Chester Vacation Rentals

1-42 of 77 rentals

USA Vermont Chester

Greenberry North

$114 - $559 per night

3D Tour

2 Bed | 2 Bath | Sleeps 8

Hawk Pond Lodge

$153 - $751 per night

3D Tour

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

Long Trail-427N

$113 - $907 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Lakeside Elegance

$122 - $984 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 10

Easy Living

$118 - $625 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Brookhaven C4

$133 - $671 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Bear Hill Views

$114 - $722 per night

3D Tour

4 Bed | 2 Bath | Sleeps 10

Ski Mountain Townhouse

$132 - $638 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Pleasant Street 49 - First Floor

$122 - $636 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Vantage Point #41

$102 - $907 per night

3D Tour

2 Bed | 2 Bath | Sleeps 5

Hall's All-Seasons Lake House

$183 - $898 per night

3D Tour

2 Bed | 2 Bath | Sleeps 9

Sherwood Escape

$89 - $479 per night

3D Tour

Londonderry, VT

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

Cozy in Cavendish

$179 - $631 per night

3D Tour

3 Bed | 2 Bath | Sleeps 12

Brookhaven F3

$144 - $600 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Ledgewood A4

$133 - $890 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Sherman Log House

$115 - $773 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Andover Retreat

$168 - $980 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Amato Carriage House, Upper Level

$94 - $428 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Small Town Charm

$118 - $589 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Okemo Mountainside Home

$193 - $631 per night

3D Tour

5 Bed | 2.5 Bath | Sleeps 12

Brookhaven B3

$136 - $712 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

32 The Green

$110 - $258 per night

3D Tour

3 Bed | 3 Bath | Sleeps 8

Sweet Rustic Dreams

$149 - $1,514 per night

3D Tour

Bridgewater Corners, VT

5 Bed | 3 Bath | Sleeps 16

Okemo Trailside 6A

$135 - $907 per night

3 Bed | 2 Bath | Sleeps 10

A Touch of Home

$71 - $332 per night

3D Tour

0 Bed | 1 Bath | Sleeps 4

In The Trees

$140 - $854 per night

3D Tour

5 Bed | 2 Bath | Sleeps 10

Charming Victorian - 2nd Floor

$114 - $354 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Mount Holly Home

$120 - $506 per night

3D Tour

Mount Holly, VT

4 Bed | 3 Bath | Sleeps 8

Okemo Trailside 34C

$113 - $1,088 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

South Hill Lodge

$118 - $726 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Ludlow Landing

$184 - $1,207 per night

3D Tour

5 Bed | 3 Bath | Sleeps 16 (10 Adults Max)

Country Comfort Retreat

$114 - $616 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Winterplace G101

$138 - $788 per night

3D Tour

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

Birch Landing #16

$114 - $298 per night

3D Tour

4 Bed | 3 Bath | Sleeps 11

Stratton Woods

$94 - $544 per night

3D Tour

West Wardsboro, VT

2 Bed | 1 Bath | Sleeps 4

Okemo Trailside 21A

$159 - $1,351 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Place of Peace and Quiet

$139 - $1,130 per night

3D Tour

Brownsville, VT

5 Bed | 3.5 Bath | Sleeps 10

Ludlow's Gem

$92 - $447 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

West Windsor Retreat

$106 - $343 per night

3D Tour

West Windsor, VT

3 Bed | 2.5 Bath | Sleeps 6

Stratton Mountain Sanctuary

$97 - $859 per night

3D Tour

2 Bed | 2 Bath | Sleeps 7

Amherst Lake Cozy Cottage

$89 - $442 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 6

Okemo Trailside 23B, Lower Level

$80 - $538 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

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