Bennington Vacation Rentals, Vacation Home Rentals & More


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Areas near Bennington

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Mountaintop Cabin w/Waterfront & Amazing View

  • 2
  • 6
  • 2 nights min

$175

Details

Great rentals within 30 miles that match your search

1
1 / 13

Cozy Lakefront Cottage

  • 3
  • 6
  • 3 nights min

$150

Details

1 / 11

Country Farmhouse with Views

  • 4
  • 8
  • 3 nights min

$450

Details

1 / 24

Country Farmhouse with Views

  • 4
  • 8
  • Min stay varies

$300

Details

1 / 6

Beautiful Vacation Home on a Private Lake

  • 3
  • 7
  • 7 nights min

$214

Details

1 / 17

House On Main Street

  • 4
  • 16
  • Min stay varies

$446

Details

2
1 / 23

Apartment walking distance to Mass MoCa!!

  • 2
  • 10
  • Min stay varies

$155

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$70

Details

1 / 31

3 BR apartment, walking distance to Mass MoCa

  • 3
  • 15
  • Min stay varies

$165

Details

1 / 10

Sweet Berkshire Getaway

  • 2
  • 3
  • 2 nights min

$195

Details

1 / 21

Lake House in Berkshires

  • 1
  • 2
  • 2 nights min

$105

Details

1
1 / 26

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

  • 4
  • 8
  • 2 nights min

$500

Details

8
1 / 7

Berkshire Getaway

  • 2
  • 4
  • 1 night min

$150

Details

1 / 24

Cozy golf course home w/ nearby skiing, hikes, and more!

  • 4
  • 8
  • Min stay varies

$90

Details

1
1 / 13

Mount Snow Area Home with 5 Bedrooms

  • 5
  • 12
  • 2 nights min

$300

Details

5
1 / 20

Condo on Haystack/Hermitage Ski Mountain

  • 3
  • 8
  • 2 nights min

$250

Details

1 / 13

Beautiful Mountainside 2 Bedroom 2 Bath Condominium

  • 2
  • 8
  • Min stay varies

$100

Details

1 / 4

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

  • 3
  • 9
  • 2 nights min

$450

Details

5
1 / 16

Condo at Mt. Snow in So VT May 27-30 @ $145/night

  • 2
  • 8
  • 2 nights min

$145

Details

4
1 / 22

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

  • 3
  • 8
  • Min stay varies

$150

Details

1 / 17

Swiss Chalet on the Ski Trail at Mt. Snow

  • 5
  • 12
  • 2 nights min

$1750

Details

1 / 10

Luxury Ski-in, ski-out condo on Mount Snow

  • 4
  • 10
  • 2 nights min

$900

Details

1 / 29

Atmospheric cabin w/ deck, wood stove & forest views - one mile from the lifts!

  • 4
  • 8
  • 2 nights min

$107

Details

1
1 / 44

Ski-in/ski-out condo with shared pool, hot tub & sauna - great location!

  • 3
  • 10
  • Min stay varies

$118

Details

1 / 24

Sunderland Vistas, STUNNING VIEWS, Sunset decks

  • 5
  • 10
  • 2 nights min

$450

Details

1 / 8

CH #A102 A102-02

  • 3
  • 6
  • 1 night min

$175

Details

1 / 7

CH #C230 C230-03

  • 3
  • 7
  • 1 night min

$150

Details

1 / 10

CH #210 210-02

  • 3
  • 7
  • 1 night min

$175

Details

1 / 10

CH #274 274-01

  • 3
  • 7
  • 1 night min

$200

Details

1 / 9

CH #B55 B055-02

  • 3
  • 7
  • 1 night min

$175

Details

1 / 10

CH #488 488-01

  • 5
  • 12
  • 1 night min

$500

Details

1
1 / 7

CH #25 25-02

  • 3
  • 8
  • 1 night min

$175

Details

1 / 10

CH #603 603-01

  • 3
  • 8
  • 1 night min

$200

Details

1 / 27

Cozy condo near the slopes w/shared hot tub, pool, fitness & more!

  • 2
  • 6
  • Min stay varies

$91

Details

1 / 16

Balsam Cottage 4BR, Hot Tub, Pool Table, Fireplace - 5 minutes to the slopes

  • 4
  • 10
  • 2 nights min

$300

Details

1 / 11

Beautiful 3 Bedroom Home at Mount Snow

  • 3
  • 8
  • 2 nights min

$200

Details

1 / 39

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

  • 6
  • 24
  • Min stay varies

$126

Details

1 / 26

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

  • 6
  • 12
  • Min stay varies

$119

Details

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