Chester Vacation Rentals

1-42 of 51 rentals

USA Vermont Chester

Castle Hill Condo

$181 - $1,215 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 10 (7 Adults Max)

Cozy in Cavendish

$108 - $993 per night

3D Tour

3 Bed | 2 Bath | Sleeps 12

Depot Street Condo

$89 - $522 per night

3D Tour

Proctorsville, VT

3 Bed | 1 Bath | Sleeps 5

Forested Family Fun

$159 - $1,170 per night

4 Bed | 3 Bath | Sleeps 14

Minutes from the Mountain

$174 - $1,603 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 10

Lake Rescue Retreat

$183 - $1,050 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Okemo Mountainside Home

$159 - $1,595 per night

3D Tour

5 Bed | 3.5 Bath | Sleeps 12

Pleasant Street 49 - First Floor

$89 - $676 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Small Town Charm

$89 - $719 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Amato Carriage House, Upper Level

$64 - $422 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Winterplace G101

$101 - $839 per night

3D Tour

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

Ledgewood A4

$98 - $1,064 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Brookhaven F3

$106 - $704 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Okemo Trailside 6A

$115 - $1,123 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Okemo Trailside 34C

$89 - $992 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Andover Retreat

$104 - $1,170 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Charming Victorian - 2nd Floor

$90 - $481 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Amato Carriage House, Lower Level

$71 - $185 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

Sweet Pauline Cottage

$87 - $511 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

A Touch of Home

$56 - $401 per night

3D Tour

0 Bed | 1 Bath | Sleeps 4

Mountains View Cabin

$89 - $716 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Ludlow's Gem

$74 - $455 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Sherman Log House

$101 - $823 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

South Hill Lodge

$114 - $630 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Country Comfort Retreat

$114 - $654 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Okemo Trailside 8E

$63 - $526 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 23B, Lower Level

$68 - $665 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

In The Trees

$139 - $1,105 per night

3D Tour

5 Bed | 2 Bath | Sleeps 10

Bear Hill Views

$114 - $769 per night

3D Tour

4 Bed | 2 Bath | Sleeps 10

Brookhaven B3

$89 - $757 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Ludlow Landing

$165 - $1,508 per night

3D Tour

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

Hall's All-Seasons Lake House

$146 - $1,097 per night

3D Tour

2 Bed | 2 Bath | Sleeps 9

Okemo Mountain Condo

$68 - $611 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Pleasant Street 49 - Second Floor

$89 - $676 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

The Mill #307

$49 - $485 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

Pleasant Street 31 Unit B

$105 - $460 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Greenberry North

$81 - $595 per night

3D Tour

2 Bed | 2 Bath | Sleeps 8

Charming Victorian - 1st Floor

$81 - $481 per night

3D Tour

2 Bed | 2 Bath | Sleeps 8

The Mary Lou

$116 - $497 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Brookhaven C4

$105 - $749 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Pleasant Street 31 Unit A

$105 - $473 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Pleasant Street 31 Unit C

$105 - $468 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

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