williamstown Show on Map

(1) Very Good 

23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Berkshires / Hancock

Hancock condo

2 6 min stay varies

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

Price per night from

$129

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$129

Distance approx 14.01 km from Williamstown

(1) Excellent 

13

Cozy Lakefront Cottage

Vermont / Somerset

Somerset cottage

3 6 3 nights min

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

Price per night from

$151

Price per night from

$151

Distance approx 19.27 km from Williamstown

24

Wilmington Home w/Pool Access- 20 Mins to Mt. Snow

Vermont / Wilmington

Wilmington house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$164

Responds fast!
avg. 10 minutes

Price per night from

$164

Distance approx 12.18 km from Williamstown

15

Little Bit of Heaven

Green Mountains / Readsboro

Readsboro house

3 6 2 nights min

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

Price per night from

$99

Responds fast!
avg. 37 minutes

Price per night from

$99

Distance approx 15.33 km from Williamstown Show on Map

(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

$373

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$373

Distance approx 17.71 km from Williamstown

(16) Very Good 

27

Berkshire house w/ fireplace, A/C, WiFi & laundry

Hampshire County / Plainfield

Plainfield house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Ski
“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.
…see more

Price per night from

$205

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$205

Distance approx 13.19 km from Williamstown Show on Map

13

Berkshires Summer Rental Beaver Pond Hancock MA

Berkshires / Hancock

Hancock condo

3 6 30 nights min

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

Price per night from

$100

Price per night from

$100

Distance approx 7.68 km from Williamstown Show on Map

38

Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Berkshires / Adams

Adams house

7 14 2 nights min

  • 7 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$401

Price per night from

$401

Distance approx 11.7 km from Williamstown Show on Map

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 13.79 km from Williamstown

20

Romantic Waterfront Vermont Cottage

Bennington / North Bennington

North Bennington house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$165

Price per night from

$165

Distance approx 8.56 km from Williamstown 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

$2,483

Price per night from

$2,483

Distance approx 11.16 km from Williamstown Show on Map

10

Vacation Village in the Berkshires Available July 22-29

Berkshires / Hancock

Hancock condo

2 8 7 nights min

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

Price per night from

$156

Price per night from

$156

Distance approx 19.35 km from Williamstown

29

Charming 'Swiss Chalet' Ski Cabin Near Mount Snow

Vermont / Wilmington

Wilmington house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly

Price per night from

$176

Price per night from

$176

Distance approx 19.59 km from Williamstown

12

Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access

Vermont / Wilmington

Wilmington house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$186

Price per night from

$186

Distance approx 8.28 km from Williamstown Show on Map

68

The Lodge at Fox Hollow

New York / Petersburg

Petersburg house

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$261

Price per night from

$261

Distance approx 11.6 km from Williamstown Show on Map

19

Find outdoor adventure at Jiminy Peak mountain!

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