A large, two-story house with a steeply pitched roof and a chimney.

Holiday Homes in Chester

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chester holiday homes

A modern living room with a flat-screen TV, a fireplace, a sofa set, and a large window with blinds.

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
Chester
Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
A view of a waterfront property with a dock and a small building.

2. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Excellent location with beautiful marina and ocean view from the property. Very well maintained with excellent host Holly."
United States
Cynthia K G.
The price is NZ$429
includes taxes & fees
29 Nov - 30 Nov
Oceanfront Luxury Magical Views Sunset and Sunrise
A wooden cabin and a geodesic dome structure with seating and a fire pit, surrounded by a forest.

3. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Pet-Friendly Glamping Dome close to Peggy’s Cove!
Seabright
10.0 out of 10, Exceptional, (22 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
The price is NZ$439
includes taxes & fees
14 Nov - 15 Nov
Pet-Friendly Glamping Dome close to Peggy’s Cove!
A cozy living room with a grey sofa, a white coffee table, and a wooden ceiling.

4. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax
Boutiliers Point
9.2 out of 10, Wonderful, (15 reviews)
"Great cottage and location is amazing! "
Canada
Joanna
The price is NZ$364
includes taxes & fees
15 Nov - 16 Nov
Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax
A bedroom with a bed, bedside tables, a chair, a desk, a dresser, and a ceiling fan.

5. Pretty Bachelor with Balcony near River & Trails

Pretty Bachelor with Balcony near River & Trails
Bridgewater
2.0 out of 10, (1 review)
The price is NZ$239
includes taxes & fees
12 Nov - 13 Nov
Pretty Bachelor with Balcony near River & Trails
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

8/10 Good
"room clean and breakfast good"
Daniel 1-night trip
Posted 20 hours ago
Days Inn & Conference Center by Wyndham Bridgewater

Find out more about Chester

Chester Holiday Homes information

Number of reviews
66
Accommodation
71 Holiday Homes
Lowest Price
NZ$239
Highest Price
NZ$439