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93 Houses

17

House On Main Street

Berkshires / Williamstown

Williamstown house

4 16 2 nights min

  • 4 bedrooms
  • sleeps 16
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$573

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$573

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

$263

Price per night from

$263

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

$361

Price per night from

$361

Great rentals within 20 miles that match your search

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

$121

Price per night from

$121

Distance approx 11.16 km from Williamstown 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

$258

Price per night from

$258

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

$722

Price per night from

$722

Distance approx 19.42 km from Williamstown

17

Beautiful Cabin in a Peaceful 4 Season Resort with Club House Amenities

Vermont / Wilmington

Wilmington chalet

6 15 2 nights min

  • 6 bedrooms
  • sleeps 15
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$367

Price per night from

$367

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

$245

Price per night from

$245

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

$371

Responds fast!
avg. 38 minutes

Price per night from

$371

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

$258

Price per night from

$258

Distance approx 14.12 km from Williamstown Show on Map

(5) Excellent 

31

Berkshires Waterfront Lakehouse Sanctuary

Berkshires / Lanesboro

Lanesboro house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$224

Responds fast!
avg. 3 hours 26 minutes

Price per night from

$224

Distance approx 7.16 km from Williamstown

20

Karin's Place

Green Mountains / Bennington

Bennington house

7 30 2 nights min

  • 7 bedrooms
  • sleeps 30
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,546

Price per night from

$1,546

Distance approx 17.2 km from Williamstown

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

$458

Price per night from

$458

Distance approx 10.78 km from Williamstown Show on Map

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

$180

Price per night from

$180

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

$212

Price per night from

$212

Distance approx 14.5 km from Williamstown Show on Map

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

$189

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$189

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

$166

Price per night from

$166

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

$189

Responds fast!
avg. 9 minutes

Price per night from

$189

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

$172

Price per night from

$172

Distance approx 11.61 km from Williamstown Show on Map

(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

$287

Price per night from

$287

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

$172

Price per night from

$172

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 2 nights min

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

Price per night from

$228

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$228

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

$430

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$430

Distance approx 17.75 km from Williamstown

11

Country Farmhouse with Views

Green Mountains / Shaftsbury

Shaftsbury house

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$516

Price per night from

$516

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

$514

Price per night from

$514

Distance approx 13.07 km from Williamstown

(6) Very Good 

6

Mountaintop Cabin w/Waterfront & Amazing View

Green Mountains / Bennington

Bennington chalet

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$200

Price per night from

$200

Distance approx 5.68 km from Williamstown Show on Map

37

Meadowhurst Farm- Queen Rm 1.6 Miles from Mass MoCA

Berkshires / Clarksburg

Clarksburg room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Pet Friendly

Price per night from

$81

Price per night from

$81

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

$188

Price per night from

$188

Distance approx 19.62 km from Williamstown

10

#214: 303 Chimney Hill Rd 214-03

Vermont / Wilmington

Wilmington house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$413

Price per night from

$413

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

$2,851

Price per night from

$2,851

Distance approx 11.59 km from Williamstown Show on Map

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

$228

Price per night from

$228

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

$180

Price per night from

$180

Distance approx 19.73 km from Williamstown

10

#927: 17 Porcupine Lane 927-02

Vermont / Wilmington

Wilmington villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$584

Price per night from

$584

Distance approx 11.8 km from Williamstown Show on Map

(1) Very Good 

6

Jiminy Peak Ski Resort-Country Village's Best Unit

Berkshires / Hancock

Hancock apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 7 minutes

Price per night from

$287

Distance approx 11.1 km from Williamstown 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

$287

Responds fast!
avg. 9 minutes

Price per night from

$287

Distance approx 17.85 km from Williamstown

25

NEW! Lakefront Averill Park Home w/Patio, Fire Pit

New York / Averill Park

Averill Park cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$115

Responds fast!
avg. 9 minutes

Price per night from

$115

Distance approx 11.7 km from Williamstown Show on Map

(2) Very Good 

16

Berkshires Vacation Rental - Bentley Brook Resort Suite

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$228

Price per night from

$228

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

$298

Price per night from

$298