Chester Vacation Rentals

1-42 of 76 rentals

USA Vermont Chester

Castle Hill Condo

$180 - $558 per night

3D Tour

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

Cozy in Cavendish

$191 - $562 per night

3D Tour

3 Bed | 2 Bath | Sleeps 12

Depot Street Condo

$89 - $377 per night

3D Tour

Proctorsville, VT

3 Bed | 1 Bath | Sleeps 5

Minutes from the Mountain

$176 - $1,229 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 10

Ledgewood A4

$97 - $882 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Lake Rescue Retreat

$154 - $821 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Charming Victorian - 2nd Floor

$90 - $233 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Small Town Charm

$110 - $552 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Bear Hill Views

$114 - $677 per night

3D Tour

4 Bed | 2 Bath | Sleeps 10

Sherman Log House

$102 - $725 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

In The Trees

$139 - $829 per night

3D Tour

5 Bed | 2 Bath | Sleeps 10

Amato Carriage House, Upper Level

$70 - $421 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Pleasant Street 49 - First Floor

$91 - $596 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

South Hill Lodge

$114 - $680 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Okemo Trailside 34C

$89 - $1,003 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Sweet Pauline Cottage

$88 - $421 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Winterplace G101

$103 - $739 per night

3D Tour

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

Ludlow Landing

$149 - $1,112 per night

3D Tour

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

Okemo Mountain Condo

$61 - $470 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Andover Retreat

$176 - $901 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Okemo Mountainside Home

$158 - $621 per night

3D Tour

5 Bed | 3.5 Bath | Sleeps 12

Ludlow's Gem

$87 - $401 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Amato Carriage House, Lower Level

$67 - $205 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

The Mill #307

$49 - $401 per night

3D Tour

1 Bed | 1 Bath | Sleeps 4

Okemo Trailside 6A

$90 - $851 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

A Touch of Home

$65 - $308 per night

3D Tour

0 Bed | 1 Bath | Sleeps 4

Country Comfort Retreat

$114 - $606 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Brookhaven F3

$128 - $551 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Brookhaven B3

$103 - $667 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Hall's All-Seasons Lake House

$134 - $842 per night

3D Tour

2 Bed | 2 Bath | Sleeps 9

Okemo Trailside 8E

$69 - $513 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Mountains View Cabin

$89 - $630 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 8

Pleasant Street 49 - Second Floor

$91 - $596 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Okemo Trailside 23B, Lower Level

$60 - $504 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Okemo Pines Birch Lane #64

$495 - $809 per night

3D Tour

4 Bed | 4.5 Bath | Sleeps 8

Ludlow Treasure

$495 - $1,260 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 8

Pleasant Street 31 Unit A

$105 - $416 per night

3D Tour

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

The Mary Lou

$122 - $438 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Greenberry North

$89 - $524 per night

3D Tour

2 Bed | 2 Bath | Sleeps 8

Okemo Trailside 23C, Lower Level

$250 - $428 per night

3D Tour

1 Bed | 1 Bath | Sleeps 6

Brookhaven C4

$99 - $310 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Pleasant Street 31 Unit C

$105 - $416 per night

3D Tour

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

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