Search Residences in Chester from CA $104

  • 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

Find vacation rentals that suit your style

Cottage image
Cottages
Cottages
cabin image
Cabins
Cabins

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A modern living room with a flat-screen TV, a fireplace, a sofa set, and a large window with blinds.

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
Chester
Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
A hotel with a large outdoor patio area, multiple balconies, and a well-lit entrance.

2. Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre
3.5 star property
Western Shore
8.4 out of 10, Very good, (638 reviews)
"Great place"
Canada
Angela
The price is CA $150
CA $171 total
includes taxes & fees
Nov 11 - Nov 12
Oak Island Resort & Conference Centre
A two-story house with a gabled roof and a front porch.

3. Fairmont House Bed & Breakfast

Fairmont House Bed & Breakfast
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (334 reviews)
"Wonderful place to stay, great location, amazing breakfast, personable staff."
Canada
Marci
The price is CA $200
CA $228 total
includes taxes & fees
Nov 8 - Nov 9
Fairmont House Bed & Breakfast
A pathway leading to a house surrounded by lush greenery and a well-maintained garden.

4. Miller House By the Bay

Miller House By the Bay
2.0 star property
mahone bay
9.8 out of 10, Exceptional, (263 reviews)
"Great place to visit"
Canada
David
The price is CA $170
CA $194 total
includes taxes & fees
Nov 8 - Nov 9
Miller House By the Bay
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.

5. 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
The price is CA $224
CA $290 total
includes taxes & fees
Nov 8 - Nov 9
Black Forest Cabins
A table with two wine glasses and a vase of flowers by a window overlooking a harbor.

6. Rum Runner Inn

Rum Runner Inn
4.0 star property
Lunenburg Waterfront
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice location, very comfortable bed."
United States
Kathleen
The price is CA $229
CA $261 total
includes taxes & fees
Nov 7 - Nov 8
Rum Runner Inn
A hotel room with two beds, a large window, and artwork on the walls.

7. The Homeport Motel

The Homeport Motel
2.0 star property
Lunenburg
9.2 out of 10, Wonderful, (857 reviews)
"It was a great stay"
Canada
Julie
The price is CA $105
CA $120 total
includes taxes & fees
Nov 9 - Nov 10
The Homeport Motel
A cozy living room with a grey sofa, a wooden staircase, a dining area with a white table and chairs, and a kitchen with white cabinets and a microwave.

8. Salt Shaker Deli & Inn

Salt Shaker Deli & Inn
3.5 star property
Lunenburg Waterfront
8.8 out of 10, Excellent, (321 reviews)
"Nice place!"
Canada
Myles
The price is CA $225
CA $257 total
includes taxes & fees
Nov 8 - Nov 9
Salt Shaker Deli & Inn
An indoor swimming pool with a blue slide, lounge chairs, and a red umbrella.

9. Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre
3.5 star property
Cookville
9.2 out of 10, Wonderful, (1,001 reviews)
"Would stay again !"
Canada
Michelle
The price is CA $167
CA $190 total
includes taxes & fees
Nov 20 - Nov 21
Best Western Plus Bridgewater Hotel & Convention Centre
A waterfront restaurant with outdoor seating and a gift shop.

10. The Dockside Inn & Restaurant

The Dockside Inn & Restaurant
3.0 star property
Lunenburg Waterfront
9.0 out of 10, Wonderful, (644 reviews)
"Staff were great and friendly and we had a lovely view of the water."
Canada
Wendy
The price is CA $125
CA $143 total
includes taxes & fees
Nov 29 - Nov 30
The Dockside Inn & Restaurant
A view of a waterfront property with a dock and a small building.

11. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Excellent location with beautiful marina and ocean view from the property. Very well maintained with excellent host Holly."
United States
Cynthia K G.
The price is CA $190
CA $355 total
includes taxes & fees
Nov 24 - Nov 25
Oceanfront Luxury Magical Views Sunset and Sunrise
A hotel room with a large bed, a desk with a television, a chair, and a window with curtains.

12. Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater
2.5 star property
Bridgewater
7.6 out of 10, Good, (1,002 reviews)
"Staff and continental breakfast were great."
Canada
Jeremy
The price is CA $137
CA $161 total
includes taxes & fees
Nov 8 - Nov 9
Days Inn & Conference Center by Wyndham Bridgewater
A wooden deck with a hot tub surrounded by trees.

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

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
9.8 out of 10, Exceptional, (18 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
The price is CA $179
CA $271 total
includes taxes & fees
Nov 15 - Nov 16
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A hotel room with two beds, a desk with a chair, a television, a coffee maker, and artwork on the walls.

14. Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater
2.0 star property
Bridgewater
8.0 out of 10, Very good, (1,001 reviews)
"Clean rooms friendly staff"
Canada
Wayne
The price is CA $112
CA $132 total
includes taxes & fees
Nov 26 - Nov 27
Travelodge by Wyndham Bridgewater
A small cabin with a deck, a door, and a window.

15. 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 CA $179
CA $223 total
includes taxes & fees
Nov 8 - Nov 9
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A residential area with a house, a swimming pool, and a marina with boats.

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

SUN, SAND, OCEAN, in Hubbards. What more do you need?
Hubbards
9.6 out of 10, Exceptional, (25 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is CA $800
CA $1,176 total
includes taxes & fees
Nov 9 - Nov 10
SUN, SAND, OCEAN, in Hubbards. What more do you need?
A deck with a fire pit, outdoor seating, and a view of the ocean at sunset.

17. Lighthouse Lane Cottages

Lighthouse Lane Cottages
2.5 star property
Indian Harbour
10.0 out of 10, Exceptional, (104 reviews)
"Beautiful view! We had a great stay."
Canada
Kiana
The price is CA $195
CA $229 total
includes taxes & fees
Nov 16 - Nov 17
Lighthouse Lane Cottages
A cozy cabin with a rustic interior, a wooden floor, a stove, a chair, and a view of a lake.

18. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.4 out of 10, Exceptional, (10 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
The price is CA $250
CA $372 total
includes taxes & fees
Nov 8 - Nov 9
Mermaid's Retreat - Caribou Lake Cottage!
A wooden deck with a glass-top table, wicker chairs, and a small umbrella.

19. 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.
The price is CA $247
CA $511 total
includes taxes & fees
Nov 7 - Nov 8
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A tented accommodation with a bed, a television, and a view of a body of water.

20. 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
The price is CA $275
CA $377 total
includes taxes & fees
Nov 8 - Nov 9
Luxury lakefront dome with private beach, close to nature and town!
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

Learn more about Chester

Sail the pristine waters around Chester's harbour, where summer regattas showcase colourful boats against the backdrop of historic waterfront homes. Explore the charming village centre with its artisan shops, then ask locals about their favourite seafood spots for authentic Maritime flavours.

See all hotels in Chester
A blue house with a white porch and a flag.

Top reviews in Chester

A pathway leading to a house surrounded by lush greenery and a well-maintained garden.
Miller House By the Bay

Miller House By the Bay

Miller House By the Bay
mahone bay

10/10 Excellent

Margaret is certainly in her element, she makes you feel welcomed from the moment you walk through the door. Her home and property is just amazing and bonus, what’s not to love about the very quaint Mahone Bay. I’m so looking forward to my next visit!!
Canada
Linda
Reviewed June 2, 2025
Miller House By the Bay

Explore a world of travel with Expedia