Chester Islands Holiday Rentals from NZ$295: Search Short-Term Rentals

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Our top choices for Chester Islands holiday rentals

A wooden deck with a hot tub surrounded by trees.

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

Windsor Road

Carol

includes taxes & fees

18 Oct - 19 Oct

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

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

Chester Basin

Suzanne

includes taxes & fees

13 Oct - 14 Oct

A bright living room with a white sofa, a coffee table, and a potted plant.

3. One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay

Dianne T.

includes taxes & fees

17 Oct - 18 Oct

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

4. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Hubbards

Joanne

includes taxes & fees

20 Oct - 21 Oct

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.

5. Black Forest Cabins

Mahone Bay

Julie

includes taxes & fees

12 Oct - 13 Oct

A sandy beach with people walking along the shore.

6. Downtown Bridgewater Suite near River and Trails

Bridgewater

Marty

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

7. Mahone Bay Hide-Away

Mahone Bay

Richard

includes taxes & fees

20 Oct - 21 Oct

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

8. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

includes taxes & fees

19 Oct - 20 Oct

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Top Chester Islands Hotel Reviews

Clifty Cove Motel

10/10 Excellent

"Room was clean and comfortable."

Miller House By the Bay

8/10 Good

"Miller house was great. Our room was very large, loved the king bed. Margaret made us a great breakfast. The location was awesome very walkable. I would say the only thing I would say is that I did not realized it was a shared bathroom. I did not see anything in the bed and breakfast information about that. I probably would not have stayed there but that is just me. The one bathroom upstairs is very large and clean. Personally it’s not a choice I would have made. Otherwise beautiful place."

The Tuna Blue Inn and Restaurant

10/10 Excellent

"The Tuna Blue is charming, well maintained, quiet, and comfortable. We loved the location right on Hubbards Cove and the beautiful view from our room - the terraces are a fantastic amenity. The building is very cool and it feels like you’re staying in someone’s big old house. We had a delicious dinner at the restaurant and waitstaff were friendly and efficient. We never actually met a staff member from the Inn, which wasn’t a problem (nice that they trusted us to check ourselves in and out!). They don’t offer breakfast but the in-room coffee was excellent - though we would have liked the opportunity to get a second cup! In fact we think one improvement they could make would be to use a downstairs common room for a guest coffee station (and a few muffins in the morning wouldn’t hurt!). Our bathroom was fine though a bit dated and the shower light didn’t work, and our room could’ve used a rug. But overall we loved the place and would stay there again!"

Surfside Inn

8/10 Good

"We stayed in the honeymoon suite and the king bed was amazingly comfortable. The staff were great and helped me with heavy bags up the steep stairs (be ready for that if you’re old or weak). The adjacent beach across the road was quite with hardly anyone on it (romantic). The down side of the room was 3 things: 1) there were only sheers on the windows so privacy at night was a little off and the room was too bright in the morning. 2) the shower stall was ridiculously small - about 24” x 30” so the curtain stuck to my side and the shower head was an old ‘water saver’ head and hardly sprayed much water. 3) the bathroom fan was noisy and requires replacing. The chandelier above the jacuzzi tub made us laugh as we banged our heads on it standing up. Oh and #4 if the owners are reading… replace the window screens! The ocean view is no good blurred by ancient window screens. A nice stay but not worth the money -especially for newlyweds and because I need a nice shower!!"

Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route

10/10 Excellent

"The reviews didn't lie. The cottage is exactly as described. Beautiful peaceful location. Great communication with the host. Everything was neat and clean. I would not hesitate to book again. It was a perfect place for our anniversary trip."

Find out more about Chester Islands

Everything you need to know about Chester Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester Islands holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester Islands holiday rentals we have selected for you start as low as NZ$295 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester Islands rentals

At Expedia, we put the best Chester Islands holiday 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 holiday.

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 holiday rentals in Chester Islands?

Yes, there are holiday rentals close to the most popular sights in Chester Islands, or you can select a more secluded option if you're looking for a relaxing stay.

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

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside of Chester Islands 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Chester Golf Club and Chester Art Center.

What’s a holiday rental in Chester Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester Islands. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family getaway.

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Our top choices for Chester Islands holiday rentals

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

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

3. One bedroom fully equipped Mahone Bay luxury cottage

4. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

5. Black Forest Cabins

6. Downtown Bridgewater Suite near River and Trails

7. Mahone Bay Hide-Away

8. Red Barn Bed & Breakfast

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

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

11. Oceanfront Luxury Magical Views Sunset and Sunrise

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

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

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

15. Orchard Cabin #4 - Hubbards Beach

16. Oceanfront Kayaking retreat close to Lunenburg

17. Lake Mushamush Cottage!

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

19. Pretty Bachelor with Balcony near River & Trails

20. Mermaid's Retreat - Caribou Lake Cottage!

Find holiday rentals that suit your style

Top Chester Islands Hotel Reviews

Clifty Cove Motel

Miller House By the Bay

Atlantic View Motel and Cottages

The Tuna Blue Inn and Restaurant

Rum Runner Inn

Surfside Inn

Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route

Find out more about Chester Islands

Frequently asked questions

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