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, (17 reviews)
"Unique property. Cozy warm and welcoming from the get go. Owners would respond to questions within minutes. Accommodations were immaculate and had everything we needed. They've literally thought of everything. Can't wait to visit again"
Canada
Sandra
$179 nightly
The price is $204
Oct 26 - Oct 27
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.

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, (23 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
$147 nightly
The price is $168
Oct 26 - Oct 27
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A geodesic dome tent with a wooden frame and a transparent covering, situated in a forested area with trees and a cloudy sky in the background.

3. 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 reviews)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
$226 nightly
The price is $258
Oct 26 - Oct 27
Total with taxes and fees
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
A view of a waterfront property with a dock and a small building.

4. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Beautiful spot!"
United States
Kirby D.
$278 nightly
The price is $324
Oct 25 - Oct 26
Total with taxes and fees
Oceanfront Luxury Magical Views Sunset and Sunrise
A sunset view through a window with bare trees and a distant shoreline.

5. 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
8.8 out of 10, Excellent, (63 reviews)
"The owner was fantastic and he was really hospitable and very friendly. Highly Recommended and will come back again."
Canada
Chamok
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A small, two-story cabin with a deck, large windows, and a fireplace.

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.
$147 nightly
The price is $168
Oct 28 - Oct 29
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
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, (89 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
$165 nightly
The price is $189
Nov 3 - Nov 4
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, (7 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
$244 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
Mermaid's Retreat - Caribou Lake Cottage!
A wooden cabin bedroom with a bed, a hanging chair, and large windows offering a forest view.

9. Sunken Escapes ZEEK (Unit 6)

Sunken Escapes ZEEK (Unit 6)
Sunken Lake
9.4 out of 10, Exceptional, (3 reviews)
"Beautifully crafted cabins. We used the accessible cabin for the most part. It had everything we needed for a tranquil adventure. The host went above and beyond to accomodate our needs. Much thanks."
Canada
Toni M.
$137 nightly
The price is $156
Nov 4 - Nov 5
Total with taxes and fees
Sunken Escapes ZEEK (Unit 6)
A two-story house with a porch, a garage, and a driveway.

10. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"This property was comfortable and convenient and we enjoyed our stay here."
United States
Marty
$111 nightly
The price is $128
Oct 26 - Oct 27
Total with taxes and fees
Downtown Bridgewater Suite near River and Trails
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
9.6 out of 10, Exceptional, (27 reviews)
"Check in staff were very friendly and showed us around the cabin and facilities. Cabin was clean, had all required items for cooking and enjoying the stay."
United States
Kristopher H.
$165 nightly
The price is $193
Oct 25 - Oct 26
Total with taxes and fees
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A wooden building with a sign reading "The Knot."

12. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
$132 nightly
The price is $150
Oct 30 - Oct 31
Total with taxes and fees
Red Barn Bed & Breakfast
A lakeside view with trees, a dock, and a grassy area.

13. Lakeside Cottage Retreat-Your Year Round Getaway

Lakeside Cottage Retreat-Your Year Round Getaway
Windsor
9.6 out of 10, Exceptional, (5 reviews)
"The cottage is located on a beautiful lake. It was great for our short stay."
Canada
Kathryn
$252 nightly
The price is $288
Nov 8 - Nov 9
Total with taxes and fees
Lakeside Cottage Retreat-Your Year Round Getaway
A small white cabin with green trim and a porch, surrounded by greenery.

14. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.2 out of 10, Good, (7 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
$205 nightly
The price is $239
Oct 25 - Oct 26
Total with taxes and fees
Orchard Cabin #4 - Hubbards Beach
A wooden deck with two hammock swings overlooking a lake.

15. Bespoke Lake Cottage

Bespoke Lake Cottage
Kings County
9.2 out of 10, Wonderful, (12 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.
$201 nightly
The price is $229
Nov 15 - Nov 16
Total with taxes and fees
Bespoke Lake Cottage
A beach with clear water, a sandy shore, and a forested island in the distance.

16. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
Ingramport
9.8 out of 10, Exceptional, (124 reviews)
"Great location and beautiful spot. Our family of 5 really enjoyed our visit!!"
United States
Victoria W.
$311 nightly
The price is $363
Oct 24 - Oct 25
Total with taxes and fees
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A corner room with a TV, a clock, a sofa, a lamp, and a view of buildings through the window.

17. Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor
9.8 out of 10, Exceptional, (7 reviews)
"The place was very clean and well kept. Check in was super easy and Dan is very good with all the instructions and communication. Will come back for sure."
Canada
Lucie
$135 nightly
The price is $154
Nov 2 - Nov 3
Total with taxes and fees
Stylish Windsor Suite Near Wineries & Fundy Coast
A tented accommodation with a bed, two chairs, and a view of a lake.

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

Luxury lakefront dome with private beach, close to nature and town!
Lunenburg
10.0 out of 10, Exceptional, (43 reviews)
"This place exceeded expectations and was an absolute delight."
Canada
Sandie
$247 nightly
The price is $281
Oct 26 - Oct 27
Total with taxes and fees
Luxury lakefront dome with private beach, close to nature and town!
A wooden dock extending into a calm lake, surrounded by rocks and greenery.

19. CAIA Lakeside Retreat- Sunken Lake, NS

CAIA Lakeside Retreat- Sunken Lake, NS
Sunken Lake
9.4 out of 10, Exceptional, (17 reviews)
"Pet friendly"
Canada
Lori
$215 nightly
The price is $245
Nov 8 - Nov 9
Total with taxes and fees
CAIA Lakeside Retreat- Sunken Lake, NS
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

Old Orchard Inn

Old Orchard Inn

10/10 Excellent
"Rooms are spacious and easy to access. While a bit dated, they are comfortable and clean. On-site restaurant/bar is top notch. Excellent local selections and a beautiful view! Less than 10 minutes to several wineries, and directly off the highway, this is a perfect spot to start your exploration of the region."
Kari 1-night trip
Posted 6 hours ago
Old Orchard Inn

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 $149 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.