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 / 26

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

  • 4
  • 8
  • 2 nights min

$501

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 / 24

Sleek 4BR West Dover House w/Private Sauna!

  • 4
  • 8
  • Min stay varies

$350

Details

1 / 22

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

  • 3
  • 8
  • Min stay varies

$150

Details

1 / 23

Apartment walking distance to Mass MoCa!!

  • 2
  • 10
  • Min stay varies

$155

Details

1 / 9

CH #B55 B055-02

  • 3
  • 7
  • 1 night min

$176

Details

1 / 44

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

  • 3
  • 10
  • Min stay varies

$114

Details

1 / 31

Classic, dog-friendly cabin in the woods w/ private deck

  • 3
  • 10
  • Min stay varies

$87

Details

1 / 30

Spacious townhome w/ easy ski access, close to hiking, golf & more!

  • 3
  • 8
  • Min stay varies

$109

Details

1 / 33

Spacious home w/ ski bus access, 2 miles from Mount Snow!

  • 3
  • 12
  • 2 nights min

$149

Details

1 / 29

Lovely townhome w/ private hot tub & decks, close to skiing!

  • 3
  • 8
  • Min stay varies

$155

Details

1 / 16

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

  • 3
  • 10
  • 2 nights min

$401

Details

1 / 25

Condo on Haystack/Hermitage Ski Mountain

  • 3
  • 8
  • 2 nights min

$250

Details

1 / 10

CH #488 488-01

  • 5
  • 12
  • 1 night min

$497

Details

1 / 13

Mountain Ski house between Stratton & MT Snow

  • 3
  • 8
  • 2 nights min

$250

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 / 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 / 23

5 miles from Mt Snow, direct VAST access!

  • 4
  • 9
  • Min stay varies

$150

Details

1 / 13

Cozy Lakefront Cottage

  • 3
  • 6
  • 3 nights min

$150

Details

1 / 13

Mount Snow Area Home with 5 Bedrooms

  • 5
  • 12
  • 2 nights min

$300

Details

1 / 9

MT SNOW NEW SKI HOME MONTHLY or SEASON 1.1 TO Mtn

  • 2
  • 4
  • 21 nights min

$150

Details

1 / 24

Country Farmhouse with Views

  • 4
  • 8
  • Min stay varies

$320

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 / 4

Golden Triangle in the Berkshires

  • 2
  • 4
  • 2 nights min

$2500

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$71

Details

1 / 19

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

  • 2
  • 6
  • Min stay varies

$100

Details

1 / 22

Contemporary Log Home - Little Creek Cabin

  • 3
  • 10
  • 2 nights min

$396

Details

1 / 63

HUGE MANSION: GREAT FOR GROUPS: SLEEP 34, 15 bedrms, 14 baths, WEDDING, RETREATS

  • 14
  • 34
  • Min stay varies

$1496

Details

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