
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
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Other great vacation rentals in Chester

Tanglewood Cabin
Sarah and Peter were wonderful hosts; easy check-in/ check-out, responsive, and friendly! The cabin was everything we could have possibly hoped for for our quiet weekend outside of the city. The kitchen was equipped with everything we needed, the bed was comfortable, and the woodstove made the space feel even more homey, especially during a rainy weekend. We had a lovely weekend and we would definitely love to come back! Thank you for a wonderful stay.

Dome in the Woods
We had a lovely weekend get away stay. The dome had all the necessities as well as a sauna. Lots of wildlife too.

Lakefront Luxury Retreat
We had a truly wonderful stay! Everything was exactly as described — peaceful, clean, and thoughtfully prepared. We especially appreciated the attention to detail — it’s clear that the hosts care deeply about their guests’ experience. The nature around the place is absolutely beautiful, and the quietness made it feel like a real retreat. Thank you for such a lovely atmosphere. We’d be happy to return someday!

The Whale House
Our stay at The Whale House was perfect! Located in the heart of Nova Scotia’s South Shore, this stunning home is a true treasure! It offers breathtaking views of a peaceful dock filled with boats and sailboats. Gretha was a fantastic host—her directions were clear, & her warm, flexible approach to check-in made us feel immediately at ease. Gretha was incredibly responsive & helpful throughout our stay, always just a message away. The home is immaculate & tastefully decorated with charming whale-themed accents. The cozy pillows & unique artwork add character & coastal charm. We loved the spacious kitchen, especially the oversized island where we enjoyed family meals and games. The large entryway, comfy beds, and thoughtful details made it feel like home. The location was ideal—close to beaches, waterside restaurants, shopping, & the famous Shore Club lobster supper. We woke each morning to the sound of song birds! We’re so grateful to Gretha for sharing her beautiful home with us.

Lakefront tinyhome Chester Grant with hot tub
What a perfect getaway for my daughter and I for her prom weekend nights. So peaceful and serene I couldn’t have asked for a better location. The only thing I would say is the Wi-Fi wasn’t super great for us, but we have very old phones and we weren’t very much concerned about it either because we were away to get away not to be on Wi-Fi. Maybe it was working better if we had to try it more than a couple of times but we just threw our phones away and enjoyed what we had there. I highly recommend this place and I would definitely go back.

Beautiful home in picturesque Chester NS
Completely gorgeous home. Top of the line quality and cleanliness. Suzanne was very responsive to our needs and equipped the house based on our requests. Kitchen was large and had every amenity needed. Superb location. Comfortable and very cozy home and very suitable for large or small numbers. I would highly recommend staying here.

Centrally located in the Village of Chester
Ross' place was everything one could ask for when renting an airbnb . It is centrally located in the village, and we were able to walk to all amenities, and beaches. The house itself was a mariner's dream. I really enjoyed the special touches inside the house itself . The galley kitchen with the "crew mess" set of dishes was a really nice nod to those with a mariner's background. The house was clean, spacious and just delightful to sit in and take in the peaceful surroundings. The master bedroom was a spacious calming haven and it has a lovely deck that overlooks a garden and pond in the backyard. Every morning we would have a family of white tailed deer pass through the garden, this you do not see in the city! This was by far the best Airbnb experience my family and I have had. Ross and Cavenaugh are exceptional hosts!

The Narrows Nest
The Narrows Nest was a fabulous place to stay. It is very close to the heart of Mahone Bay and allowed us to travel around different parts of Nova Scotia easily. It is a beautiful house, and we enjoyed every part of it!
Quick stats about vacation rentals in Chester
Total rentals
50 properties
Nightly prices starting at
G$12,553 GYD 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
Frequently Asked Questions
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 10 house rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Chester have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Chester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Chester?
Four-legged friends are welcome in Chester. Choose from more than 10 house rentals for guests traveling with pets.
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- Oak Island
- Cresent Beach
- Crescent Beach, Lunenburg County, Nova Scotia
- Halifax Citadel National Historic Site
- Atlantic Splash Adventure
- Rissers Beach Provincial Park
- Hirtle's Beach
- Cape Bay Beach
- Rainbow Haven Beach
- Bayswater Beach Provincial Park
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Maritime Museum of the Atlantic
- Dauphinees Mill Lake
- Conrad's Beach
- Beach Meadows Beach
- Oxners Beach
- The Links at Brunello
- Halifax Public Gardens
- Halifax Central Library
- Lawrencetown Beach Provincial Park
- Hunts Point Beach
- Battery Point Beach
- Chester Golf Club