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

Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chester vacation 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, (12 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 ￥22,321
￥29,136 total
includes taxes & fees
Sep 21 - Sep 22
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, (21 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 ￥22,321
￥29,008 total
includes taxes & fees
Oct 9 - Oct 10
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Premium bedding, pillowtop beds, WiFi (free)

3. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (75 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 ￥33,032
￥41,518 total
includes taxes & fees
Sep 9 - Sep 10
Black Forest Cabins
Cabin, 1 Double Bed, Shared Bathroom | Desk, WiFi (free)

4. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (33 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 ￥13,015
￥14,837 total
includes taxes & fees
Sep 13 - Sep 14
Oakhill Pines Campground
Exterior detail

5. 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 ￥22,321
￥29,136 total
includes taxes & fees
Sep 21 - Sep 22
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Interior

6. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (110 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is ￥25,409
￥41,325 total
includes taxes & fees
Sep 17 - Sep 18
Mahone Bay Hide-Away
Property grounds

7. 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 ￥42,348
￥70,064 total
includes taxes & fees
Sep 10 - Sep 11
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
View from property

8. 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, (53 reviews)
"It was a nice stay"
United States
Deanna P.
The price is ￥26,116
￥34,098 total
includes taxes & fees
Sep 21 - Sep 22
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
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 ￥25,409
￥41,454 total
includes taxes & fees
Sep 18 - Sep 19
One bedroom fully equipped Mahone Bay luxury cottage
Beach nearby

10. 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 ￥23,580
￥38,081 total
includes taxes & fees
Sep 9 - Sep 10
Lake Mushamush Cottage!
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, (18 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is ￥33,314
￥63,416 total
includes taxes & fees
Sep 13 - Sep 14
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, (25 reviews)
"Everything was clean and cozy very quiet and friendly staff "
Canada
Adele S.
The price is ￥21,702
￥29,088 total
includes taxes & fees
Sep 20 - Sep 21
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, (11 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is ￥20,327
￥30,897 total
includes taxes & fees
Oct 5 - Oct 6
Red Barn Bed & Breakfast
Exterior

14. 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 ￥27,272
￥36,415 total
includes taxes & fees
Sep 13 - Sep 14
Orchard Cabin #4 - Hubbards Beach
Fridge, stovetop, cookware/dishes/utensils, spices

15. Lunenburg Floating Cottages

Lunenburg Floating Cottages
Lunenburg
The price is ￥26,934
￥35,082 total
includes taxes & fees
Sep 21 - Sep 22
Lunenburg Floating Cottages
Marina

16. Ocean Sanctuary - The Salty Cribb Cabin

Ocean Sanctuary - The Salty Cribb Cabin
Rose Bay
10.0 out of 10, Exceptional, (4 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 ￥25,409
￥53,029 total
includes taxes & fees
Oct 3 - Oct 4
Ocean Sanctuary - The Salty Cribb Cabin
Living area

17. 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, (22 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 ￥32,185
￥60,379 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
Terrace/patio

18. SUN, SAND, OCEAN in Hubbards Nova Scotia

SUN, SAND, OCEAN in Hubbards Nova Scotia
Hubbards
9.6 out of 10, Exceptional, (11 reviews)
"Cottage location was ideal for seeing sites in the area. We loved sitting on the dock, watching sunsets and relaxing. We would definitely recommend this rental."
Canada
Gloria L.
The price is ￥36,702
￥67,910 total
includes taxes & fees
Sep 9 - Sep 10
SUN, SAND, OCEAN in Hubbards Nova Scotia
Interior

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

Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)
Lunenburg
9.2 out of 10, Wonderful, (5 reviews)
"Great stay!!"
Canada
heather p.
The price is ￥26,832
￥44,492 total
includes taxes & fees
Oct 7 - Oct 8
Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)
Living area

20. 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
8.4 out of 10, Very Good, (10 reviews)
"Great location for us and very clean and spacious."
Canada
Christina
The price is ￥21,457
￥37,657 total
includes taxes & fees
Sep 12 - Sep 13
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

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?

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

How many vacation rentals will I find in Chester?

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

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 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.