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Holiday Rentals in Chester Chester Car Hire Chester Holidays

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

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

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Top Cities in Chester

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

A white and red lighthouse with a clear blue sky in the background.

Two red Adirondack chairs facing a calm lake with a distant shoreline and cloudy sky.

A rocky shoreline with a clear blue lake, mountains in the background, and a forested hill.

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Our top choices for Chester hotels

A hotel with a large outdoor patio area, multiple balconies, and a well-lit entrance.

A pool area with chairs and a lifebuoy, large windows, and a view of the outdoors.

A modern dining area with wooden tables and chairs, large windows offering a view of a lake and bridge, and unique spherical hanging lights.

An aerial view of a marina with boats docked, surrounded by greenery and a large building.

1. Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 star property

Western Shore

8.4 out of 10, Very good, (634 reviews)

8.4/10

Very good

(634 reviews)

"Great place"

"Great place"

Canada

Angela

The price is AU$186

AU$186

includes taxes & fees

1 Nov - 2 Nov

Oak Island Resort & Conference Centre

A view of a waterfront property with a dock and a small building.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a stove. There are two stools and a small table with a lamp.

A marina at dusk with boats docked, a wooden bridge, and a table with potted plants.

A room with a large skylight, a balcony with a wooden railing, and a view of the sea.

2. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

9.2 out of 10, Wonderful, (29 reviews)

9.2/10

Wonderful

(29 reviews)

"Excellent location with beautiful marina and ocean view from the property. Very well maintained with excellent host Holly."

"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 AU$420

AU$420

includes taxes & fees

5 Nov - 6 Nov

Oceanfront Luxury Magical Views Sunset and Sunrise

A wooden deck with a hot tub surrounded by trees.

A compact room with a bed, a small kitchenette, a mirror, a clock, and a shelf with kitchenware.

A cozy cabin room with a bed, a small table, a mirror, and a wall clock.

A wooden deck with a table and chairs, a grill, and a view of trees.

3. 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)

9.8/10

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"

"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 AU$289

AU$289

includes taxes & fees

1 Nov - 2 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

A view from a window overlooking a sunset over a body of water, with trees and a house in the foreground.

A living room with a dark-colored sofa, a wooden dining table, and a flat-screen TV mounted on the wall.

A dining area with a round wooden table, four wooden chairs, a chandelier, and a potted plant.

A wooden deck with red Adirondack chairs and a grill, overlooking a body of water.

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

8.8 out of 10, Excellent, (64 reviews)

8.8/10

Excellent

(64 reviews)

"The owner was fantastic and he was really hospitable and very friendly. Highly Recommended and will come back again."

"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 blue house surrounded by dense green foliage and trees.

A small, single-story house with a blue exterior, a front porch, and a fenced yard.

A blue house with a white window and a white bell-shaped object on the porch.

A living room with a green sofa, a brown armchair, a coffee table, and a TV. There are windows with curtains, an air conditioning unit, and a small table with a remote control.

5. Quiet, peaceful, private country home with a large yard

Quiet, peaceful, private country home with a large yard

Windsor Road

8.0 out of 10, Very good, (15 reviews)

8.0/10

Very good

(15 reviews)

"It was everything we needed for our stay.."

"It was everything we needed for our stay.."

Canada

Jeff S.

Quiet, peaceful, private country home with a large yard

A small cabin with a deck, a door, and a window.

A compact kitchen with a sink, kettle, coffee maker, and storage cabinets.

A two-story wooden cabin with a deck, a covered outdoor area, and a small window.

A cozy wooden cabin room with a bed, a round mirror, and a window.

6. 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)

10/10

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 "

"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 AU$242

AU$242

includes taxes & fees

1 Nov - 2 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

A small white cabin with a porch, surrounded by a gravel path and large rocks.

A narrow hallway with a door on the left, a window with blinds, a small white appliance, and a red chair.

A wooden deck with outdoor furniture, including chairs and a table, under a large umbrella.

A bedroom with a bed, a dresser, and a door leading to a living area with a sofa and a window.

7. Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

Hubbards

9.8 out of 10, Exceptional, (74 reviews)

9.8/10

Exceptional

(74 reviews)

"Great hosts, very friendly and helpful"

"Great hosts, very friendly and helpful"

United States

charlie m.

Ocean front cottage in the heart of Hubbards.

A modern building with a brick facade and large glass doors, overlooking a body of water.

A compact kitchen with a dining area, including a sofa, table, chairs, and modern appliances.

A modern two-story house with a stone retaining wall and a parked car.

A room with a sofa, a table with a floral tablecloth, a door leading outside, and a framed picture on the wall.

8. Brand-new Oceanfront cottage 8 overlooking Peggys Cove.

Brand-new Oceanfront cottage 8 overlooking Peggys Cove.

Hubbards

8.0 out of 10, Very good, (2 reviews)

8.0/10

Very good

(2 reviews)

"Location was close to things"

"Location was close to things"

Canada

Kelly B.

Brand-new Oceanfront cottage 8 overlooking Peggys Cove.

A hotel with a large building and a smaller structure with a row of windows. There is a dock with boats and a body of water in front.

A marina with boats, a parking area, and a grassy area with a pool.

A marina with boats docked, a swimming pool, and a parking area.

A spacious living area with a blue sofa, a glass coffee table, and a view of the kitchen and dining area.

9. Stunning villa at the beautiful Oak Island Resort

Stunning villa at the beautiful Oak Island Resort

Western Shore

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Helped us out in a bind after the devastating storm xoxo"

"Helped us out in a bind after the devastating storm xoxo"

Canada

Margaret

Stunning villa at the beautiful Oak Island Resort

A coastal view with a boat on the water, large rocks, and white columns.

A room with large windows overlooking a lake and forest.

A two-story house with a red roof, situated on a rocky shoreline with a forest in the background.

A modern kitchen with a granite countertop, a dining area with red chairs, and large windows overlooking a scenic view.

10. Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Hubbards

10.0 out of 10, Exceptional, (116 reviews)

10/10

Exceptional

(116 reviews)

"Absolutely stunning! Lovely host and hostess, super comfortable beds, and the most gorgeous view with little seals popping up here and there. Extremely relaxing and close to so many cute towns!!"

"Absolutely stunning! Lovely host and hostess, super comfortable beds, and the most gorgeous view with little seals popping up here and there. Extremely relaxing and close to so many cute towns!!"

United States

Kerry L.

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

A bedroom with a wooden headboard, two bedside tables with lamps, a bed with a grey blanket, and two windows with curtains.

A small house with a red door, a porch with two chairs, and a deck.

A forested area with a wooden deck overlooking a rocky stream.

A cozy living room with a fireplace, a television, and a dining area.

11. Cozy cottage by the river perfect for nature lovers & pet friendly

Cozy cottage by the river perfect for nature lovers & pet friendly

Chester Basin

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Great host! Everything was seamless, well-organized, even our favourite coffee provided! The house was very clean and she thought of literally everything!"

"Great host! Everything was seamless, well-organized, even our favourite coffee provided! The house was very clean and she thought of literally everything!"

United States

Kim F.

Cozy cottage by the river perfect for nature lovers & pet friendly

A lakeside view with docked boats, wooden docks, and outdoor seating.

Living area

Room

Private kitchen

12. TheLowerDeck Oceanfront escape! Paddle Bds,Kayaking

TheLowerDeck Oceanfront escape! Paddle Bds,Kayaking

East Chester

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"SPOTLESS! Beautiful beds, linens, pillows, blankets etc. so comfortable, Views are wonderful, Art and Flora are lovely."

"SPOTLESS! Beautiful beds, linens, pillows, blankets etc. so comfortable, Views are wonderful, Art and Flora are lovely."

Canada

SANDRA

TheLowerDeck Oceanfront escape! Paddle Bds,Kayaking

A modern building with a brick facade and large glass doors, overlooking a body of water.

A calm body of water reflecting a sunset.

A sunset view with a body of water and trees.

A room with a sofa, a dining table, and a view of a body of water through large sliding glass doors.

13. Brand-new oceanfront cottages with unobstructed views of the Atlantic Ocean.

Brand-new oceanfront cottages with unobstructed views of the Atlantic Ocean.

Hubbards

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"What a view"

"What a view"

Canada

Anne M.

Brand-new oceanfront cottages with unobstructed views of the Atlantic Ocean.

A small, two-story cabin with a deck, large windows, and a fireplace.

A cozy wooden cabin room with a bed, a round mirror, and a window.

A modern kitchen with a built-in stove, coffee maker, and a sink. There are wooden cabinets and a wooden countertop.

A compact kitchen with wooden beams, a built-in stove, and a coffee machine.

14. 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)

9.8/10

Exceptional

(17 reviews)

"A lovely accommodation. The hot tub was a definite plus, especially after a day of travelling. Highly recommend this tiny home :)"

"A lovely accommodation. The hot tub was a definite plus, especially after a day of travelling. Highly recommend this tiny home :)"

United States

Marissa H.

The price is AU$242

AU$242

includes taxes & fees

1 Nov - 2 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

A bedroom with a desk, computer, and a view of the sea.

A dining area with a table set for four, wooden chairs, a lace tablecloth, and a view through a window with blinds.

A two-story house with a red roof, a front porch, and a view of the water.

A kitchen with wooden cabinets, a stove, microwave, and a window.

15. Amazing ocean view/ private road/close to bayswater beach.

Amazing ocean view/ private road/close to bayswater beach.

Hubbards

8.6 out of 10, Excellent, (66 reviews)

8.6/10

Excellent

(66 reviews)

"Beautiful view of the water."

"Beautiful view of the water."

United States

Tracy M.

Amazing ocean view/ private road/close to bayswater beach.

A cabin with a large glass door, surrounded by a stone wall and a patio area with outdoor seating.

A modern house with a gravel driveway leading to a wooden door, surrounded by a stone wall and trees.

A modern living room with a large window, a sofa, a wooden coffee table, and a chair.

A modern house with a long, sloped roof, a small deck, and a stone pathway.

16. Peaceful 2-Bedroom Coastal Cottage with Hot Tub

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

Chester

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"Gorgeous place and close to the surrounding communities while also being secluded."

"Gorgeous place and close to the surrounding communities while also being secluded."

United States

Kirsten

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

A modern house with a large deck, a stone wall, and a forest backdrop.

A modern kitchen with a central island, bar stools, pendant lights, and a clock on the wall.

A modern living room with a built-in bench, a television mounted on the wall, and a potted plant on the windowsill.

A modern living room with a large window, a sofa, a coffee table, and a TV.

17. Cozy Oceanfront Escape with Hot Tub

Cozy Oceanfront Escape with Hot Tub

Chester

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Stunning location, clean, comfortable accommodation. We absolutely loved our stay at cliff top lane. The views were incredible!! The accommodation had everything we needed - highly recommended!"

"Stunning location, clean, comfortable accommodation. We absolutely loved our stay at cliff top lane. The views were incredible!! The accommodation had everything we needed - highly recommended!"

Canada

Jessica W.

Cozy Oceanfront Escape with Hot Tub

A wooden deck with lounge chairs and a table, overlooking a calm lake with boats and distant islands.

A dining room with a round table covered in a red tablecloth, surrounded by wooden chairs. There is a chandelier above the table, and the room has large windows with a view of trees and mountains outside.

A wooden staircase leading down to a dock by a calm lake with a house in the background.

A modern kitchen with a wooden countertop, a sink, and a dining area with a table and chairs.

18. Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Chester

9.8 out of 10, Exceptional, (52 reviews)

9.8/10

Exceptional

(52 reviews)

"Right on the water, multiple decks to enjoy the view and sit or lay back. Comfortable cottage, felt homey and had everything you would need. Full working kitchen with dishes, medium sized fridge, great updated shower- so nice! Comfortable bed and slept like a baby! Quiet and tranquil!"

"Right on the water, multiple decks to enjoy the view and sit or lay back. Comfortable cottage, felt homey and had everything you would need. Full working kitchen with dishes, medium sized fridge, great updated shower- so nice! Comfortable bed and slept like a baby! Quiet and tranquil!"

Canada

Lester

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

A deck with outdoor furniture, a patterned rug, and a view of a house with a window.

A dining area with a table and chairs, a ceiling fan, and large windows with a view of a deck and trees.

A living room with a grey sofa, two armchairs, a wooden coffee table, and a grey rug.

A two-story house with a deck and a covered porch.

19. Stillwood Grove - A cozy 2 bed house, Close to Sensea Spa and Coveside Stables

Stillwood Grove - A cozy 2 bed house, Close to Sensea Spa and Coveside Stables

Chester

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"We booked this lovely place for 2 nights in September and we love our stay. The place is in an easy to find, nice and quiet location, was very clean and had everything we needed. It is even nicer than the pictures show and the host Heather is lovely and accommodating as well. We will be back and can only recommend it."

"We booked this lovely place for 2 nights in September and we love our stay. The place is in an easy to find, nice and quiet location, was very clean and had everything we needed. It is even nicer than the pictures show and the host Heather is lovely and accommodating as well. We will be back and can only recommend it."

United States

Nicole B.

Stillwood Grove - A cozy 2 bed house, Close to Sensea Spa and Coveside Stables

The living room is a spacious place, suitable for your small family gathering

The first room is found at the bottom-level and consists of a double-bed.

We make sure that you have everything at your disposal so that you feel like hom

Dining

20. New Country Stay Ross

New Country Stay Ross

New Ross

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Propery had everything we needed ...any questions we had Janet answered right away....such a GREAT home!"

"Propery had everything we needed ...any questions we had Janet answered right away....such a GREAT home!"

United States

John L.

New Country Stay Ross

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.

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

Holiday Inn Express & Suites Halifax - Bedford by IHG

Holiday Inn Express & Suites Halifax - Bedford by IHG

8/10 Good

"Extrêmement dispendieux. Le système WiFi est un peut lent"

Jacques 1-night trip

Posted 2 hours ago

Holiday Inn Express & Suites Halifax - Bedford by IHG

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

10/10 Excellent

"new facility, so everything is still perfect"

Bridget 2-night trip

Posted 15 hours ago

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

Bridgewater Hotel

Bridgewater Hotel

8/10 Good

"I loved the charm of this place. Some may call it run down. It’s not the fanciest place to stay but I"

Mary Ann 1-night trip

Posted 21 hours ago

Bridgewater Hotel

Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

10/10 Excellent

"Great place to stay, Friendly staff and room was excellent"

jimmy 1-night trip

Posted 1 day ago

Best Western Plus Bridgewater Hotel & Convention Centre

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

10/10 Excellent

"Great place on the ocean. We had cool weather so a patio heater would b a great addition."

Lori S. 5-night trip

Posted 3 days ago

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Comfort Inn Halifax - Bedford Basin

Comfort Inn Halifax - Bedford Basin

10/10 Excellent

"Rooms were clean and comfortable and we had a great view of harbor. Breakfast was very good and the staff were super helpful."

Jolynn 2-night trip

Posted 3 days ago

Comfort Inn Halifax - Bedford Basin

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

10/10 Excellent

"Room was very clean and excellent staff. They served a delicious breakfast and we enjoyed the live entertainment and amenities! We will return"

Niki 1-night trip

Posted 4 days ago

Oak Island Resort & Conference Centre

Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

10/10 Excellent

"."

TERESA 1-night trip

Posted 5 days ago

Days Inn & Conference Center by Wyndham Bridgewater

Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

10/10 Excellent

"We loved the cottage and its convenient location for all our excursions on the south shore. It was cozy, clean and quiet. The mattress was really comfortable. We would definitely stay again."

Kate W. 7-night trip

Posted 2 weeks ago

Ocean front cottage in the heart of Hubbards.

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