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B&Bs in Chester and Houses – Holiday Lettings - Holiday Rentals Chester

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102 Holiday homes

Chester holiday b&b rental

Chester b&b

1 bedroom / 1 bathroom / sleeps 2

1

from £112 / night

£784 / week

Holiday b&b in Chester

Chester b&b

1 bedroom / 1 bathroom / sleeps 4

from £131 / night

£916 / week

Holiday home rental

Chester house

3 bedrooms / 2 bathrooms / sleeps 6

from £216 / night

£1,504 / week

Holiday b&b in Chester

Chester b&b

1 bedroom / 1 bathroom / sleeps 5

from £131 / night

£916 / week

Chester holiday b&b rental

Chester b&b

6 bedrooms / 7 bathrooms / sleeps 18

from £518 / night

£3,295 - £4,349 / week

Home accommodation in Chester

Chester house

5 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 11 minutes

from £133 / night

£925 / week

Holiday home in Chester

Chester house

3 bedrooms / 2 bathrooms / sleeps 8

from £189 / night

£1,318 / week

Great rentals within 20 miles that match your search

Holiday home in Proctorsville

Proctorsville house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 1 minutes

from £368 / night

£2,572 / week

Holiday home in Brownsville

Brownsville house

2 bedrooms / 1 bathroom / sleeps 4

from £136 / night

£952 / week

Bondville holiday apartment rental

Bondville apartment

3 bedrooms / 3 bathrooms / sleeps 10

from £306 / night

£2,161 / week

Holiday cottage in Unity

Unity cottage

3 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 2 hours 0 minutes

from £469 / night

£3,284 - £3,481 / week

Holiday home in Ludlow

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 13 minutes

from £118 / night

£822 / week

Holiday villa with swimming pool in Reading

Reading villa

15 bedrooms / 12 bathrooms / sleeps 44

4

from £2,302 / night

£13,388 - £26,015 / week

Holiday townhouse with golf nearby in Ludlow

Ludlow townhouse

4 bedrooms / 4 bathrooms / sleeps 12

from £376 / night

£2,490 / week

Home rental in Wardsboro

Wardsboro house

3 bedrooms / 2 bathrooms / sleeps 12

from £141 / night

£987 / week

Holiday townhouse rental

Peru townhouse

4 bedrooms / 3 bathrooms / sleeps 11

from £259 / night

£1,551 - £4,017 / week

Windham holiday home rental

Windham house

5 bedrooms / 3 bathrooms / sleeps 10

3

from £79 / night

£549 / week

Mount Holly holiday b&b rental

Mount Holly b&b

3 bedrooms / 2 bathrooms / sleeps 6

12

from £97 / night

£527 - £1,055 / week

Ski home to rent in Jamaica

Jamaica house

6 bedrooms / 4 bathrooms / sleeps 16

Responds fast! avg. 1 hour 48 minutes

from £1,412 / night

£9,883 / week

Holiday log cabin rental

Mount Holly log cabin

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 12 minutes

from £85 / night

£569 / week

Ludlow holiday condo rental

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

from £518 / night

£3,624 / week

Ski home to rent in Proctorsville

Proctorsville house

8 bedrooms / 4 bathrooms / sleeps 20

4

from £377 / night

£2,636 / week

Mount Holly holiday cottage rental

Mount Holly cottage

2 bedrooms / 1 bathroom / sleeps 4

from £118 / night

£890 / week

Plymouth holiday cottage rental

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 12

from £659 / night

£4,612 / week

Holiday private room in Mount Holly

Mount Holly private room

1 bedroom / 1 bathroom / sleeps 2

from £97 / night

£527 / week

Holiday home in West Wardsboro

West Wardsboro house

4 bedrooms / 2 bathrooms / sleeps 8

3

from £283 / night

£1,883 / week

Holiday home rental

Bondville house

4 bedrooms / 3 bathrooms / sleeps 8

from £470 / night

£3,288 / week

Holiday home rental

Ludlow house

4 bedrooms / 2 bathrooms / sleeps 10

from £236 / night

£1,412 - £1,648 / week

Ludlow holiday apartment rental

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

from £71 / night

£495 / week

Cottage rental in Plymouth

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

2

from £659 / night

£4,612 / week

Ludlow holiday home accommodation

Ludlow house

5 bedrooms / 3 bathrooms / sleeps 14

3

Responds fast! avg. 2 hours 25 minutes

from £142 / night

£989 / week

Jamaica holiday townhouse rental

Jamaica townhouse

3 bedrooms / 2 bathrooms / sleeps 12

from £471 / night

£2,824 / week

Mount Holly ski log cabin to rent.

Mount Holly log cabin

5 bedrooms / 4 bathrooms / sleeps 15

from £424 / night

£2,965 / week

Ski townhouse to rent in Peru

Peru townhouse

4 bedrooms / 3 bathrooms / sleeps 8

from £278 / night

£1,944 / week

Holiday home with shared pool in West Wardsboro

West Wardsboro house

6 bedrooms / 3 bathrooms / sleeps 14

from £207 / night

£1,450 / week

Bondville ski villa to rent.

Bondville villa

4 bedrooms / 5 bathrooms / sleeps 10

from £471 / night

£3,295 / week

Stratton Mountain holiday apartment accommodation

Stratton Mountain apartment

2 bedrooms / 2 bathrooms / sleeps 5

3

Responds fast! avg. 2 hours 11 minutes

from £189 / night

£1,648 / week

Ludlow ski home to rent.

Ludlow house

3 bedrooms / 4 bathrooms / sleeps 8

from £607 / night

£4,235 - £5,553 / week

Holiday home in Peru

Peru house

6 bedrooms / 5 bathrooms / sleeps 14

from £518 / night

£2,542 / week

Holiday chalet in Ludlow

Ludlow chalet

5 bedrooms / 3 bathrooms / sleeps 14

1

from £466 / night

£3,765 / week

Viewing 40 of 102
rentals in Chester

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Chester holidays

For scenic beauty in the middle of a vibrant and historic area, consider Chester for your next holiday destination! Most of the shops and restaurants throughout Chester can be found along Main Street, but the town is small enough that anything you wish to reach can be accessed by foot.

While you're in Chester, be sure to also make time for these destinations that highlight the rich history and beautiful scenery of the area:

  • Chester Historical Society: Learn more about the town's proud history with the exhibits and artefacts found at this long-standing museum.
  • Chester Vietnam Conflict Monument: Located in the middle of downtown, this monument is dedicated to the men and women in Chester who served in the Vietnam War.
  • Play Golf: Tater Hill Golf Club is a nine-hole course that provides an afternoon of fun for all ages and skill levels.
  • Go Skiing: Nearby Okemo Mountain is considered one of the premier destinations for skiing in the entire country.

There are great events in Chester throughout the year, ranging from live performance to parties that stretch across town. Watch chainsaw carvers show off their skills at the Big Buzz Chainsaw Carving Festival in October, sample the works of over 60 local craftsmen and artisans at Chester's Fall Craft Fair in September, or watch dozens of hot air balloons soar through the sky at the Quechee Vermont Balloon Festival in May.

Whether you're looking for a picturesque condo or apartment just steps from the outdoor recreational options throughout town, or a cosy cabin with mountain views, there's a holiday rental that will put you exactly where you want to be in Chester.

If you're looking to explore the rest of Vermont, Chester is a great location to use as a base for a series of day trips. The big city of Burlington and the outdoor attractions of Stowe can both be reached within an hour by car.

Also consider