10 Best Vacation Rentals in Chester - Holiday Lettings - Cabins

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10 Vacation rentals

(2) Excellent 

10

Vacation private room in Chester

Vermont / Chester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
We have a Classic Vermont Hillside Farmhouse. There are 5 bedrooms - all rooms can accommodate two people. One room has 2 twin beds AND a double, so 4 people could share that room. There are two full bathrooms in the house, a large kitchen, large dining room and liv …see more

from $60 / night

$300 / week

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from $60 / night

13

Home rental in Chester

Vermont / Chester

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
Charming 1820 stone house, The Cairn, just off Rte 103 in a small village enclave reached by crossing the historic Bartonsville covered bridge- rebuilt after hurricane Irene. The house is surrounded by a lovely garden that reaches down to the Williams River in the back …see more

from $175 / night

$1190 / week

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Responds fast!
avg. 3 hours 58 minutes

from $175 / night

(1) Excellent 

12

Ski farmhouse to rent in Chester Depot

Chester / Chester Depot

5 14 2 nights min

  • 5 bedrooms
  • Sleeps 14
  • 2 nights min
  • Nearest beach 24 mi
  • Ski
  • Child friendly
CLASSIC VERMONT HILLTOP FARMHOUSE - 5 BEDROOMS SLEEP UP TO 12 PEOPLE. GREAT FOR FAMILY & GROUP GET TOGETHERS. SECLUDED, YET WITHIN 1 HOUR'S DRIVING DISTANCE TO 6 MAJOR SKI/RECREATIONAL AREAS – OKEMO IS 8 MILES AWAY. Private and secluded, yet less than 8 miles to th …see more

from $310 / night

$2000 / week

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from $310 / night

22

Vacation home rental

Vermont / Chester

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
The Amare Guesthouse is a relaxed and inviting recently restored Victorian home steps from downtown Chester VT. From coffee to cocktails relax on one of the large porches. Walking distance to restaurants and pubs, rivers, farms, trails, antique shops, galleries, and a …see more

from $230 / night

$1600 / week

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from $230 / night

(1) Very Good 

10

Chester Vacation b&b rental

Vermont / Chester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 19 mi
  • Child friendly
  • Air conditioning
The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks th …see more

from $119 / night

$833 / week

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from $119 / night

11

Vacation b&b in Chester

Vermont / Chester

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. …see more

from $139 / night

$973 / week

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from $139 / night

30

Chester Vacation b&b rental

Vermont / Chester

6 18 1 night min

  • 6 bedrooms
  • Sleeps 18
  • 1 night min
  • Nearest beach 19 mi
  • Child friendly
  • Air conditioning
This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is …see more

from $550 / night

$3500 - $4620 / week

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from $550 / night

19

Chester Vacation guest house rental

Vermont / Chester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Ha …see more

from $125 / night

$800 - $1500 / week

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from $125 / night

10

Vacation b&b in Chester

Vermont / Chester

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rent …see more

from $139 / night

$973 / week

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from $139 / night

10

Vacation home in Chester

Vermont / Chester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The 1843 Stone House is a pre-civil war home that is quaint and comfortable for 2 families or 3 couples. The house is full of charm while also providing modern amenities. The Chester Village green is a short walk from the house where shops and restaurants are housed i …see more

from $175 / night

$1500 / week

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from $175 / night