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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Unique, fun riverfront cottage
SUPERHOST
Entire residential home · 4 guests · 4 beds · 1 bath

Unique, fun riverfront cottageOur guesthouse is on the Connecticut River in the treasured small town of Chester, half-way between New York and Boston – a little over two hours from each city and 45 minutes from New Haven and Hartford. The cottage features a wide porch, private front yard overlooking the river; a living room with a couch that pulls out to sleeps two comfortably, a dining area and kitchen at one end with a dishwasher. There's a bedroom with a queen-sized bed and a good-sized bathroom with tub and shower. A loft has two single beds, most suitable for children over 10 and younger adults. The house, on our four-acre property, is private and quiet and about two miles from the center of the village which is well-appointed with wonderful restaurants, a professional theater, galleries and one-of-a-kind shops. There is endless hiking and kayaking possibilities with a boat launch ramp adjacent to the property. Theater, music and a variety of activities and things to do are all close by. The cottage is $130 a night; $700 a week or $2500 a month. During January and February, March and April the price is $110 a night; $660 a week and $1700 a month. We’d love to have you stay.

Brand new cottage "Beriozka" on Cedar Lake
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bath

Brand new cottage "Beriozka" on Cedar LakeOriginally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Chester Village 'Pied-à-terre' above art gallery
SUPERHOST
Entire rental unit · 5 guests · 2 beds · 1 bath

Chester Village 'Pied-à-terre' above art galleryRecently renovated! If finding a place in an ideal location with thoughtful design matters to you, then you've found it! Sunlit filled living room with high ceilings, private bedroom in the back with large private deck over Pattaconk Brook. Located in the heart of Chester Village, above our art gallery & boutique, neighbor to some of the BEST restaurants in CT! Chester is renown for its art, cool shops & great food. Our place is a gem & primarily set up for the comfort of our guests.

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Popular amenities for Chester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chester

  1. Entire guest suite
  2. Essex
The Shoreham Guesthouse.
SUPERHOST
  1. Entire residential home
  2. Chester
Stunning Artisan Waterfall Escape, Walk Downtown
  1. Entire rental unit
  2. Deep River
Loft apartment, deck and great water view
  1. Entire rental unit
  2. Chester
The Millhouse Downtown Chester
SUPERHOST
  1. Private room
  2. Chester
Comfy Artist View at Chester Village
  1. Entire rental unit
  2. Essex
Entire apartment located downtown beautiful Essex
No reviews yet
  1. Entire residential home
  2. Essex
NEW! Historic Home w/ Large Yard Near Dwtn Essex!
SUPERHOST
  1. Entire residential home
  2. Haddam
Summer on the Connecticut River 4 Season Cottage
  1. Entire cabin
  2. East Haddam
Annie's Place. Cottage on Horse/Animal/Rescue Farm
SUPERHOST
  1. Entire residential home
  2. Deep River
Modern Unique Riverview Hillside Home ★★★Views!
  1. Entire rental unit
  2. Deep River
Flat on the River
SUPERHOST
  1. Entire residential home
  2. Chester
Chester Cottage Waterfall House

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