Check in
Check out
1 guest
Filters
Map
Chester Vacation Rentals
1-24 of 142 rentals

Country Riverside Retreat

$242 avg / night (excludes fees and taxes)
Chester, VT
4.0 (4)
2 Bedrooms | 2 Bath | Sleeps 6

Log Cabin with a View

$303 avg / night (excludes fees and taxes)
Andover, VT
4.67 (21)
3 Bedrooms | 3 Bath | Sleeps 8

Mountain View Getaway

$209 avg / night (excludes fees and taxes)
North Springfield, VT
4.35 (26)
2 Bedrooms | 2 Bath | Sleeps 8

Turner Hill Cottage

$357 avg / night (excludes fees and taxes)
NEW!
Grafton, VT
4 Bedrooms | 2 Bath | Sleeps 8

A1 at Castle Hill - Apartment

$172 avg / night (excludes fees and taxes)
Cavendish, VT
4.5 (10)
1 Bedrooms | 1 Bath | Sleeps 4

A1 at Castle Hill - Townhome

$247 avg / night (excludes fees and taxes)
Cavendish, VT
4.9 (10)
2 Bedrooms | 3 Bath | Sleeps 6

Cozy in Cavendish

$257 avg / night (excludes fees and taxes)
Cavendish, VT
4.41 (17)
3 Bed | 2 Bath | Sleeps 13 (8 Adults Max)

Rivers Bend Retreat

$457 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
3.0 (2)
3 Bedrooms | 3.5 Bath | Sleeps 8

Hidden Gem

$145 avg / night (excludes fees and taxes)
Cavendish, VT
2.4 (5)
3 Bedrooms | 1 Bath | Sleeps 6

A1 at Castle Hill

$404 avg / night (excludes fees and taxes)
NEW!
Cavendish, VT
5.0 (1)
3 Bedrooms | 6 Bath | Sleeps 10

Vermont Farm Studio

$82 avg / night (excludes fees and taxes)
Proctorsville, VT
3.83 (23)
0 Bedrooms | 1 Bath | Sleeps 3

Castle Hill Condos - L4

$278 avg / night (excludes fees and taxes)
Proctorsville, VT
4.3 (30)
3 Bed | 3.5 Bath | Sleeps 9 (8 Adults Max)

Proctorsville Paradise

$148 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (8)
2 Bedrooms | 1 Bath | Sleeps 4

Castle Hill Condos O2

$280 avg / night (excludes fees and taxes)
Proctorsville, VT
4.62 (16)
3 Bed | 3.5 Bath | Sleeps 14 (8 Adults Max)

Cozy Mountain Getaway

$204 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (9)
2 Bedrooms | 1 Bath | Sleeps 5

Ski Ya Soon

$214 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
5.0 (2)
3 Bedrooms | 2 Bath | Sleeps 8

Ski Ya Later

$150 avg / night (excludes fees and taxes)
Proctorsville, VT
4.6 (5)
3 Bedrooms | 1 Bath | Sleeps 6

North Country 6

$244 avg / night (excludes fees and taxes)
NEW!
Proctorsville, VT
3 Bedrooms | 2 Bath | Sleeps 8

Vermont Farm House and Studio

$302 avg / night (excludes fees and taxes)
Proctorsville, VT
3.0 (2)
4 Bedrooms | 3 Bath | Sleeps 10

Vermont Farmhouse

$191 avg / night (excludes fees and taxes)
Proctorsville, VT
5.0 (5)
4 Bedrooms | 2 Bath | Sleeps 7

Depot Street Condo

$148 avg / night (excludes fees and taxes)
Proctorsville, VT
4.11 (9)
3 Bedrooms | 1 Bath | Sleeps 5

Magic Birch Lodge

$160 avg / night (excludes fees and taxes)
Windham, VT
4.24 (21)
2 Bedrooms | 1 Bath | Sleeps 5

Wish Upon A Star

$404 avg / night (excludes fees and taxes)
NEW!
Windham, VT
4 Bedrooms | 3.5 Bath | Sleeps 8

The Koliba

$195 avg / night (excludes fees and taxes)
NEW!
Windham, VT
1 Bedrooms | 1 Bath | Sleeps 4
Page 1 of 6
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5