Bennington Vacation Rentals, Vacation Home Rentals & more


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Areas near Bennington

1 / 6

Mountaintop Cabin w/Waterfront & Amazing View

  • 2
  • 6
  • 2 nights min

$176

Details

Great rentals within 20 miles that match your search

1 / 40

Whole duplex w/ multiple private hot tubs perfect for group ski trips!

  • 8
  • 27
  • Min stay varies

$227

Details

1 / 22

Contemporary Log Home - Little Creek Cabin

  • 3
  • 10
  • 2 nights min

$396

Details

1 / 19

Spacious countryside townhome w/ private hot tub - near skiing at Mount Snow!

  • 3
  • 6
  • Min stay varies

$136

Details

1 / 9

MT SNOW NEW SKI HOME MONTHLY or SEASON 1.1 TO Mtn

  • 2
  • 4
  • 21 nights min

$150

Details

1 / 25

Condo on Haystack/Hermitage Ski Mountain

  • 3
  • 8
  • 2 nights min

$250

Details

1 / 22

Mt Snow Summer Fun-Outdoor Pool, Hiking, Mtn Biking, Golfing

  • 3
  • 8
  • Min stay varies

$150

Details

1 / 18

Half-duplex w/ a fireplace - minutes from skiing, golf & more!

  • 3
  • 6
  • Min stay varies

$124

Details

1 / 16

*Basecamp* Renovated 3 Bed + Loft Townhome Close to Mt. Snow and Hermitage Club

  • 3
  • 10
  • 2 nights min

$401

Details

1 / 19

Cozy Chalet In The Pines, Only 5 Mi From Mt Snow

  • 2
  • 6
  • Min stay varies

$100

Details

1 / 16

Minutes from HERMITAGE AND MOUNT SNOW...3BR/2BTH TownHouse

  • 3
  • 6
  • 2 nights min

$295

Details

1 / 23

Lakeside Year Round Totally Renovated Home

  • 5
  • 10
  • 2 nights min

$600

Details

1 / 10

Sweet Berkshire Getaway

  • 2
  • 3
  • 2 nights min

$196

Details

1 / 9

Lovely Mt Snow Condo

  • 2
  • 7
  • 1 night min

$226

Details

1 / 17

CH #274 274-01

  • 3
  • 6
  • 1 night min

$201

Details

1 / 40

Great for Groups! Sleep 20: 6.5 bedroom, 6.5 baths 30 acres Pool, tennis, dogs

  • 7
  • 20
  • Min stay varies

$625

Details

1 / 26

4 minutes from The Hildene Estate and the Equinox Resort - 58 Five Star Reviews

  • 4
  • 8
  • 2 nights min

$501

Details

1 / 33

Spacious ski house with a private hot tub, game room, and a great location!

  • 4
  • 15
  • Min stay varies

$140

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$71

Details

1 / 7

CH #25 25-02

  • 3
  • 8
  • 1 night min

$174

Details

1 / 23

5 miles from Mt Snow, direct VAST access!

  • 4
  • 9
  • Min stay varies

$150

Details

1 / 10

CH #488 488-01

  • 5
  • 12
  • 1 night min

$497

Details

1 / 7

CH #C230 C230-03

  • 3
  • 7
  • 1 night min

$149

Details

1 / 10

CH #603 603-01

  • 3
  • 8
  • 1 night min

$201

Details

1 / 10

CH #210 210-02

  • 3
  • 7
  • 1 night min

$176

Details

1 / 39

Massive ski chalet with private hot tubs and sauna perfect for mountain getaway!

  • 6
  • 24
  • Min stay varies

$233

Details

1 / 21

New Lakefront Cedar Log Home

  • 3
  • 12
  • 2 nights min

$450

Details

1 / 38

James Gandolfini Stayed Here! Rustic 5BR Mount Snow Farmhouse on 120 Private

  • 5
  • 10
  • 2 nights min

$401

Details

1 / 26

Duplex for two families w/ hot tub, balcony & fireplaces - close to Mount Snow!

  • 6
  • 12
  • Min stay varies

$216

Details

1 / 4

Golden Triangle in the Berkshires

  • 2
  • 4
  • 2 nights min

$2500

Details

1 / 13

Cozy Lakefront Cottage

  • 3
  • 6
  • 3 nights min

$150

Details

1 / 13

Mountain Ski house between Stratton & MT Snow

  • 3
  • 8
  • 2 nights min

$250

Details

1 / 13

Mount Snow Area Home with 5 Bedrooms

  • 5
  • 12
  • 2 nights min

$300

Details

1 / 24

Country Farmhouse with Views

  • 4
  • 8
  • Min stay varies

$320

Details

1 / 25

Cozy townhome w/ private hot tub, surrounded by trees, close to skiing and golf!

  • 3
  • 12
  • Min stay varies

$145

Details

1 / 24

Amazing House near Mt. Snow with Hot Tub. Sleeps 11

  • 4
  • 11
  • Min stay varies

$351

Details

1 / 4

MT SNOW 1/2 mile from MTN - Shuttle to / SKI home

  • 3
  • 9
  • 2 nights min

$450

Details

1 / 24

Sleek 4BR West Dover House w/Private Sauna!

  • 4
  • 8
  • Min stay varies

$350

Details

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