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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.

Tower in Broad Cove
Shackup Tower - 30 ft in the air & hot tub
Perched high on an ocean hillside, built on 30 ft tall steel legs, the cozy quarters above are akin to an old ship’s cabin. With 360 views at 30ft up you can chart the sun and stars across the sky, set your rhythm to the ebb & flow of the tide and scout the surf from above. Greet the evenings with a cozy woodstove, sunset with drinks on the deck, moonrise with a dip in the hottub & mornings with fresh espresso. Permit yourself to depart land for a while and come stand watch at The Tower.
$515 SGD per night
Loft in Lunenburg
‘The BOHO retreat’ (entire ‘loft’ suite)
A newly constructed loft apartment, nestled between Lunenburg and Mahone bay. Minutes from either. A beautiful open plan living space, high end bathroom, all rustically finished with reclaimed 200 yr old Douglas fir. A stunning private deck, to enjoy the beginning or end of your adventure around the south shore! Easy self check in, parking, and private. Please note- there is a kitchenette/coffee bar-no stove/oven to cook on. (Please see ‘amenities’ list, for full description).
$114 SGD per night
Cottage in Chester
Moss Cottage on the Lake
Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.
$167 SGD per night

Stay near Chester's top sights

SENSEA Nordic Spa39 locals recommend
The Kiwi Cafe44 locals recommend
The Rope Loft36 locals recommend
Fo'c'sle Tavern29 locals recommend
The Stretch Diner5 locals recommend
Oceanview Home and Garden3 locals recommend

Other great holiday rentals in Chester

Chalet in Lunenburg
Waterfront Honeymoon Honeymoon Loft
$211 SGD per night
Townhouse in Chester Basin
Tranquility's Equilibrium Too - Oceanside retreat
$96 SGD per night
Tiny home in Lunenburg
Tiny house living in Lunenburg Town
$114 SGD per night
Tiny home in Nova Scotia
Cozy Cottage on South Shore. 30 min from Halifax!
$65 SGD per night
Chalet in Petite Rivière Bridge
Stunning, secluded chalet with wood fired hot tub
$271 SGD per night
Cottage in Mahone Bay
Getaway by the Bay
$127 SGD per night
Guest suite in Hubbards
Lakefront Eco Oasis, Cove Cottage Studio Suite
$120 SGD per night
Guest house in Chester
The Little Caboose
$183 SGD per night
Home in Chester
Charming three bedroom century home In Chester
$132 SGD per night
Home in Mahone Bay
Mahone Bay Ocean Retreat
$351 SGD per night
Home in Chester
Relaxed Chester home walking distance to town
$123 SGD per night
Flat in Marriotts Cove
Sailors’ Paradise - Stevens Cove Guest Quarters
$153 SGD per night

Quick stats about holiday rentals in Chester

Total rentals

50 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

820 reviews

Nightly prices starting at

$80 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. Canada
  3. Nova Scotia
  4. Chester