Chester Vacation Rentals

1-42 of 73 rentals

USA Vermont Chester

Depot Street Condo

$100 - $453 per night

3D Tour

Proctorsville, VT

3 Bed | 1 Bath | Sleeps 5

Stratton Ridge

$311 - $1,524 per night

3D Tour

4 Bed | 3 Bath | Sleeps 12

Andover Retreat

$174 - $1,131 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Brookhaven F3

$147 - $677 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Charming Victorian - 2nd Floor

$110 - $576 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Cozy in Cavendish

$170 - $760 per night

3D Tour

3 Bed | 2 Bath | Sleeps 12

Okemo Trailside 34C

$100 - $1,002 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Mount Holly Home

$150 - $716 per night

3D Tour

Mount Holly, VT

4 Bed | 3 Bath | Sleeps 8

Sherwood Escape

$89 - $512 per night

3D Tour

Londonderry, VT

3 Bed | 2 Bath | Sleeps 8 (4 Adults Max)

Sweet Rustic Dreams

$149 - $1,687 per night

3D Tour

Bridgewater Corners, VT

5 Bed | 3 Bath | Sleeps 16

A Touch of Home

$59 - $372 per night

3D Tour

0 Bed | 1 Bath | Sleeps 4

Charming Victorian - 1st Floor

$110 - $576 per night

3D Tour

2 Bed | 2 Bath | Sleeps 8

Bear Hill Views

$114 - $823 per night

3D Tour

4 Bed | 2 Bath | Sleeps 10

Brookhaven B3

$136 - $806 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Ski Mountain Townhouse

$133 - $762 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Easy Living

$134 - $680 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Moonlight View

$126 - $720 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 6

Okemo Trailside 23B, Lower Level

$78 - $597 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

South Hill Lodge

$131 - $551 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Amherst Lake Cozy Cottage

$89 - $489 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 6

Stratton Woods

$74 - $554 per night

3D Tour

West Wardsboro, VT

2 Bed | 1 Bath | Sleeps 4

Okemo Mountainside Home

$156 - $1,469 per night

3D Tour

5 Bed | 3 Bath | Sleeps 12

Lakeside Elegance

$130 - $1,123 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 10

Place of Peace and Quiet

$139 - $1,238 per night

3D Tour

Brownsville, VT

5 Bed | 3.5 Bath | Sleeps 10

Hawk Pond Lodge

$153 - $850 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 11 (8 Adults Max)

Okemo Trailside 8E

$90 - $488 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

West Windsor Retreat

$89 - $331 per night

3D Tour

West Windsor, VT

3 Bed | 2.5 Bath | Sleeps 6

Brookhaven C4

$138 - $744 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Mountains View Cabin

$95 - $727 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Piece of Peace and Quiet

$114 - $1,032 per night

Brownsville, VT

4 Bed | 2.5 Bath | Sleeps 8

Ludlow's Gem

$94 - $505 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Dorset Dreamhouse

$135 - $606 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Vantage Point #41

$114 - $957 per night

3D Tour

2 Bed | 2 Bath | Sleeps 5

The Mill #307

$68 - $471 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

Stratton Studio

$106 - $581 per night

3D Tour

0 Bed | 1 Bath | Sleeps 4

32 The Green

$93 - $646 per night

3D Tour

3 Bed | 3 Bath | Sleeps 8

Stratton Mountain Sanctuary

$106 - $906 per night

3D Tour

2 Bed | 2 Bath | Sleeps 7

In The Trees

$139 - $1,001 per night

3D Tour

5 Bed | 2 Bath | Sleeps 10

Bromley Mountain Retreat

$124 - $734 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 10

Okemo Trailside 21A

$159 - $1,544 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Serenity Dawn

$127 - $603 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Bromley Mountain Condo

$60 - $411 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

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