A calm lake with boats, a stone dock, and houses with a stone wall and trees in the background.

Vacation Rentals in Chester

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Top Cities in Chester

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

Chester

Chester

Our top choices for Chester vacation rentals

A wooden deck with a hot tub surrounded by trees.

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)
$162 nightly
The price is $185
Sep 30 - Oct 1
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small, two-story cabin with a deck, large windows, and a fireplace.

2. 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.
$162 nightly
The price is $184
Oct 8 - Oct 9
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small cabin with a deck, a door, and a window.

3. 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
$162 nightly
The price is $185
Sep 28 - Sep 29
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A sunset view through a window with bare trees and a distant shoreline.

4. 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
$169 nightly
The price is $193
Oct 5 - Oct 6
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A view of a waterfront property with a dock and a small building.

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

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.2 out of 10, Wonderful, (27 reviews)
"Beautiful spot!"
United States
Kirby D.
$381 nightly
The price is $444
Sep 29 - Sep 30
Total with taxes and fees
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
A wooden door with a view of an outdoor deck and a chair.

6. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (37 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
$81 nightly
The price is $93
Sep 28 - Sep 29
Total with taxes and fees
Oakhill Pines Campground
A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

7. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (78 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
$260 nightly
The price is $296
Sep 29 - Sep 30
Total with taxes and fees
Black Forest Cabins
A dock with boats, a clear blue lake, and a forested island.

8. 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
$242 nightly
The price is $276
Sep 26 - Sep 27
Total with taxes and fees
Mermaid's Retreat - Caribou Lake Cottage!
An outdoor patio with a grill, two chairs, and a table.

9. Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (1 review)
"First, the host is FANTASTIC! This was my first non-hotel experience and she made it a great one! Extremely helpful! The unit was super clean and very nice for its size! Exactlyas show!, No smells at all! I would highly recommend your stay here! I will be booking a different unit next time just to experience more of these beautiful units!"
Canada
Lori
$123 nightly
The price is $141
Oct 7 - Oct 8
Total with taxes and fees
Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley
A wooden deck with two hammock swings overlooking a lake.

10. Bespoke Lake Cottage

Bespoke Lake Cottage
Kings County
9.4 out of 10, Exceptional, (10 reviews)
"We have a lovely stay - our only complaint is that we didn't book for long enough! The cottage is very charming and very clean. Bed is comfortable and kitchen had all equipment needed for food prep. "
Canada
Lily S.
$228 nightly
The price is $259
Oct 15 - Oct 16
Total with taxes and fees
Bespoke Lake Cottage
A sauna with a view of the sea, wooden walls, and a stone heater.

11. 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.
$187 nightly
The price is $219
Sep 30 - Oct 1
Total with taxes and fees
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A wooden deck with lounge chairs, a wooden bench, and a house with large windows overlooking a body of water.

12. New Waterfront Cottag on Hirtle Lake

New Waterfront Cottag on Hirtle Lake
East Clifford
8.8 out of 10, Excellent, (5 reviews)
"It was very clean and I really enjoyed my stay!"
Canada
Tibor
$297 nightly
The price is $338
Oct 21 - Oct 22
Total with taxes and fees
New Waterfront Cottag on Hirtle Lake
A calm lake with boats docked at the pier, surrounded by trees.

13. 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
$210 nightly
The price is $239
Sep 27 - Sep 28
Total with taxes and fees
Lake Mushamush Cottage!
A cabin with a wooden exterior, a balcony, and a grill area.

14. Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)
Sunken Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very peaceful and relaxed. Close to amenities"
Canada
Murray
$195 nightly
The price is $221
Oct 13 - Oct 14
Total with taxes and fees
Sunken Escapes Kenny's (Unit 5)
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

15. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,330 reviews)
"Location is perfect"
Canada
Kelly
$134 nightly
The price is $153
Oct 18 - Oct 19
Total with taxes and fees
Micro Boutique Living Wolfville
A hallway with a wooden door frame, a gray patterned rug, and a white door leading to a room with blue walls.

16. Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit

Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit
Upper Hammonds Plains
9.6 out of 10, Exceptional, (27 reviews)
"Beautiful place to stay, the art work is amazing! "
Canada
Brooklyn
$243 nightly
The price is $285
Sep 30 - Oct 1
Total with taxes and fees
Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit
A residential area with a house, a swimming pool, and a marina with boats.

17. 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.
$341 nightly
The price is $399
Sep 27 - Sep 28
Total with taxes and fees
SUN, SAND, OCEAN, in Hubbards. What more do you need?
A sandy beach with people walking along the shore.

18. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.0 out of 10, Wonderful, (2 reviews)
"Excellent kitchenette having everything needed to cook for yourself -ceiling fans needed a serious cleaning but not a dealbreaker"
Canada
Tim
$119 nightly
The price is $137
Sep 30 - Oct 1
Total with taxes and fees
Downtown Bridgewater Suite near River and Trails
A small white cabin with green trim and a porch, surrounded by greenery.

19. 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.
$203 nightly
The price is $237
Sep 30 - Oct 1
Total with taxes and fees
Orchard Cabin #4 - Hubbards Beach
A bright living room with a white sofa, a coffee table, and a potted plant.

20. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
$209 nightly
The price is $239
Oct 17 - Oct 18
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage
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

Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

8/10 Good
"We were planning to stay for two days, but the bed was so hard. It was like sleeping on concrete since it was so busy in town. We had to go to a different town and look for a hotel with a better bed with the help of the local visitor information center we found a good place and thankfully the owners of the Atlantic view hotel gave us a refund for the second night. They didn’t have to, but they did and we appreciated that. the room itself is pleasant enough, but the chairs are hard. The little sofa is hard. Nothing was comfortable to sit on and it’s very outdated. I wouldn’t call it quaint. It’s just outdated. It’s in a pleasant very centrally, located part of town close to everything we need so anything was a very short drive. We did appreciate that. We drove in town of Hubbard’s, which was about a 30 minute drive for our second hotel so we couldn’t spend the night in the original town that we wanted to."
John 2-night trip
Posted less than an hour ago
Atlantic View Motel and Cottages

Find out more about Chester

Discover your perfect Chester vacation rental with Expedia

How many vacation rentals are available in Chester?


Expedia has plenty of vacation rentals to choose from in and around  Chester, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Chester?


The selection of Chester vacation rentals we have selected for you start as low as $93 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Chester?


Vacation rentals in Chester come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Chester vacation rentals to suit everyone. 


Why should I choose a vacation rental in Chester?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Chester?


Find vacation rentals in Chester by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Chester.  


What amenities are available in a vacation rental in Chester?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Chester vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Chester?   


Everytime is a great time to head to Chester! Staying in a Chester vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Chester. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Chester vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Chester, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Chester vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.