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

Chester Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chester holiday rentals

Outdoor spa tub

1. 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, (15 reviews)
"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$1,122
HK$1,464 total
includes taxes & fees
30 Sept - 1 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Exterior

2. 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, (22 reviews)
"Hot tub is Devine, everything is clean and thoughtfully provided. Basket of snacks was a sweet treat! We enjoyed the large deck and privacy very much ♥️we will definitely be back "
Canada
Suzanne
The price is HK$1,122
HK$1,464 total
includes taxes & fees
30 Sept - 1 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Desk, free WiFi

3. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (36 reviews)
"Check in and out was easy cute family that runs the place. Campground was very clean well-maintained fun areas for families for kids to play in the park fun pool washroom we're clean and maintained regularly. Definitely recommend for family fun."
Canada
David
The price is HK$667
HK$761 total
includes taxes & fees
22 Sept - 23 Sept
Oakhill Pines Campground
Premium bedding, pillow-top beds, free WiFi

4. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (76 reviews)
"The cabin was adorable, and the property was so clean. It was walking distance to everything in Mahone bay. Would definitely stay again!"
United States
Elizabeth
The price is HK$1,888
HK$2,344 total
includes taxes & fees
22 Sept - 23 Sept
Black Forest Cabins
Property grounds

5. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.4 out of 10, Exceptional, (25 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is HK$2,131
HK$3,500 total
includes taxes & fees
29 Sept - 30 Sept
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Exterior detail

6. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
9.8 out of 10, Exceptional, (17 reviews)
"Amenities are fantastic, very private"
Canada
francesco c.
The price is HK$1,122
HK$1,458 total
includes taxes & fees
8 Oct - 9 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
TV

7. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (115 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
The price is HK$1,122
HK$1,892 total
includes taxes & fees
1 Oct - 2 Oct
One bedroom fully equipped Mahone Bay luxury cottage
Interior

8. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (112 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is HK$1,122
HK$1,886 total
includes taxes & fees
9 Oct - 10 Oct
Mahone Bay Hide-Away
Interior

9. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (64 reviews)
"A beautifully curated hideaway. It is everything described and more: friendly hosts, minutes from shops and dining, yet, tucked away such that the only night sound is the chirping of frogs. We were quite delighted."
Canada
Karyn
The price is HK$1,262
HK$2,071 total
includes taxes & fees
21 Sept - 22 Sept
One bedroom fully equipped Mahone Bay luxury cottage
View from property

10. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Hubbards
8.6 out of 10, Excellent, (54 reviews)
"Sheets were stained and the house wasn’t up to my standards for cleanliness.It is cheap and a nice location and it was easy to communicate with the host."
Canada
Joanne
The price is HK$1,196
HK$1,562 total
includes taxes & fees
28 Sept - 29 Sept
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Marina

11. SUN, SAND, OCEAN, in Hubbards. What more do you need?

SUN, SAND, OCEAN, in Hubbards. What more do you need?
Hubbards
9.4 out of 10, Exceptional, (19 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is HK$1,655
HK$3,150 total
includes taxes & fees
20 Sept - 21 Sept
SUN, SAND, OCEAN, in Hubbards. What more do you need?
Property grounds

12. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Boutiliers Point
9.8 out of 10, Exceptional, (26 reviews)
"Everything was clean and cozy very quiet and friendly staff "
Canada
Adele S.
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Exterior detail

13. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is HK$1,010
HK$1,535 total
includes taxes & fees
5 Oct - 6 Oct
Red Barn Bed & Breakfast
Beach nearby, sun-loungers, beach towels

14. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (6 reviews)
"This property would be excellent for older couples and handicapped people. There's a ramp leading to the cottage and grab bars inside. Very peaceful and such a wonderful couple who owns it."
Canada
Betty
The price is HK$1,402
HK$2,193 total
includes taxes & fees
30 Sept - 1 Oct
Mermaid's Retreat - Caribou Lake Cottage!
Exterior

15. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.4 out of 10, Good, (6 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
The price is HK$1,406
HK$1,875 total
includes taxes & fees
4 Oct - 5 Oct
Orchard Cabin #4 - Hubbards Beach
Living area

16. Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay

Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
Mahone Bay
10.0 out of 10, Exceptional, (23 reviews)
"This was our second stay at this cottage and are planning to make this a yearly event. The cottage has everything you need, well appointed and very cozy! Location is also great."
Canada
Brauna R.
The price is HK$1,598
HK$2,999 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
Beach nearby

17. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.8 out of 10, Exceptional, (9 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
The price is HK$1,171
HK$1,891 total
includes taxes & fees
29 Sept - 30 Sept
Lake Mushamush Cottage!
Property grounds

18. 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, (14 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
The price is HK$1,453
HK$1,942 total
includes taxes & fees
12 Oct - 13 Oct
Pet-Friendly Glamping Dome close to Peggy’s Cove!
Marina

19. Ocean Sanctuary - The Salty Cribb Cabin

Ocean Sanctuary - The Salty Cribb Cabin
Rose Bay
9.2 out of 10, Wonderful, (5 reviews)
"When we arrived after a long trip we found the rooms were clean, welcoming and attractive. The cabin was well equipped and everything worked. Beautiful location, always enjoyed the drive up to Lunenberg."
United States
Paul K.
The price is HK$1,136
HK$2,447 total
includes taxes & fees
3 Oct - 4 Oct
Ocean Sanctuary - The Salty Cribb Cabin
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

Clifty Cove Motel

Clifty Cove Motel

10/10 Excellent
"Very nice friendly place and clean"
James 2-night trip
Posted 12 hours ago
Clifty Cove Motel

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?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside Chester is located by the ocean, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Chester?

Choose from 16 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Cultural attractions to visit include Chester Playhouse and Lordly House Museum. Chester Golf Club and Chester Art Center 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.