Chester Vacation Rentals from AED 325: Search Short-Term Rentals

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chester vacation rentals

A rectangular swimming pool with a deck area, surrounded by a wooden deck, a small building, and various outdoor furniture.

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

Chester

A wooden deck leading to a small cabin with a dark door, surrounded by trees.

2. Black Forest Cabins

Mahone Bay

Julie

AED 680 total

includes taxes & fees

15 Nov - 16 Nov

A marina with boats docked, calm water, and a clear sky.

3. Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

Cynthia K G.

AED 881 total

includes taxes & fees

13 Dec - 14 Dec

A wooden deck with a hot tub surrounded by trees.

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

Windsor Road

Sandra

AED 519 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Chester Basin

Leslie B.

AED 546 total

includes taxes & fees

22 Nov - 23 Nov

A gazebo with a white roof and white railings, surrounded by a dock with chairs and tables.

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

Hubbards

Angela C.

AED 3,005 total

includes taxes & fees

30 Nov - 1 Dec

A wooden deck with a built-in sofa and ottomans, surrounded by lush greenery.

7. The Margaret of Hubbards Apt 2 - 7 Person Hot Tub

Hubbards Nova Scotia

Denis

AED 1,712 total

includes taxes & fees

5 Dec - 6 Dec

A wooden deck with a table and chairs overlooking a lake.

8. Mermaid's Retreat - Caribou Lake Cottage!

Mahone Bay

Josh

AED 957 total

includes taxes & fees

15 Nov - 16 Nov

A dome-shaped building with a central skylight, surrounded by a circular pathway and illuminated by string lights.

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

Lunenburg

Sandie

AED 970 total

includes taxes & fees

15 Nov - 16 Nov

A beach with clear water, a sandy shore, and a forested island in the distance.

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

Ingramport

Victoria W.

AED 1,313 total

includes taxes & fees

15 Nov - 16 Nov

A covered porch with glass doors, a stone staircase, and a view of a garden.

11. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Lunenburg

Patrick

AED 717 total

includes taxes & fees

20 Nov - 21 Nov

A beach with clear water, a rocky shoreline, and a forested island in the distance.

12. Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

Boutiliers Point

Vikrant D.

AED 664 total

includes taxes & fees

27 Nov - 28 Nov

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

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

Chester Basin

Marissa H.

AED 546 total

includes taxes & fees

15 Nov - 16 Nov

A wooden cabin and a geodesic dome structure with seating and a fire pit, surrounded by a forest.

14. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Seabright

Judy

A wooden building with a sign reading "The Knot."

15. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

AED 512 total

includes taxes & fees

18 Nov - 19 Nov

A wooden cabin with a wood-burning stove, benches, and a view of the water.

16. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

Boutiliers Point

Joanna

AED 755 total

includes taxes & fees

27 Nov - 28 Nov

A living room with a sofa, a table with a plant, and a window with blinds.

17. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Bridgewater

Christina

AED 820 total

includes taxes & fees

4 Dec - 5 Dec

A dining area with a wooden table, chairs, and a chandelier. There is a living room with a sofa and a TV in the background.

18. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Bridgewater

Cheriee

AED 917 total

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with a wooden countertop, a built-in sink, and a tiled backsplash.

19. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

Boutiliers Point

Christopher

AED 534 total

includes taxes & fees

27 Nov - 28 Nov

A room with a teal armchair, a blue chest of drawers, a wooden cabinet, a mirror, and a shelf with books and decorative items.

20. King Bed Apt in Bridgewater near River and Trails

Bridgewater

Cassandra W.

AED 582 total

includes taxes & fees

1 Dec - 2 Dec

View all properties

Find vacation rentals that suit your style

Top Chester Hotel Reviews

A pathway leading to a house surrounded by lush greenery and a well-maintained garden.

Miller House By the Bay

mahone bay

10/10 Excellent

Joan

A two-story house with a covered porch, a front yard with a lawn, and a driveway.

Rose & Thistle Bed & Breakfast

Lunenburg

10/10 Excellent

Yaitza

A two-story house with a gabled roof and a front porch.

Fairmont House Bed & Breakfast

Mahone Bay

10/10 Excellent

Earl

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

Oak Island Resort & Conference Centre

Western Shore

10/10 Excellent

Jackie

Black Forest Cabins

Mahone Bay

10/10 Excellent

Janet

A hallway with a white door leading to a room with a view.

The Homeport Motel

Lunenburg

10/10 Excellent

Best place we have stayed at on this trip. The gentleman at the desk was friendly and very helpful. Our room was just remodeled. Bathroom was very roomy, new big tile shower with water that is hot not lukewarm. Comfortable beds with big fluffy pillows and big fluffy towels. It even had real coffee cups and wine glasses plus plates and bowls. Nicer than some of the name brand chains we have stayed at. I would definitely recommend. The gentleman at the desk told us where to go for dinner and the...

Jennifer

An indoor swimming pool with a blue slide, lounge chairs, and a red umbrella.

Best Western Plus Bridgewater Hotel & Convention Centre

Cookville

10/10 Excellent

Wonderful, wonderful experience. The restaurant was fantastic, check in was a breeze, the room was clean and well taken care of. But, above all else, the staff at the check in counter were amazing. We had a one night reservation but got stuck in the huge and horrible July rain/thunder storm. Roads were closed down due to flooding and unsafe road conditions and the threat of a dam breaching. The wonderful young ladies took great care of us by extending our reservation by 2 more nights and even...

Laura

A harbor with boats and colorful buildings.

Rum Runner Inn

Lunenburg Waterfront

10/10 Excellent

Tim

A wooden pier with yellow Adirondack chairs and a sailboat docked.

Bluenose Lodge

Lunenburg

10/10 Excellent

John

Frequently Asked Questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals close to the most popular sights in Chester, or you can choose a secluded option if you'd like a relaxing place to stay. Chester is known for its golf courses and theaters. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best vacation rentals in Chester?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This vacation home rental outside Chester is located by the ocean and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Chester?

Choose from 16 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Cultural attractions to visit include Chester Playhouse and Lordly House Museum. Chester Art Center and Chester Golf Club are other places to visit while you're in town.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

Chester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester vacation rentals

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

2. Black Forest Cabins

3. Oceanfront Luxury Magical Views Sunset and Sunrise

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

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

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

7. The Margaret of Hubbards Apt 2 - 7 Person Hot Tub

8. Mermaid's Retreat - Caribou Lake Cottage!

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

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

11. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

12. Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

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

14. Pet-Friendly Glamping Dome close to Peggy’s Cove!

15. Red Barn Bed & Breakfast

16. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

17. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

18. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

19. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

20. King Bed Apt in Bridgewater near River and Trails

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Miller House By the Bay

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Chester?

What are some of the best vacation rentals in Chester?

How many vacation rentals will I find in Chester?

What’s there to see and do in Chester?

What’s a vacation rental in Chester like?