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Chester Islands Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester Islands vacation rentals

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.

1. 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 ￥37,498
￥46,558 total
includes taxes & fees
Oct 20 - Oct 21
Black Forest Cabins
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, (16 reviews)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Canada
Carol
The price is ￥22,280
￥29,082 total
includes taxes & fees
Oct 25 - Oct 26
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small cabin with a deck, a door, and a window.

3. 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 ￥22,280
￥29,082 total
includes taxes & fees
Oct 25 - Oct 26
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bright living room with a white sofa, a coffee table, and a potted plant.

4. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (118 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
One bedroom fully equipped Mahone Bay luxury cottage
A sunset view through a window with bare trees and a distant shoreline.

5. 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, (61 reviews)
"We enjoyed our stay. Property was as described, we especially enjoyed the view."
United States
Sandy e.
The price is ￥20,052
￥26,415 total
includes taxes & fees
Oct 25 - Oct 26
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A beach with clear water, a sandy shore, and a forested island in the distance.

6. 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, (122 reviews)
"Great location and beautiful spot. Our family of 5 really enjoyed our visit!!"
United States
Victoria W.
The price is ￥27,601
￥57,001 total
includes taxes & fees
Oct 18 - Oct 19
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A view of a waterfront property with a dock and a small building.

7. 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, (28 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is ￥32,406
￥56,561 total
includes taxes & fees
Oct 20 - Oct 21
Oceanfront Luxury with Magical Views of Sunset and Sunrise
A wooden cabin in a snowy forest.

8. 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 ￥28,853
￥38,578 total
includes taxes & fees
Oct 27 - Oct 28
Pet-Friendly Glamping Dome close to Peggy’s Cove!
A sauna with a view of the sea, wooden walls, and a stone heater.

9. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Boutiliers Point
9.6 out of 10, Exceptional, (27 reviews)
"Check in staff were very friendly and showed us around the cabin and facilities. Cabin was clean, had all required items for cooking and enjoying the stay."
United States
Kristopher H.
The price is ￥25,734
￥34,408 total
includes taxes & fees
Oct 27 - Oct 28
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

10. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (114 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is ￥22,349
￥37,453 total
includes taxes & fees
Oct 20 - Oct 21
Mahone Bay Hide-Away
A wooden building with a sign reading "The Knot."

11. 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 ￥14,153
￥23,523 total
includes taxes & fees
Oct 20 - Oct 21
Red Barn Bed & Breakfast
A small white cabin with green trim and a porch, surrounded by greenery.

12. 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 ￥28,015
￥37,364 total
includes taxes & fees
Oct 18 - Oct 19
Orchard Cabin #4 - Hubbards Beach
A dock with boats, a clear blue lake, and a forested island.

13. 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 ￥27,850
￥43,560 total
includes taxes & fees
Oct 25 - Oct 26
Mermaid's Retreat - Caribou Lake Cottage!
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

14. 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 ￥19,913
￥35,440 total
includes taxes & fees
Nov 2 - Nov 3
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
A dining table with blue plates, a bottle, and a glass.

15. 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 ￥26,970
￥36,113 total
includes taxes & fees
Oct 30 - Oct 31
Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
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)
"Sweet location. Easy check-in via lockbox. Had everything we needed. Clean. Only area for improvement is the pullout sofa. Mattress not usable. Two main bedrooms were great."
Canada
Sue
The price is ￥44,003
￥77,417 total
includes taxes & fees
Oct 23 - Oct 24
SUN, SAND, OCEAN, in Hubbards. What more do you need?
A calm lake with boats docked at the pier, surrounded by trees.

17. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.4 out of 10, Exceptional, (14 reviews)
"Really enjoyed our stay at the cottage. Was warm and cozy for the duration of our stay. It was so enjoyable that we changed our plans to tour around and stayed at the cottage. Beautiful location."
Canada
Harold
The price is ￥23,333
￥37,682 total
includes taxes & fees
Oct 18 - Oct 19
Lake Mushamush Cottage!
A porch with colorful Adirondack chairs and a wooden deck.

18. Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.8 out of 10, Exceptional, (6 reviews)
"Nothing else to add."
Canada
Blair
The price is ￥45,535
￥60,769 total
includes taxes & fees
Oct 20 - Oct 21
Log Cabin #1 - Hubbards Beach
A small, two-story cabin with a deck, large windows, and a fireplace.

19. 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 ￥22,280
￥29,082 total
includes taxes & fees
Nov 1 - Nov 2
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A sandy beach with people walking along the shore.

20. 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 ￥7,778
￥20,056 total
includes taxes & fees
Oct 18 - Oct 19
Downtown Bridgewater Suite near River and Trails
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 Islands Hotel Reviews

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

10/10 Excellent
"great place to stay"
Mike 1-night trip
Posted 20 hours ago
Oak Island Resort & Conference Centre

Find out more about Chester Islands

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

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

Frequently asked questions

Can I find vacation rentals in Chester Islands?

Yes, you can find vacation rentals close to top points of interest in Chester Islands, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Chester Islands has to offer?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: Visitors like this Chester Islands vacation home rental. It 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.

What’s there to see and do in Chester Islands?

Explore the area and family-friendly sights such as Shore Club Dance Hall, or get out into nature at a spot like Oak Island. In the larger area, you’ll find Chester Golf Club and Chester Art Center.

What’s a vacation rental in Chester Islands like?

Vacation rentals are private properties you can book for several days or longer in Chester Islands. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.