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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.

Squid Cove Cottage on ocean
SUPERHOST
Entire cottage · 2 guests · 1 bed · 1 bathroom

Squid Cove Cottage on oceanRomantic getaway on oceanfront. Minutes from the village of Chester and 30 minutes to Halifax. Beaches near by, short drive to Mahone Bay, Lunenburg and other tourist attraction like Oak Island. Only 5 minutes from the Nordic Spa.

Charming Seaside Village Home
Entire residential home · 8 guests · 4 beds · 1 bathroom

Charming Seaside Village HomeWelcome to Sailors Rest! A beautiful, fully-renovated early 19th century seaside home in sought after Chester, NS. Located in the heart of the village, the magic of this seaside location awaits you. The 26-foot deck provides full sunlight for most of the day, with plenty of room to enjoy beautiful summer days and evenings. Come stay at Sailors Rest, and enjoy a day on the ocean or the classic 18- hole golf course in a seaside setting. Let Sailors Rest be your home away from home.

The Barn (Chester Oceanfront)
Entire cottage · 4 guests · 3 beds · 1 bathroom

The Barn (Chester Oceanfront)The 200+ year old converted barn is on the ocean 5 minutes from the village of Chester. The Barn offers the perfect get away to recharge in peace and quiet or an easy launch pad for everything the South Shore has to offer. Wake up to views of the ocean. Enjoy your coffee on the deck. Walk down to the beach and have a morning dip (if you dare!). Ideal for families with lots of space to explore. We live in a separate house on the property and are here to help make your stay enjoyable!

Holiday rentals for every style

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Popular amenities for Chester holiday rentals

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

Other great holiday rentals in Chester

  1. Entire residential home
  2. Chester
The Whale House
  1. Entire residential home
  2. Chester
60' Lap Pool - Steps to Ocean - 5 min walk to town
SUPERHOST
  1. Entire cottage
  2. Chester
The Boathouse on Scotch Cove
  1. Entire cottage
  2. Chester
New Listing! Ocean Front access from Cottage.
  1. Entire rental unit
  2. Marriotts Cove
Sailors’ Paradise - Stevens Cove Guest Quarters
SUPERHOST
  1. Entire rental unit
  2. Chester
Ye Olde Barne, Chester Village, NS
  1. Entire guest house
  2. Chester Basin
Rustic barn-inspired loft studio, sleeps 7
  1. Entire residential home
  2. Robinsons Corner
Country Home on Large Area Quiet and Peaceful
SUPERHOST
  1. Entire cottage
  2. Chester
Scotch Cove Retreat
SUPERHOST
  1. Entire cottage
  2. Chester
East Chester waterfront cottage on Scotch Cove
  1. Entire rental unit
  2. Chester
Central Chester Casa
SUPERHOST
  1. Entire residential home
  2. Chester
An Iconic Chester Home with Stunning Ocean Views

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