Middlebury Vacation Home Rentals, Treehouses & more


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Areas near Middlebury

1 / 13

Far Enough, an Old World Vermont Estate

  • 5
  • 10
  • 2 nights min

$351

Details

Great rentals within 20 miles that match your search

1 / 32

Bridges Resort condo w/ 3 shared pools, tennis, hot tubs, sauna, & more!

  • 2
  • 6
  • Min stay varies

$150

Details

1 / 44

Bridges Resort condo w/ shared pools, hot tub, tennis courts, gym - near skiing

  • 2
  • 6
  • Min stay varies

$71

Details

1 / 22

True ski on, ski off cozy Sugarbush condo

  • 1
  • 4
  • 2 nights min

$250

Details

1 / 8

Stay at Sugarbush! $2100 a week.

  • 3
  • 9
  • 7 nights min

$351

Details

1 / 24

New Sugarbush Post & Beam Home, Family-Friendly & More. 1/4 mile to Mtn.

  • 3
  • 11
  • Min stay varies

$425

Details

1 / 41

Bridges Resort condo w/ 3 shared pools, gym, tennis, & more. Near ski slopes!

  • 3
  • 6
  • Min stay varies

$82

Details

1 / 12

Cozy, Scenic, Lake Champlain Cottage-Charlotte, VT

  • 3
  • 6
  • 3 nights min

$300

Details

1 / 33

Alpine escape with 3 shared pools, hot tub, tennis, fitness & game room!

  • 2
  • 6
  • Min stay varies

$71

Details

1 / 10

The Farm On Mad River

  • 4
  • 8
  • 2 nights min

$501

Details

1 / 33

Inviting condo w/ 3 shared pools, hot tub, tennis, & fun-filled game room

  • 3
  • 10
  • Min stay varies

$85

Details

1 / 38

Cheerful condo w/ balcony & shared pools, hot tub, and tennis - close to skiing!

  • 3
  • 8
  • Min stay varies

$81

Details

1 / 14

Sugarbush Mad River Ski Season Vacation Rental

  • 1
  • 4
  • 2 nights min

$150

Details

1 / 11

Elmtucket on the shores of Lake Champlain

  • 6
  • 12
  • Min stay varies

$321

Details

1 / 32

Private Green Mountain get-away with pond

  • 3
  • 6
  • Min stay varies

$300

Details

1 / 9

Comfortable Sugarbush retreat w/ mountain views

  • 1
  • 3
  • 30 nights min

$30

Details

1 / 18

Condo on Sugarbush Resort shuttle route w/ a shared pool!

  • 1
  • 4
  • Min stay varies

$61

Details

1 / 28

Cozy condo w/ 3 shared pools, shared tennis & hot tubs - near the slopes, golf!

  • 1
  • 4
  • Min stay varies

$61

Details

1 / 24

Breathtaking New Lake Champlain Beach,Ski Escape!

  • 1
  • 2
  • Min stay varies

$201

Details

1 / 23

Organic Farm, House, Barn Event Rental

  • 10
  • 20
  • 2 nights min

$450

Details

1 / 12

Mountainside Condo at Sugarbush Vt Walk to the Resort!

  • 1
  • 4
  • 2 nights min

$150

Details

1 / 52

Large, modern condo close to Sugarbush

  • 5
  • 9
  • 2 nights min

$376

Details

1 / 8

Lake Dunmore House

  • 2
  • 6
  • 7 nights min

$214

Details

1 / 21

Spacious Sugarbush Summit Condo

  • 3
  • 8
  • Min stay varies

$250

Details

1 / 19

Beautiful Sugarbush slopeside loft condo

  • 2
  • 6
  • 2 nights min

$245

Details

1 / 29

Vermont Sugarbush Skiing Mad River Rental

  • 3
  • 10
  • 2 nights min

$250

Details

1 / 54

River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, Family Fun

  • 5
  • 15
  • Min stay varies

$409

Details

1 / 34

Inviting alpine condo w/3 shared pools, tennis courts, game room, gym, & hot tub

  • 2
  • 9
  • Min stay varies

$71

Details

1 / 28

Spectacular Log Cabin w/ Mountain Views near Lake

  • 3
  • 10
  • Min stay varies

$329

Details

1 / 12

The perfect ski house!

  • 3
  • 7
  • 2 nights min

$326

Details

1 / 36

Bridges Resort condo w/ shared pools, hot tub, gym, tennis courts - near skiing

  • 2
  • 6
  • Min stay varies

$71

Details

1 / 36

Lovely condo w/ balcony, ski shuttle & shared hot tub, pools, tennis, gym & more

  • 3
  • 8
  • Min stay varies

$87

Details

1 / 35

Alpine escape with shared hot tub, 3 indoor/outdoor pools, fitness center, etc.!

  • 2
  • 6
  • Min stay varies

$71

Details

1 / 31

Cozy condo w/ shared pools, hot tub, tennis courts, and more in Bridges Resort!

  • 1
  • 4
  • Min stay varies

$61

Details

1 / 16

Lakefront cabin w/ deck, dock access - canoes, kayaks & more provided, dogs OK!

  • 1
  • 2
  • Min stay varies

$61

Details

1 / 10

Middlebury VT - gorgeous home

  • 4
  • 7
  • 3 nights min

$551

Details

1 / 4

Midd Home Plate

  • 3
  • 8
  • 1 night min

$275

Details

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