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

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chester vacation rentals

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

1. 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 ￥20,154
￥26,570 total
includes taxes & fees
Oct 26 - Oct 27
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A wooden deck with a hot tub surrounded by trees.

2. 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, (17 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 ￥20,154
￥32,217 total
includes taxes & fees
Oct 26 - Oct 27
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bedroom with a sloped ceiling, a bed with a patterned bedspread, a bedside table, a nightstand, a lamp, a window, and a door leading to an outdoor area.

3. 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 ￥37,666
￥46,766 total
includes taxes & fees
Nov 1 - Nov 2
Black Forest Cabins
A view of a waterfront property with a dock and a small building.

4. Oceanfront Luxury with Magical Views of Sunset and Sunrise

Oceanfront Luxury with Magical Views of Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is ￥29,161
￥52,392 total
includes taxes & fees
Nov 8 - Nov 9
Oceanfront Luxury with Magical Views of Sunset and Sunrise
A wooden building with a sign reading "The Knot."

5. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is ￥14,260
￥23,701 total
includes taxes & fees
Oct 30 - Oct 31
Red Barn Bed & Breakfast
A small, two-story cabin with a deck, large windows, and a fireplace.

6. 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 ￥20,154
￥26,570 total
includes taxes & fees
Oct 28 - Oct 29
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A sunset view through a window with bare trees and a distant shoreline.

7. 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, (63 reviews)
"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 sandy beach with people walking along the shore.

8. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"This property was comfortable and convenient and we enjoyed our stay here."
United States
Marty
The price is ￥7,836
￥20,207 total
includes taxes & fees
Oct 26 - Oct 27
Downtown Bridgewater Suite near River and Trails
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

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

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Lunenburg
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay. Nice and clean, quiet and peaceful. Amazing yard. Basics were excellent (Bed, Tv & facilities). Definitely recommend."
Canada
Patrick
The price is ￥20,064
￥35,709 total
includes taxes & fees
Nov 3 - Nov 4
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Property grounds

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

Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax
Boutiliers Point
9.8 out of 10, Exceptional, (20 reviews)
"It was cleaned and cozy stay with beautiful lake view"
Canada
Vikrant D.
The price is ￥22,638
￥30,281 total
includes taxes & fees
Nov 4 - Nov 5
Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax
A dock with boats, a clear blue lake, and a forested island.

11. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
The price is ￥28,148
￥44,026 total
includes taxes & fees
Oct 25 - Oct 26
Mermaid's Retreat - Caribou Lake Cottage!
A beach with clear water, a sandy shore, and a forested island in the distance.

12. 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 ￥27,810
￥57,305 total
includes taxes & fees
Oct 24 - Oct 25
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A small white cabin with green trim and a porch, surrounded by greenery.

13. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.2 out of 10, Good, (7 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
The price is ￥28,227
￥37,646 total
includes taxes & fees
Oct 25 - Oct 26
Orchard Cabin #4 - Hubbards Beach
A geodesic dome tent with a wooden frame and a transparent covering, situated in a forested area with trees and a cloudy sky in the background.

14. Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
Chester
9.0 out of 10, Wonderful, (2 reviews)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
The price is ￥31,413
￥40,817 total
includes taxes & fees
Oct 25 - Oct 26
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
A tented accommodation with a bed, two chairs, and a view of a lake.

15. 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 ￥30,907
￥44,732 total
includes taxes & fees
Oct 28 - Oct 29
Luxury lakefront dome with private beach, close to nature and town!
A wooden cabin in a snowy forest.

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

Pet-Friendly Glamping Dome close to Peggy’s Cove!
Seabright
10.0 out of 10, Exceptional, (19 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
The price is ￥28,983
￥38,752 total
includes taxes & fees
Nov 5 - Nov 6
Pet-Friendly Glamping Dome close to Peggy’s Cove!
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.

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Bridgewater
8.6 out of 10, Excellent, (14 reviews)
"A little hard to find as it is not well marked, although the actual unit was great. Clean and had everything we needed for our stay. Centrally located and easy to get where we needed. Would definitely stay again if in the area."
Canada
Alan
The price is ￥21,393
￥37,673 total
includes taxes & fees
Oct 25 - Oct 26
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
A white single-story building with a front door, a mailbox, and a number '10' sign.

18. Coastal Studio Suite Steps from the Ocean | pet friendly

Coastal Studio Suite Steps from the Ocean | pet friendly
Boutiliers Point
The price is ￥16,024
￥22,388 total
includes taxes & fees
Nov 4 - Nov 5
Coastal Studio Suite Steps from the Ocean | pet friendly
A dining table with blue plates, a bottle, and a glass.

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

Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
Boutiliers Point
10.0 out of 10, Exceptional, (1 review)
"Awesome cabin, great staff who were welcoming and helpful. Great location close to all major attractions"
Canada
Christopher
The price is ￥17,815
￥24,491 total
includes taxes & fees
Nov 4 - Nov 5
Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
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.

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

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Bridgewater
8.6 out of 10, Excellent, (8 reviews)
"Great stay, comfortable place, quiet and close to shops. My only recommendation would be to add a photo of the exterior of the place to help identify it, even if it's only added to the check in info. Overall very nice."
Canada
Cheriee
The price is ￥22,519
￥42,153 total
includes taxes & fees
Nov 8 - Nov 9
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
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

Miller House By the Bay

Miller House By the Bay

8/10 Good
"Loved the space - it gave us lots of room. Even had a small selection of DVD movies. Location was great"
Ian 1-night trip
Posted less than an hour ago
Miller House By the Bay

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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.