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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
$226 nightly
The price is $258
Oct 17 - Oct 18
Total with taxes and fees
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
$161 nightly
The price is $184
Oct 21 - Oct 22
Total with taxes and fees
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
$161 nightly
The price is $184
Oct 21 - Oct 22
Total with taxes and fees
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.
$207 nightly
The price is $236
Oct 17 - Oct 18
Total with taxes and fees
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, (60 reviews)
"Beautiful place to stay. Host was very easy to communicate with."
United States
Jeff T.
$144 nightly
The price is $164
Oct 21 - Oct 22
Total with taxes and fees
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.
$307 nightly
The price is $359
Oct 16 - Oct 17
Total with taxes and fees
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.
$332 nightly
The price is $387
Nov 3 - Nov 4
Total with taxes and fees
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
$207 nightly
The price is $243
Oct 21 - Oct 22
Total with taxes and fees
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.
$186 nightly
The price is $217
Oct 22 - Oct 23
Total with taxes and fees
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
$207 nightly
The price is $236
Oct 20 - Oct 21
Total with taxes and fees
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.
$130 nightly
The price is $148
Oct 19 - Oct 20
Total with taxes and fees
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.
$202 nightly
The price is $235
Oct 21 - Oct 22
Total with taxes and fees
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
$241 nightly
The price is $275
Oct 28 - Oct 29
Total with taxes and fees
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
$196 nightly
The price is $223
Nov 15 - Nov 16
Total with taxes and fees
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
$194 nightly
The price is $227
Oct 28 - Oct 29
Total with taxes and fees
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
$418 nightly
The price is $489
Oct 23 - Oct 24
Total with taxes and fees
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, (13 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
$208 nightly
The price is $237
Oct 18 - Oct 19
Total with taxes and fees
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
$328 nightly
The price is $383
Oct 21 - Oct 22
Total with taxes and fees
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.
$161 nightly
The price is $184
Oct 28 - Oct 29
Total with taxes and fees
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
$111 nightly
The price is $128
Oct 19 - Oct 20
Total with taxes and fees
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

The Homeport Motel

The Homeport Motel

8/10 Good
"We stayed 2 nights here and it is very convenient to visit lunenberg. There's a Tim and grocery store right across the street. Room is spacious and clean with comfortable bedding. We enjoyed the stay and will recommend!"
MEI 2-night trip
Posted 3 hours ago
The Homeport Motel

Find out more about Chester Islands

Everything you need to know about Chester Islands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester Islands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester Islands. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester Islands rentals

At Expedia, we put the best Chester Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester Islands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.