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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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Chester Accommodation: Most Popular Cities to Stay

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 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.

A lakeside view with several boats docked at a marina, surrounded by turquoise Adirondack chairs and a small fire pit.

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

1. 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)

8.4/10

Very good

(638 reviews)

"Great place"

"Great place"

Canada

Angela

The price is £98

£98

includes taxes & fees

4 Nov - 5 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 room with a large skylight, a balcony with a wooden railing, and a view of the sea.

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

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 £197

£197

includes taxes & fees

15 Nov - 16 Nov

Oceanfront Luxury Magical Views Sunset and Sunrise

A wooden deck with a hot tub surrounded by trees.

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

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

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 £147

£147

includes taxes & fees

2 Nov - 3 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

A sunset view through a window with bare trees and a distant shoreline.

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

A laundry room with a front-loading washer and dryer, wooden paneling, a window, and a shoe rack with shoes.

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

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, (65 reviews)

8.6/10

Excellent

(65 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, single-story cabin with a porch, a covered outdoor area, and a well-maintained garden.

A small blue house surrounded by dense green foliage and trees.

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.

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

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)

"Nothing nice about it , run down clogged drains, dirty windows, floor , limited kitchen supplies. Cheaper than average I guess"

"Nothing nice about it , run down clogged drains, dirty windows, floor , limited kitchen supplies. Cheaper than average I guess"

United States

Mike H.

Quiet, peaceful, private country home with a large yard

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 neatly made bed with a patterned bedspread and pillows, a bedside table with a book, and a door leading to a bathroom.

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

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

A compact kitchen with white cabinets, a stove, and a refrigerator. There is a window with blinds, a ceiling fan, and a couch with green pillows.

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

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

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 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.

8. 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 £121

£121

includes taxes & fees

2 Nov - 3 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

Room

Private kitchen

Living area

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

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.

A kitchen with granite countertops, a dining area with a table and chairs, a staircase, and a view of the ocean through large windows.

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

A patio with wicker furniture, a glass-top table, and a view of boats and water.

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

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

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

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.

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

A neatly made bed with a patterned bedspread and pillows, a bedside table with a book, and a door leading to a bathroom.

A sunset view with a body of water and trees.

A calm body of water reflecting a sunset.

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 small cabin with a wooden deck, stone pathway, and a view of the surrounding forest.

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

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

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 £121

£121

includes taxes & fees

2 Nov - 3 Nov

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

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

A bedroom with a bed, a wooden door, and a view of the sea through a glass door.

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

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, (67 reviews)

8.6/10

Excellent

(67 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 wooden deck with lounge chairs and a table, overlooking a calm body of water with a distant island.

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

A living room with a TV, a blue sofa, a yellow armchair, and a window with a view of greenery.

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

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

A modern building with a black exterior, a wooden panel section, and a tiled patio area.

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

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

A modern interior with a large window overlooking the sea, a dining area, and a seating space.

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

18. 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

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.

Dining

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

19. 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

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

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

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

A kitchen with white cabinets, a microwave, a toaster, a kettle, and a coffee maker.

20. 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

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

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

10/10 Excellent

"We stayed for one night and it was great. The hotel was very pleasing and clean. Our room was clean with a huge space for our stuff. The breakfast food was delicious and had so many options to choose from. Overall this hotel was the best one we have ever stayed in, and we’ll be back that’s for sure! Thank you."

Rejeann 1-night trip

Posted 4 hours ago

Halifax Tower Hotel & Conference Centre, an Ascend Collection Hotel

Future Inns Halifax

Future Inns Halifax

10/10 Excellent

"My favourite place to stay!!"

Sally 1-night trip

Posted 4 hours ago

Future Inns Halifax

Old Orchard Inn

Old Orchard Inn

10/10 Excellent

"Friendly staff and well maintained property."

Christian 1-night trip

Posted 10 hours ago

Old Orchard Inn

Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

10/10 Excellent

"nice and friendly staff, room was spotless had a great stay"

Jazmyne 1-night trip

Posted 22 hours ago

Best Western Plus Bridgewater Hotel & Convention Centre

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

10/10 Excellent

"Great place"

Michelle 1-night trip

Posted 2 days ago

Chateau Bedford, Trademark Collection by Wyndham

Stardust Motel Bedford

Stardust Motel Bedford

10/10 Excellent

"Staffs were very accommodating. Rooms was clean and tidy."

Judilyn 5-night trip

Posted 3 days ago

Stardust Motel Bedford

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 6 days ago

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

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 3 weeks ago

Ocean front cottage in the heart of Hubbards.

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