Chester Vacation Rentals

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Check prices for these dates

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Chester vacation rentals

Cabin, 1 Double Bed, Shared Bathroom | Desk, free WiFi
Oakhill Pines Campground

Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
9.0 out of 10, Wonderful, (16)
"Staff was super welcoming and cabin was all set for us! "
Canada
Andrea
The price is ￥12,664
￥14,437 total
includes taxes & fees
Jan 9 - Jan 10
Oakhill Pines Campground
Property grounds
Wilson's Coastal Club - C6

Wilson's Coastal Club - C6

Wilson's Coastal Club - C6
Boutiliers Point
10.0 out of 10, Exceptional, (9)
"The cabin was very private and it was nice having the hot tub on our front deck."
Canada
Jane T.
The price is ￥14,587
￥20,737 total
includes taxes & fees
Jan 11 - Jan 12
Wilson's Coastal Club - C6
Premium bedding, pillowtop beds, free WiFi
Black Forest Cabins

Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
10.0 out of 10, Exceptional, (22)
"Great spot for a special night out … beds were super comfortable "
Canada
Caroline
The price is ￥23,067
￥30,163 total
includes taxes & fees
Feb 1 - Feb 2
Black Forest Cabins
Outdoor spa tub
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
10.0 out of 10, Exceptional, (17)
"Room was spotless so clean and cute with snacks and a cute card !! It was so perfect for a little get away. We stayed there after spending the day at the Sensea Nortic Spa, it was great to come back to more relaxation with the hot tub and adorable room! "
Canada
Isabel
The price is ￥16,848
￥22,816 total
includes taxes & fees
Jan 11 - Jan 12
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Exterior detail
Red Roof Bed & Breakfast

Red Roof Bed & Breakfast

Red Roof Bed & Breakfast
Lunenburg
9.6 out of 10, Exceptional, (9)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is ￥20,241
￥30,809 total
includes taxes & fees
Jan 9 - Jan 10
Red Roof Bed & Breakfast
Outdoor spa tub
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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 ￥16,848
￥22,816 total
includes taxes & fees
Jan 11 - Jan 12
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Marina
Sailboat Suite - Heart of Lunenburg

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 traveler
The price is ￥13,433
￥28,591 total
includes taxes & fees
Jan 30 - Jan 31
Sailboat Suite - Heart of Lunenburg
Exterior detail
Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)

Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)

Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)
Lunenburg
9.0 out of 10, Wonderful, (4)
"Great stay!!"
Canada
heather p.
The price is ￥12,640
￥26,398 total
includes taxes & fees
Jan 9 - Jan 10
Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)
TV
Hot Choco Bar Backyard Access Private Entry

Hot Choco Bar Backyard Access Private Entry

Hot Choco Bar Backyard Access Private Entry
2.0 star property
Bridgewater
10.0 out of 10, Exceptional, (1)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
The price is ￥12,438
￥20,740 total
includes taxes & fees
Jan 21 - Jan 22
Hot Choco Bar Backyard Access Private Entry
Iron/ironing board, WiFi, bed sheets
Private Balcony View Riverside Walk Prime Downtown

Private Balcony View Riverside Walk Prime Downtown

Private Balcony View Riverside Walk Prime Downtown
2.0 star property
Bridgewater
The price is ￥10,656
￥20,609 total
includes taxes & fees
Jan 13 - Jan 14
Private Balcony View Riverside Walk Prime Downtown
Property grounds
Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.6 out of 10, Exceptional, (20)
"Excellent unit and very clean.The view was awesome.Highly recommended for a wonderful place to stay."
Canada
John S.
The price is ￥19,788
￥35,473 total
includes taxes & fees
Jan 14 - Jan 15
Oceanfront Luxury Magical Views Sunset and Sunrise
1 bedroom, iron/ironing board, WiFi, bed sheets
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,

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 ￥14,248
￥24,323 total
includes taxes & fees
Jan 9 - Jan 10
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
Property grounds
Wilson's Coastal Club - C3

Wilson's Coastal Club - C3

Wilson's Coastal Club - C3
Boutiliers Point
10.0 out of 10, Exceptional, (12)
"Very nice cottage, steps from the beach"
United States
Christine
The price is ￥13,456
￥19,409 total
includes taxes & fees
Jan 11 - Jan 12
Wilson's Coastal Club - C3
Interior
The Lookout Dome Two - Private Hot Tub

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 ￥35,619
￥58,432 total
includes taxes & fees
Jan 9 - Jan 10
The Lookout Dome Two - Private Hot Tub
Living area
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.

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 ￥20,354
￥40,876 total
includes taxes & fees
Jan 9 - Jan 10
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Property grounds
Wilson's Coastal Club - C7

Wilson's Coastal Club - C7

Wilson's Coastal Club - C7
Boutiliers Point
9.6 out of 10, Exceptional, (10)
"Accommodation was excellent, particularly the hot tub overlooking the bay. "
Canada
David B.
The price is ￥20,241
￥27,376 total
includes taxes & fees
Jan 11 - Jan 12
Wilson's Coastal Club - C7
Spa
Wilson's Coastal Club - C4

Wilson's Coastal Club - C4

Wilson's Coastal Club - C4
Boutiliers Point
10.0 out of 10, Exceptional, (7)
"It was lovely really enjoyed the property.. loved hot tub and sauna!!"
Canada
Mark R.
The price is ￥20,241
￥27,376 total
includes taxes & fees
Jan 12 - Jan 13
Wilson's Coastal Club - C4
Property grounds
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

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 ￥31,548
￥41,121 total
includes taxes & fees
Jan 11 - Jan 12
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
1 bedroom, WiFi
Luxury lakefront dome with private beach, close to nature and town!

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)
"Perfect spot for a peaceful getaway with a great view. "
Canada
Alan L.
The price is ￥31,096
￥47,180 total
includes taxes & fees
Jan 9 - Jan 10
Luxury lakefront dome with private beach, close to nature and town!
Terrace/patio
The Lookout Dome One - Private Hot Tub

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 ￥35,619
￥58,561 total
includes taxes & fees
Jan 11 - Jan 12
The Lookout Dome One - Private Hot Tub
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
"The owner and staff were unbelievably personable. Mike, the owner was truly a gem. The dockside was an amazing place to stay with great water views and amazing proximity to downtown shopping. The room is extremely clean and spacious and it was such a delight. We loved eating at the restaurant as well. That was certainly a plus. Breakfast with The view and the sunrise and sunsets were incredible. Can't wait to go back again."
Maria 2-night trip
Posted 6 days 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 vacation rentals in Chester?

Yes, there are vacation rentals close to the most popular sights in Chester, or you can choose a secluded option if you'd like a relaxing place to stay. Chester is known for its golf courses and theaters. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best vacation rentals in Chester?

Spacious Exclusive 5-bedroom house in fabulous Chester with WiFi, AC: Visitors give good reviews to this Chester vacation home rental, which offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals will I find in Chester?

Choose from 13 Expedia vacation rentals in Chester for a memorable vacation.

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 vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.