
Family-friendly vacation rentals in Chester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Quiet Oceanfront Escape with Hot Tub :)
Such a beautiful AirBnB. It was perfect for our family of 6 adults and 1 infant. Spacious and wonderful views. The kitchen was perfect for preparing meals. Lots of outdoor sitting areas, and we enjoyed the hot tub, outdoor fireplace and canoeing. A great location for exploring Lunenburg, Mahone Bay, and several beaches. Melissa was a wonderful host 😊. You won’t regret staying at Three Sheep’s to the Wind.

Scenic Lakefront Suite with Private Jacuzzi
We had an incredible stay. We have already started discussing rebooking this every year moving forward now.

Lakefront Cottage next to ocean beach
We had the pleasure to stay for the month of August. Great location overlooking a lake, just a short walk to a small quiet beach on the ocean. An old railway track converted to biking/walking path close by. Close to groceries and restaurants. Great location for day trips to Peggy’s cove/Halifax boardwalk/many parks and beaches. The home had everything you need. Just bring your swim trunks and spirit of adventure. We highly recommend a stay at this lovely spot.

Pet-friendly seaside escape minutes from the beach
Michelle's place was exactly what we expected. It even looked larger in real life vs. photos advertised. we loved the enclosed gazebo the hot tub was located in, the large kitchen table with oodles of seating, open floorplan and the small touches that made it feel aesthetically pleasing and cozy. we will be back sometime in the summer!

Ripple Cove Cottage- An All Seasons Retreat
We had an amazing stay at Beth’s place!! Exceeded expectations, you can tell they put a lot of thought in making sure you have everything you need during your stay.

3rd Floor Downtown Liverpool - 2 person Jacuzzi!
Super comfortable and would definitely stay here again!

Harbour View Loft
The place was just as expected, the tub was great and the location was convenient! The highlight was how kind and welcoming Donna was, she was a joy to meet and converse with. Would recommend staying here and will definitely be booking with her again ☺️

Beautiful waterfront cottage on Sherbrooke Lake
Our second summer stay was just as wonderful as the first. More familiar this time, so the whole family felt right at home. Chris was once again very warm and welcoming in his communications. Look forward to our third stay next year if we can be so fortunate.
Family- and pet-friendly home rentals

Idyllic Ocean Front Nova Scotia Cottage
Most of what I'm saying is echoing what other Guests have said - it's all still true for 2024: Morry is great to work with, cottage is clean and well-equipped, the views here are wonderful, beds are comfy and the layout worked well for us with the two main floor bedrooms on opposite sides. The kitchen is a good size and the two full bathrooms are like new. There's a great hike trailhead a stone's throw away and, if you haven't already, you will fall in love with Prospect, NS!!

Ocean View - 'SeaHaven' Cottage
Beautiful house, incredible views from the house and just a short walk to the beach from the house. Lots of games for adults and kids. Very well equipped in terms of plates cutlery etc we did not see any wildlife but we know there were some outdoor nighttime critters because the Easter eggs we hid outdoors for the kids were almost all gone by morning!

Terrific Flat in Central Halifax
This place was just what we needed for our stay in Halifax. We were within walking distance of local restaurants and a cycle shop where we could rent bikes. The inside was cosy, clean, and really made you feel welcome. Andrea was responsive and a lovely host! Would definitely recommend. :)

Halifax Central - Apt /Bachelor-Back Ground Level
Gerry was very communicative leading up to, and throughout the stay. Super cosy place, everything as described, walking distance to everything in the city. Many shops/restaurants just around the corner. Everything was clean and the bed was very comfortable. Thanks!

Cozy Inn
My wife, friends and I had a great time in Nova Scotia and Candace's location was perfect for us.

Harbour View Home
Marilyn’s home is clean and cozy. The beds were super comfy. And the view of the city is beautiful. Would definitely stay here again!

Historic Hydrostone flat
We always feel at home in Angela’s flat. Can’t think of a thing that has ever been lacking to make our visit completely comfortable. We love the neighbourhood which is remarkably quiet, especially considering how close it is to restaurants, public transit and downtown. Looking forward to our next stay!
Family-friendly home rentals with a pool

Relaxing Oceanfront Retreat- private luxury
Stayed here for the second time, beautiful spot even in the dead of winter!

The Blue Cottage
PAM &J.P on été extraordinaires. Nous avons été ravis par notre séjour et sommes tombés en amour avec la Nouvelle-Ecosse. Les animaux étaient un extra inattendus. Gustave va beaucoup s’ennuyer de Maple. Petit commentaire QUI N’EST PAS UNE CRITIQUE. Le réfrigérateur n’est pas très grand alors, ne pas faire une trop grosse épicerie à chaque fois. Nous sommes arrivés avec trop de choses et tout ne rentrait pas. Mais encore une fois ce n’est pas grave. Il y une épicerie pas tres loin. Ça se fait très bien. Faut juste pas prévoir trop longtemps d’avance si vous avez une grosse famille comme la mienne. La piscine est extraordinaire!!!!! Près de pleins de belles plages . Nous avons passé un super beau moment en famille!!!

Riverhouse in Pentz
Fantastic hosts. Dream heritage property with total privacy and a heated pool in a park like setting; we booked that property pretty much every year for the last seven years. Rob and Barb are constantly improving the property, there is always something new to discover, whether it's a new appliance, or a brand new landscaped river frontage inviting you to sit and watch river and ocean life whilst sipping a glass of tasty red provided with the welcome basket. We enjoyed eating out at the Lunenburg restaurants, as much as we enjoyed cooking a delicious meal at their place, which is fully equipped, one can easily cook up a gourmet meal. Golden! And we shall return!! Greetings from Port Lorne, NS, Conny and Fred.
Quick stats about vacation rentals that are family-friendly in Chester
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
910 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
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- Oak Island
- Cresent Beach
- Halifax Citadel National Historic Site
- Hirtle's Beach
- Rissers Beach Provincial Park
- Crescent Beach, Lunenburg County, Nova Scotia
- Maritime Museum of the Atlantic
- Atlantic Splash Adventure
- Lawrencetown Beach Provincial Park
- Hunts Point Beach
- Little Rissers Beach
- Cape Bay Beach
- Battery Point Beach
- Backmans Beach
- Halifax Public Gardens
- Ashburn Golf Club
- The Links at Brunello
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Halifax Central Library
- Bayswater Beach Provincial Park
- Rainbow Haven Beach
- Conrad's Beach
- Beach Meadows Beach