Chester Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Chester holiday rentals

Meeting facility
Black Forest Cabins

Black Forest Cabins

3.0 star property
Mahone Bay
10.0 out of 10, Exceptional, (19)
"Bed was very comfortable,and clean and spacious. Everything I needed was there and close to trails and the downtown."
Canada
Mary
The price is HK$1,123
HK$1,473 total
includes taxes & fees
14 Dec - 15 Dec
Black Forest Cabins
Room
Private Balcony View Riverside Walk Prime Downtown

Private Balcony View Riverside Walk Prime Downtown

2.0 star property
Bridgewater
The price is HK$393
HK$864 total
includes taxes & fees
11 Dec - 12 Dec
Private Balcony View Riverside Walk Prime Downtown
Sun-loungers, beach towels
Wilson's Coastal Club - C2

Wilson's Coastal Club - C2

Boutiliers Point
9.8 out of 10, Exceptional, (8)
"Wonderful, friendly hosts, a beautiful, peaceful location. We had a great time!"
Canada
Stephanie Y.
The price is HK$940
HK$1,283 total
includes taxes & fees
16 Dec - 17 Dec
Wilson's Coastal Club - C2
Desk, free WiFi
Oakhill Pines Campground

Oakhill Pines Campground

3.0 star property
Oak Hill
9.0 out of 10, Wonderful, (16)
"Great place"
Canada
Thelma
The price is HK$629
HK$717 total
includes taxes & fees
11 Dec - 12 Dec
Oakhill Pines Campground
Living area
Hot Choco Bar Backyard Access Private Entry

Hot Choco Bar Backyard Access Private Entry

2.0 star property
Bridgewater
The price is HK$573
HK$978 total
includes taxes & fees
16 Dec - 17 Dec
Hot Choco Bar Backyard Access Private Entry
Outdoor spa tub
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Windsor Road
10.0 out of 10, Exceptional, (7)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Canada
Carol
The price is HK$1,011
HK$1,332 total
includes taxes & fees
11 Dec - 12 Dec
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Exterior detail
Red Roof Bed & Breakfast

Red Roof Bed & Breakfast

Lunenburg
9.6 out of 10, Exceptional, (9)
"A lovely little cottage, with the added bonus of a gift shop filled with curious trinkets! Would definitely stay here again if I’m ever back in Lunenberg."
Canada
Raeleen
The price is HK$1,006
HK$1,531 total
includes taxes & fees
11 Dec - 12 Dec
Red Roof Bed & Breakfast
Marina
Sailboat Suite - Heart of Lunenburg

Sailboat Suite - Heart of Lunenburg

Lunenburg
8.8 out of 10, Excellent, (3)
"Good and quiet location. Not properly cleaned (pictures attached)."
Canada
Anonymous traveller
The price is HK$667
HK$1,420 total
includes taxes & fees
11 Dec - 12 Dec
Sailboat Suite - Heart of Lunenburg
Sauna
Wilson's Coastal Club - C1

Wilson's Coastal Club - C1

Boutiliers Point
9.6 out of 10, Exceptional, (9)
"Great cottage and location is amazing! "
Canada
Joanna
The price is HK$1,372
HK$1,836 total
includes taxes & fees
14 Dec - 15 Dec
Wilson's Coastal Club - C1
Exterior
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Lunenburg
9.0 out of 10, Wonderful, (7)
"Close to town , clean and comfortable "
United States
Tom D.
The price is HK$710
HK$1,405 total
includes taxes & fees
11 Dec - 12 Dec
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Private kitchen
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Bridgewater
9.4 out of 10, Exceptional, (3)
"As described and in a great location!"
United States
Erin E.
The price is HK$1,011
HK$1,952 total
includes taxes & fees
11 Dec - 12 Dec
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Interior
Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites

Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites

Chester Basin
9.8 out of 10, Exceptional, (14)
"There’s so much about Dordéan Suites to like: a contemporary, fun alternative to large, impersonal corporate roadside hotel. Loved our place, loved our stay! "
United States
Karil
The price is HK$1,011
HK$1,332 total
includes taxes & fees
15 Dec - 16 Dec
Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites
Private kitchen
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,

ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,

Bridgewater
8.4 out of 10, Very good, (6)
"Great location. Surprisingly quiet given its proximity to a Main Street. "
United States
Jacqueline S.
The price is HK$708
HK$1,208 total
includes taxes & fees
18 Dec - 19 Dec
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
Property grounds
The Lookout Dome One - Private Hot Tub

The Lookout Dome One - Private Hot Tub

LaHave
10.0 out of 10, Exceptional, (20)
"Beautiful stay. "
Canada
Kyle M.
The price is HK$1,770
HK$2,909 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Lookout Dome One - Private Hot Tub
Terrace/patio
Luxury lakefront dome with private beach, close to nature and town!

Luxury lakefront dome with private beach, close to nature and town!

Lunenburg
9.8 out of 10, Exceptional, (10)
"Great location just outside of Lunenburg, quiet and remote. Beautiful inside!"
United States
Kevin C.
The price is HK$1,545
HK$2,344 total
includes taxes & fees
11 Dec - 12 Dec
Luxury lakefront dome with private beach, close to nature and town!
Marina
Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore
9.6 out of 10, Exceptional, (20)
"We took day trips from Holly’s home all week, but the view off the balcony was a delight to return to. "
United States
frances p.
The price is HK$1,264
HK$2,136 total
includes taxes & fees
11 Dec - 12 Dec
Oceanfront Luxury Magical Views Sunset and Sunrise
Interior
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Bridgewater
8.8 out of 10, Excellent, (3)
"Everything was clean. We'll set up Would stay again for sure"
Canada
Porter F.
The price is HK$1,011
HK$2,031 total
includes taxes & fees
13 Dec - 14 Dec
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Living area
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Chester
9.0 out of 10, Wonderful, (2)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
The price is HK$1,567
HK$2,043 total
includes taxes & fees
16 Dec - 17 Dec
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
1 bedroom, desk, free WiFi, bed sheets
The Lookout Dome Two - Private Hot Tub

The Lookout Dome Two - Private Hot Tub

LaHave
9.8 out of 10, Exceptional, (10)
"Unique property with a great view of the ocean. Great location for exploring the surrounding towns and coastline."
Canada
Gary D.
The price is HK$1,770
HK$2,909 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Lookout Dome Two - Private Hot Tub
Sauna
Wilson's Coastal Club - C6

Wilson's Coastal Club - C6

Boutiliers Point
10.0 out of 10, Exceptional, (9)
"Beautiful location! Great view of the bay.. "
Canada
Joan
The price is HK$839
HK$1,165 total
includes taxes & fees
11 Dec - 12 Dec
Wilson's Coastal Club - C6
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

The Dockside Inn & Restaurant

The Dockside Inn & Restaurant

10/10 Excellent
"Room was clean and cozy, lots of amenities. Good bathtub, had a decent sized mini fridge and a microwave and coffee machine. Had a very beautiful view. Food from the restaurant was tasty and brought right to your room. Would rent again"
Darian 1-night trip
Posted 8 hours ago
The Dockside Inn & Restaurant

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its golf courses and theatres. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best holiday rentals that Chester has to offer?

Mahone Bay Hide-Away : This holiday home rental outside of Chester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Chester?

Choose from 14 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Cultural attractions to visit include Lordly House Museum and Chester Playhouse. Tancook Island and Chester Golf Club are other places to visit while you're in town.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.