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Chester Vacation Rentals
1-24 of 140 rentals

Country Riverside Retreat

$247 avg / night (excludes fees and taxes)
Chester, VT
4.0 (4)
2 Bedrooms | 2 Bath | Sleeps 6

Log Cabin with a View

$319 avg / night (excludes fees and taxes)
Andover, VT
4.68 (22)
3 Bedrooms | 3 Bath | Sleeps 8

Mountain View Getaway

$217 avg / night (excludes fees and taxes)
North Springfield, VT
4.35 (26)
2 Bedrooms | 2 Bath | Sleeps 8

Turner Hill Cottage

$373 avg / night (excludes fees and taxes)
NEW!
Grafton, VT
4 Bedrooms | 2 Bath | Sleeps 8

Rivers Bend Retreat

$459 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
3.0 (2)
3 Bedrooms | 3.5 Bath | Sleeps 8

Hidden Gem

$151 avg / night (excludes fees and taxes)
Cavendish, VT
2.4 (5)
3 Bedrooms | 1 Bath | Sleeps 6

A1 at Castle Hill

$422 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
5.0 (1)
3 Bedrooms | 6 Bath | Sleeps 10

A1 at Castle Hill - Apartment

$178 avg / night (excludes fees and taxes)
Cavendish, VT
4.5 (10)
1 Bedrooms | 1 Bath | Sleeps 4

Cozy in Cavendish

$265 avg / night (excludes fees and taxes)
Cavendish, VT
4.41 (17)
3 Bed | 2 Bath | Sleeps 13 (8 Adults Max)

A1 at Castle Hill - Townhome

$259 avg / night (excludes fees and taxes)
Cavendish, VT
4.9 (10)
2 Bedrooms | 3 Bath | Sleeps 6

Proctorsville Paradise

$155 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (8)
2 Bedrooms | 1 Bath | Sleeps 4

Vermont Farm Studio

$89 avg / night (excludes fees and taxes)
Proctorsville, VT
3.83 (23)
0 Bedrooms | 1 Bath | Sleeps 3

Cozy Mountain Getaway

$208 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (9)
2 Bedrooms | 1 Bath | Sleeps 5

Vermont Farmhouse

$219 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (5)
4 Bedrooms | 2 Bath | Sleeps 7

Castle Hill Condos - L4

$288 avg / night (excludes fees and taxes)
Proctorsville, VT
4.3 (30)
3 Bed | 3.5 Bath | Sleeps 9 (8 Adults Max)

Ski Ya Later

$157 avg / night (excludes fees and taxes)
Proctorsville, VT
4.6 (5)
3 Bedrooms | 1 Bath | Sleeps 6

Castle Hill Condos O2

$300 avg / night (excludes fees and taxes)
Proctorsville, VT
4.62 (16)
3 Bed | 3.5 Bath | Sleeps 14 (8 Adults Max)

Vermont Farm House and Studio

$313 avg / night (excludes fees and taxes)
Proctorsville, VT
3.0 (2)
4 Bedrooms | 3 Bath | Sleeps 10

Depot Street Condo

$156 avg / night (excludes fees and taxes)
Proctorsville, VT
4.11 (9)
3 Bedrooms | 1 Bath | Sleeps 5

North Country 6

$259 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
3 Bedrooms | 2 Bath | Sleeps 8

Ski Ya Soon

$232 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
5.0 (2)
3 Bedrooms | 2 Bath | Sleeps 8

Wish Upon A Star

$419 avg / night (excludes fees and taxes)
NEW!
Windham, VT
4 Bedrooms | 3.5 Bath | Sleeps 8

The Koliba

$200 avg / night (excludes fees and taxes)
NEW!
Windham, VT
1 Bedrooms | 1 Bath | Sleeps 4

Magic Birch Lodge

$165 avg / night (excludes fees and taxes)
Windham, VT
4.24 (21)
2 Bedrooms | 1 Bath | Sleeps 5
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