Chester Vacation Rentals, Houses & More


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Areas near Chester

1 / 73

Connecticut Retreat: a magical hide-away

  • 2
  • 6
  • 3 nights min

$150

Details

Great rentals within 20 miles that match your search

1 / 5

Home available for Academic Monthly or Summer week

  • 2
  • 8
  • 7 nights min

$171

Details

1 / 24

Beautiful New London Beach House with Views of Long Island Sound

  • 4
  • 9
  • Min stay varies

$351

Details

1 / 27

Perfect Estate and Location For Your Connecticut the Best

  • 5
  • 14
  • Min stay varies

$745

Details

1 / 30

Tree Fort Suite at Stony Creek Depot

  • 2
  • 4
  • 2 nights min

$226

Details

1 / 10

Private 2 Bedroom Cottage - Walk to Beach & River

  • 2
  • 5
  • 7 nights min

$229

Details

1 / 25

White Sandy Beach at your Door

  • 4
  • 11
  • 7 nights min

$569

Details

1 / 24

New! Lakefront 1BR Cottage w/ Private Beach & Dock!

  • 1
  • 2
  • Min stay varies

$145

Details

1 / 4

The Victorian Seasons Cape

  • 3
  • 6
  • 1 night min

$651

Details

1 / 21

Historic Granite House & Tavern in Scenic Jordan Village

  • 5
  • 12
  • 2 nights min

$1501

Details

1 / 12

Spacious studio near beach

  • Studio
  • 3
  • 1 night min

$71

Details

1 / 13

Soundview - Academic Rental AVAILABLE starting September! Summer 2018 is Open!

  • 4
  • 10
  • Min stay varies

$83

Details

1 / 38

Stunning Waterfront Estate on Connecticut River

  • 5
  • 10
  • Min stay varies

$401

Details

1 / 23

Walk to the town green, beach is 5 mins, dogs welcome.

  • 4
  • 8
  • 2 nights min

$351

Details

1 / 4

Waterfront property by 1801 lighthouse

  • 4
  • 4
  • 7 nights min

$387

Details

1 / 15

Charming Waterfront Beach Cottage-WOW! Sunsets

  • 4
  • 8
  • 7 nights min

$286

Details

1 / 15

Stay Above Our Antique Shop In The Ridgeview Suite

  • 2
  • 4
  • 2 nights min

$280

Details

1 / 21

Spectacular Lakefront Home

  • 4
  • 8
  • Min stay varies

$300

Details

1 / 5

The Beach Retreat Cottage

  • 3
  • 6
  • Min stay varies

$275

Details

1 / 14

Luxurious Villa At The Norwich Inn & Spa

  • 1
  • 3
  • 2 nights min

$226

Details

1 / 7

Marina Point Villas at Saybrook Point

  • 2
  • 4
  • Min stay varies

$699

Details

1 / 15

Modern 3 Bedroom 2 Bath Waterfront House with Private Beach!

  • 3
  • 6
  • 14 nights min

$470

Details

1 / 14

North Fork House with Private Beach Access

  • 4
  • 8
  • 7 nights min

$300

Details

1 / 13

Waterfront w/ Dock on Long Island Sound! August 26-31 still open! Reduced $1000!

  • 3
  • 6
  • 7 nights min

$237

Details

1 / 21

Beautiful Solar-Powered Yurt at The Sanctuary

  • 1
  • 2
  • 1 night min

$90

Details

1 / 21

Corner Home with Rights to Private Beach

  • 3
  • 7
  • 2 nights min

$376

Details

1 / 9

3 BR Charming CT shore Beach House at Black Point

  • 3
  • 7
  • 7 nights min

$201

Details

1 / 6

Beautiful French Country Cottage

  • 2
  • 5
  • 1 night min

$401

Details

1 / 14

Private bedroom in historic house on famous Starr

  • 1
  • 2
  • 2 nights min

$95

Details

1 / 24

Dream house vacation on the Long Island Sound

  • 5
  • 14
  • 14 nights min

$950

Details

1 / 17

Indian Summer and Leaf Peeper Cottage for rent on Connecticut Shoreline

  • 1
  • 4
  • 7 nights min

$85

Details

1 / 10

Unique English Country Cottage

  • 2
  • 5
  • 1 night min

$401

Details

1 / 16

Pristine Luxury Villa At The Norwich Inn & Spa

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 17

Cozy Artist decorated Cottage, walk to beach, pets Ok, exceptional environment

  • 2
  • 6
  • 1 night min

$191

Details

1 / 11

Private Beach 5 bedroom home w/in law apt

  • 5
  • 12
  • 7 nights min

$1001

Details

1 / 12

Sophisticated Villa at the Norwich Inn & Spa - Clo

  • 1
  • 3
  • 2 nights min

$226

Details

1 / 12

Luxury Waterfront Home

  • 4
  • 9
  • 3 nights min

$425

Details

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