
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Chester
Top guest favourite

Cottage in Lunenburg
4.99 out of 5 average rating, 78 reviewsA Secluded Lakefront Spectacle
DarleneRating, 5 stars1 day ago
Danny and Lynn's property was everything we hoped for and then some. Exceptionally clean and tidy with beautiful appliances and all new comfortable furnishings and accessories. We loved the view of the lake and the hot tub was a wonderful treat. We all agreed we would love to visit again. Thank you for making our stay so relaxing.
Top guest favourite

Home in LaHave
4.98 out of 5 average rating, 89 reviewsThe Lookout - Cottage
DebbieRating, 5 stars1 week ago
Another wonderful Easter Weekend with family at The Lookout cottage!! The kitchen is fully equipped with everything you need and the large island is awesome! We love the open concept space. Since we had a nice sunny day, we got to enjoy the large deck and all of the outside seating, overlooking the water! The propane fireplace was nice for chilly mornings. Having a full bath and another half bath is so convenient for 4 people! The hosts are very responsive and provided great instructions about check in and how to find the cottage! Would 100% recommend The Lookout and we hope to return!
Guest favourite

Home in Hammonds Plains
4.94 out of 5 average rating, 48 reviewsSerene modern Lakehouse on Golf Course
Salman Bin RashidRating, 5 stars2 weeks ago
Absolutely loved our 12 nights stay at this stunning Airbnb in Halifax! We came as a group of 10 for my brother’s wedding and the house was beyond perfect. The place is massive, clean, elegant, and super private—ideal for a big family gathering. The ground floor living area became our favorite hangout spot, giving us unforgettable family moments. With 5 spacious bedrooms and a driveway that easily fit over 10 cars, we never felt crowded even when we hosted a dinner with friends. The host was outstanding—very responsive and helpful. We had a minor issue with a shower, and they quickly sent over a video to guide us through, which was incredibly thoughtful. Also, when we reported a small accidental damage, the host graciously waived it. That kind of support is rare. Advice for future guests: If you're planning a trip with family or friends, this is hands-down the best place to stay in Halifax. Gorgeous views, amazing walking paths, and everything you need—restaurants, groceries nearby
Top guest favourite

Guest suite in Black Point
4.96 out of 5 average rating, 50 reviewsThe Beachhouse, Lower Level
JoyRating, 5 stars7 months ago
we loved everything about the beach cottage! Everything is as described, with every detail taken care of! Sweet Ethel is a delight!! Easily the best Air BnB we have stayed in! Thank you so much Ethel for making our 10 day stay wonderful! we will be back!!!
Guest favourite

Home in Rose Bay
4.95 out of 5 average rating, 44 reviewsLuxury Oceanfront Cottage-Rose Bay, Lunenburg #2
KelleyRating, 5 stars1 week ago
We stayed in Cabin #2 which was very private at the far end of the cottages. The view is incredible, the hot tub perfect for two and the cabin was spacious and very clean. We loved the rock stairs down to the ocean and loved the dark, star filled sky at night! Dan was very fast with all communication, thank you for the extra coffee! Great, relaxing time at Board & Batten cottage.
Guest favourite

Home in Falls Lake
4.97 out of 5 average rating, 29 reviewsLog Home Luxury
DanielRating, 5 stars7 months ago
We really enjoyed our stay. The location was perfect to visit the surrounding area such as the local Wineries, Lunenburg and Peggy’s Cove. At the end of the day, the log home was the perfect place to relax and enjoy a sunset on the lake. We made great memories this week. Thank you for sharing this beautiful log home with us.
Guest favourite

Guest suite in Lunenburg
4.96 out of 5 average rating, 332 reviewsA Suite Stay!
ClaireRating, 5 stars3 months ago
Lee Ann’s place is wonderful. So much attention has gone into it. It’s very peaceful and close to Mahone bay and Lunenburgh.They even left the Christmas tree up for me. Beautiful. Plus what can I say about the puppas. Two beautiful dogs. As I am a dog lover it’s been heaven I’m in luv with Max . Leeann calls him her Gentle Giant and so he is. Perfick. Thank you Lee Ann I shall pass the word and hope to be back soon.
Guest favourite

Home in Laconia
4.8 out of 5 average rating, 74 reviewsLake front retreat
JamesRating, 5 stars1 month ago
My 3rd time staying at Ross's place - 1st time in the Winter (previous times in the Fall). Lovely place for a peaceful and quiet getaway. Look forward to another stay in the future.
Quick stats about vacation rentals in Chester
Total rentals
50 properties
Nightly prices starting at
$83 CAD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Halifax Vacation rentals
- Lunenburg County Vacation rentals
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- Cresent Beach
- Halifax Citadel National Historic Site
- Hirtle's Beach
- Maritime Museum of the Atlantic
- Rissers Beach Provincial Park
- Crescent Beach, Lunenburg County, Nova Scotia
- Hunts Point Beach
- Cape Bay Beach
- Little Rissers Beach
- Battery Point Beach
- Backmans Beach
- Bayswater Beach Provincial Park
- Atlantic Splash Adventure
- The Links at Brunello
- Halifax Public Gardens
- Halifax Central Library
- Canadian Museum of Immigration at Pier 21
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Beach Meadows Beach
- Moshers Beach
- Pineo Beach
- Moshers Head Beach