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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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, (16 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 ￥22,119
￥28,872 total
includes taxes & fees
Oct 18 - Oct 19
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
The price is ￥22,119
￥28,872 total
includes taxes & fees
Oct 18 - Oct 19
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small, two-story cabin with a deck, large windows, and a fireplace.

3. 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 ￥22,119
￥28,872 total
includes taxes & fees
Oct 8 - Oct 9
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, (58 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 ￥20,106
￥26,451 total
includes taxes & fees
Oct 15 - Oct 16
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. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (27 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is ￥43,132
￥70,683 total
includes taxes & fees
Oct 5 - Oct 6
Oceanfront Luxury Magical Views Sunset and Sunrise
A bright living room with a white sofa, a coffee table, and a potted plant.

6. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (117 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
The price is ￥22,119
￥37,193 total
includes taxes & fees
Oct 17 - Oct 18
One bedroom fully equipped Mahone Bay luxury cottage
A dock with boats, a clear blue lake, and a forested island.

7. 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 ￥27,648
￥43,244 total
includes taxes & fees
Oct 13 - Oct 14
Mermaid's Retreat - Caribou Lake Cottage!
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.

8. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (83 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
The price is ￥36,854
￥45,796 total
includes taxes & fees
Nov 1 - Nov 2
Black Forest Cabins
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

9. 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 ￥22,119
￥37,193 total
includes taxes & fees
Oct 9 - Oct 10
Mahone Bay Hide-Away
A calm lake with boats docked at the pier, surrounded by trees.

10. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.4 out of 10, Exceptional, (11 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
The price is ￥23,092
￥37,293 total
includes taxes & fees
Oct 4 - Oct 5
Lake Mushamush Cottage!
A wooden cabin bedroom with a bed, a hanging chair, and large windows offering a forest view.

11. 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.
The price is ￥14,632
￥29,828 total
includes taxes & fees
Oct 25 - Oct 26
Sunken Escapes ZEEK (Unit 6)
A wooden deck with two hammock swings overlooking a lake.

12. 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.
The price is ￥11,612
￥35,551 total
includes taxes & fees
Nov 1 - Nov 2
Bespoke Lake Cottage
A sandy beach with people walking along the shore.

13. 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
The price is ￥7,697
￥19,848 total
includes taxes & fees
Oct 7 - Oct 8
Downtown Bridgewater Suite near River and Trails
A sauna with a view of the sea, wooden walls, and a stone heater.

14. 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.
The price is ￥25,547
￥34,158 total
includes taxes & fees
Oct 4 - Oct 5
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A two-story building with a balcony and multiple windows.

15. Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and very well put together, very new and modern would definitely stay there again"
Canada
Ryan
The price is ￥11,502
￥19,164 total
includes taxes & fees
Oct 2 - Oct 3
Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

16. 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
The price is ￥20,902
￥23,828 total
includes taxes & fees
Oct 18 - Oct 19
Micro Boutique Living Wolfville
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
9.6 out of 10, Exceptional, (4 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
The price is ￥13,935
￥23,829 total
includes taxes & fees
Oct 5 - Oct 6
Stylish Windsor Suite Near Wineries & Fundy Coast
A small white cabin with green trim and a porch, surrounded by greenery.

18. 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 ￥27,726
￥36,978 total
includes taxes & fees
Oct 4 - Oct 5
Orchard Cabin #4 - Hubbards Beach
A wooden deck with lounge chairs, a wooden bench, and a house with large windows overlooking a body of water.

19. New Waterfront Cottag on Hirtle Lake

New Waterfront Cottag on Hirtle Lake
East Clifford
9.0 out of 10, Wonderful, (6 reviews)
"It was very clean and I really enjoyed my stay!"
Canada
Tibor
The price is ￥16,191
￥51,112 total
includes taxes & fees
Oct 5 - Oct 6
New Waterfront Cottag on Hirtle Lake
A lakeside view with trees, a dock, and a grassy area.

20. Lakeside Cottage Retreat-Your Year Round Getaway

Lakeside Cottage Retreat-Your Year Round Getaway
Windsor
9.4 out of 10, Exceptional, (3 reviews)
"The cottage is located on a beautiful lake. It was great for our short stay."
Canada
Kathryn
The price is ￥34,339
￥44,694 total
includes taxes & fees
Oct 4 - Oct 5
Lakeside Cottage Retreat-Your Year Round Getaway
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

Slumber Inn

Slumber Inn

8/10 Good
"Nice place to stay but the carpet wasn’t great for allergies! Rooms are nice and in a good location for seeing the Valley!"
Sean 3-night trip
Posted 1 hour ago
Slumber Inn

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Vacation Apartments in Chester

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