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Holiday rentals in Chester

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Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

  1. Entire cabin
  2. Chester Basin
Cozy Chester cottage on the Water.

Cozy 2 bedroom cottage right on the water, Back Harbour, Chester. Rental includes one mooring in ideal location, large deck and spectacular view. Working fireplace with wood supply. Suitable for 1 - 4 guests. Short distance from centre of charming village of Chester. 20 minute walk to yacht club.

$288 SGD per night
SUPERHOST
  1. Entire home
  2. Chester
The Whale House

The Whale House offers bright panoramic water views from every room. Centrally located in the beautiful Village of Chester steps away from marinas, eclectic restaurants, artisan shops, beach, and yacht club. Open concept with large deck to eat and enjoy the stunning views of boats sailing by. Well appointed and beautifully decorated with fireplace and comfy furniture. Three large bedrooms, 2 full baths, fully equipped chef style modern Ikea kitchen. A true place to harbour.

$394 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Marriotts Cove
Sailors’ Paradise - Stevens Cove Guest Quarters

Just steps from the wharf you'll find Stevens Cove Guest Quarters. The apartment is at ground level with a spacious deck overlooking the mooring field. The bay is dotted with boats in this very active sailing community of Chester - home to the largest keel-boat regatta in North America. Whether you are a sailor or just enjoy the water view this is the place to see boats large and small, modest and grand from May through October. The posted price includes 15% Harmonized Sales Tax.

$166 SGD per night

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Stay near Chester's top sights

Photo of SENSEA Nordic Spa
SENSEA Nordic Spa17 locals recommend
Photo of Fo'c'sle Tavern
Fo'c'sle Tavern17 locals recommend
Photo of The Rope Loft
The Rope Loft20 locals recommend

Other great holiday rentals in Chester

SUPERHOST
  1. Entire home
  2. Chester
Charming Seaside Village Home
$392 SGD per night
  1. Entire cottage
  2. Chester
Spectacular 2 Bedroom Lake House!
$428 SGD per night
SUPERHOST
  1. Entire cottage
  2. Chester
The Boathouse on Scotch Cove
$321 SGD per night
SUPERHOST
  1. Entire guest suite
  2. Chester
Chester studio, walk to Nordic Spa , Golf & More
$123 SGD per night
SUPERHOST
  1. Entire home
  2. Chester
Chester Village Getaway
$375 SGD per night
SUPERHOST
  1. Entire cottage
  2. Chester
Chester Basin Vacation Retreat Oceanfront
$482 SGD per night
  1. Entire home
  2. Chester
Charming century-old three bedroom home In Chester
$363 SGD per night
  1. Entire cottage
  2. Chester
The Barn (Chester Oceanfront)
$209 SGD per night
  1. Entire home
  2. Chester
Cozy 3-bedroom getaway in Chester!
$446 SGD per night
SUPERHOST
  1. Entire apartment
  2. Chester
The Captain's Quarters 2bedroom harbour view condo
$482 SGD per night
  1. Entire serviced apartment
  2. Chester
Chester Trail Studio Suite
$229 SGD per night
SUPERHOST
  1. Entire home
  2. Chester
Relaxed Chester home walking distance to town
$167 SGD per night
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  4. Chester