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Search results; Over 1,000 places in Chester

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Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

The home you selected

Guest favorite

Apartment in Chester

Beautiful 2 Bedrooms in Mountains w/ full kitchen

4 guests2 bedrooms4 beds2 baths

Jun 1 – 6

More

Jun 1 – 6

More

R21,202 ZAR for 5 nights

for 5 nights

Explore more homes

Top guest favorite

Barn in Chester

Inviting studio apartment above barn in Vermont

Free cancellation

Jul 5 – 10

R13,569 ZAR for 5 nights

for 5 nights

4.99 out of 5 average rating, 637 reviews

Top guest favorite

Cabin in Chester

Luxe Rustic Cabin Near Okemo

Free cancellation

Jul 20 – 25

R25,232 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 10 reviews

Guest favorite

Hotel in Chester

Quaint Queen Room & Private Bath

Free cancellation

Jun 3 – 8

R8,016 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favorite

Hotel in Chester

Private Suite in Historic Inn

Free cancellation

Jun 15 – 20

R10,209 ZAR for 5 nights

for 5 nights

4.85 out of 5 average rating, 41 reviews

Top guest favorite

Home in Chester

Vermont Charm in the 1840 Gideon Lee House

Free cancellation

Jun 11 – 16

R23,323 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 24 reviews

Superhost

Tiny home in Chester

Sage House at Camp Greenwood Vermont with Sauna

1 queen bed

Jun 1 – 6

R19,083 ZAR for 5 nights

for 5 nights

4.92 out of 5 average rating, 38 reviews

Home in Chester

Bright and spacious 3 bed/3 bath

Free cancellation

Jun 30 – Jul 5

R25,443 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favorite

Tiny home in Chester

Tiny A-Frame Rest House in Woods

Free cancellation

Jul 20 – 25

R17,556 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 22 reviews

Guest favorite

Guesthouse in Chester

Historic Carriage House-20 Min to Okemo-Magic MTN

3 queen beds

Jun 10 – 15

R18,553 ZAR for 5 nights

for 5 nights

4.92 out of 5 average rating, 178 reviews

Top guest favorite

Home in Chester

1868 Victorian Farmhouse-20 min Okemo-Magic MTN

4 queen beds

Jun 8 – 13

R23,110 ZAR for 5 nights

for 5 nights

4.91 out of 5 average rating, 95 reviews

Superhost

Room in Chester

Stay with ZachHosting for 8 years,

Charming Chester Farmhouse – Room

Apr 28 – May 3

R10,495 ZAR for 5 nights

for 5 nights

New place to stay

Home in Springfield

The Cloverdale

Free cancellation

Jun 3 – 8

R20,885 ZAR for 5 nights

for 5 nights

New place to stay

Guest favorite

Home in Springfield

Charming New England Cape

Free cancellation

Jun 16 – 21

R22,793 ZAR for 5 nights

for 5 nights

4.97 out of 5 average rating, 66 reviews

Top guest favorite

Room in Chester

Stay with MillicentInnkeeper,

Harlequin Suite at Old Town Farm Inn

Jun 1 – 6

R16,850 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 11 reviews

Guest favorite

Cottage in Chester

Quaint stone house!

Free cancellation

Jun 9 – 14

R23,704 ZAR for 5 nights

for 5 nights

4.89 out of 5 average rating, 94 reviews

Top guest favorite

Loft in Town of Rockingham

Saxtons River Studio apartment

Free cancellation

Jun 1 – 6

R13,782 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 47 reviews

Guest favorite

Tiny home in Chester

Cozy Tiny Home with Mountain View

Free cancellation

Jun 3 – 8

R19,612 ZAR for 5 nights

for 5 nights

4.92 out of 5 average rating, 12 reviews

Top guest favorite

Home in Chester

Cozy 1850 farmhouse in Stone Village of Chester

Free cancellation

Jul 20 – 25

R21,732 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 34 reviews

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