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Chester Vacation Rentals
1-24 of 145 rentals

Country Riverside Retreat

$234 avg / night (excludes fees and taxes)
Chester, VT
4.0 (4)
2 Bedrooms | 2 Bath | Sleeps 6

House At Dream Barn Hollow

$100 avg / night (excludes fees and taxes)
NEW!
Chester, VT
2 Bedrooms | 2 Bath | Sleeps 6

Log Cabin with a View

$292 avg / night (excludes fees and taxes)
Andover, VT
4.67 (21)
3 Bedrooms | 3 Bath | Sleeps 8

Mountain View Getaway

$198 avg / night (excludes fees and taxes)
North Springfield, VT
4.35 (26)
2 Bedrooms | 2 Bath | Sleeps 8

Turner Hill Cottage

$321 avg / night (excludes fees and taxes)
NEW!
Grafton, VT
4 Bedrooms | 2 Bath | Sleeps 8

A1 at Castle Hill - Apartment

$163 avg / night (excludes fees and taxes)
Cavendish, VT
4.5 (10)
1 Bedrooms | 1 Bath | Sleeps 4

A1 at Castle Hill - Townhome

$242 avg / night (excludes fees and taxes)
Cavendish, VT
4.89 (9)
2 Bedrooms | 3 Bath | Sleeps 6

Hidden Gem

$138 avg / night (excludes fees and taxes)
Cavendish, VT
2.4 (5)
3 Bedrooms | 1 Bath | Sleeps 6

A1 at Castle Hill

$391 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
5.0 (1)
3 Bedrooms | 6 Bath | Sleeps 10

Rivers Bend Retreat

$455 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
3.0 (2)
3 Bedrooms | 3.5 Bath | Sleeps 8

Cozy in Cavendish

$243 avg / night (excludes fees and taxes)
Cavendish, VT
4.41 (17)
3 Bed | 2 Bath | Sleeps 13 (8 Adults Max)

North Country 6

$229 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
3 Bedrooms | 2 Bath | Sleeps 8

Proctorsville Paradise

$144 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (8)
2 Bedrooms | 1 Bath | Sleeps 4

Castle Hill Condos O2

$268 avg / night (excludes fees and taxes)
Proctorsville, VT
4.62 (16)
3 Bed | 3.5 Bath | Sleeps 14 (8 Adults Max)

Vermont Farm Studio

$79 avg / night (excludes fees and taxes)
Proctorsville, VT
3.83 (23)
0 Bedrooms | 1 Bath | Sleeps 3

Ski Ya Soon

$194 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
5.0 (2)
3 Bedrooms | 2 Bath | Sleeps 8

Castle Hill Condos - L4

$264 avg / night (excludes fees and taxes)
Proctorsville, VT
4.3 (30)
3 Bed | 3.5 Bath | Sleeps 9 (8 Adults Max)

Cozy Mountain Getaway

$203 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (9)
2 Bedrooms | 1 Bath | Sleeps 5

Ski Ya Later

$144 avg / night (excludes fees and taxes)
Proctorsville, VT
4.6 (5)
3 Bedrooms | 1 Bath | Sleeps 6

Vermont Farmhouse

$183 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (5)
4 Bedrooms | 2 Bath | Sleeps 7

Vermont Farm House and Studio

$297 avg / night (excludes fees and taxes)
Proctorsville, VT
3.0 (2)
4 Bedrooms | 3 Bath | Sleeps 10

Depot Street Condo

$151 avg / night (excludes fees and taxes)
Proctorsville, VT
4.11 (9)
3 Bedrooms | 1 Bath | Sleeps 5

Magic Birch Lodge

$156 avg / night (excludes fees and taxes)
Windham, VT
4.24 (21)
2 Bedrooms | 1 Bath | Sleeps 5

Wish Upon A Star

$388 avg / night (excludes fees and taxes)
NEW!
Windham, VT
4 Bedrooms | 3.5 Bath | Sleeps 8
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