
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.

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
Had a great stay.

Sweetwood Farm Sweet Cottage - Hottub Goats Nature
My partner and I wanted a quiet getaway to celebrate a milestone. We wanted nature, privacy and rustic farm vibes with a touch of romance. The place was perfect for what we needed, and Heather was so lovely to deal with! The hottub was divine under the rain, and interacting with the goats was magical. Thank you!

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.

Downtown Liverpool - 3rd flr loft Jacuzzi for 2
Super comfortable and would definitely stay here again!

Harbour View Loft
Donna was a wonderful host the whole time I stayed here. From messaging me on the morning of my arrival to meeting me at the location and helping me get in and sorted out. Throughout the week we chatted a few times and she was always responsive if/when I had questions. The location in Dartmouth was easy to find and rather quiet. The privacy that being on the back of the house provides was huge especially because it was warm so I was opening the windows. The unit itself was wonderful and matched the photos of what were on the listing. Everything was clean, comfortable and accessible. I would absolutely stay with Donna again the next time I am in Dartmouth!

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!!

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. :)

Ocean View - 'SeaHaven' Cottage
Catherine's place was excellent and she is a great host! She was very responsive and helpful before, during and after booking. She happily accomodated our special requests. Her place is very thoughtfully designed and stocked with everything you could need (better than any other air bnb I've been to!). Lots of nice personal and local touches as well. It is located in a great area - quiet, beautiful beach, and awesome coastal hike. You will not be disappointed! Thank you, Catherine!

NESTOR'S POINT Riverfront Cottage - Lighthouse Motel & Cottages
We had a great stay in this quaint coastal town of Conquerall Bank along the LaHave River at this cottage. The space provided was ample and the view from the rooms was amazing. We felt very welcomed by Marc and his pup Austin the first day. He told us about many things to do in the area and we highly recommend the Lahave Bakery a short drive away for breakfast. The cottage is very centrally located along Nova Scotias South Shore and was a great relaxing midpoint for our trip to Cape Breton. We were able to explore the area and ended up at Cresent beach around dusk and it was absolutely stunning. Highly recommend this host and property. (note: The cottage is part of the Lighthouse Motel Properties but is secluded and detached from any other guests - all very well maintained and a pleasure to stay at.)

Cozy Inn
We had an incredible trip at Candace's place. The home was stunning and was perfect for our group of 6. If you have the opportunity to book your trip to Halifax here, I would definitely recommend!

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!!!

Historic Hydrostone flat
One of my favourite Air B&B’s to date! Angela was such a thoughtful host and all of her recommendations were incredible (Bar Kismet, The Narrows, parks, breweries, etc). We had our pup and it was the ideal place, especially for wanting to get around mainly on foot. LOVELY neighborhood. We can’t wait to come back!

Harbour View Home
This was a great place to spend a couple days in Dartmouth - the patio and gardens in the back were the highlight and I spent as much time as I could back there. This will be on the list to rent again next time I’m in town.
Family-friendly home rentals with Wifi

Charming In-law Suite Room - Hydrostone Market
NICE PLACE IN A CHARMING RESIDENTIAL AREA OF HALIFAX We had a very good time in Peter's place. Everything we needed was available there, including very friendly and helpful conversations with Peter. We recommend Peter's place for people who enjoy privacy, calm and charming residential area. There is a direct and convenient bus service to downtown (# 7A and 7B).

Main Stay
Wir haben eine Woche im Juni in dieser wunderschönen Ferienwohnung verbracht. Hier sollte man unbedingt mehrere Tage bleiben. Die Wohnung ist blitzsauber, wunderschön dekoriert und sehr gut ausgestattet. Es gibt sogar eine Yogamatte und einen Regenschirm. Für eventuelle Regentage stehen Rätselhefte und Puzzle zur Verfügung, die man dann mit Blick aus dem Fenster genießen kann. In der näheren Umgebung gibt es viele Ausflugsmöglichkeiten zum wandern, schwimmen und spazieren. Restaurants gibt es genügend und alle fußläufig zu erreichen. Auch der Supermarkt ist gleich um die Ecke. Chris bietet sogar Kaffee und Tee an. Es gibt genügend Gewürze in der toll ausgestattenten Küche sodass man sofort mit dem Kochen oder grillen loslegen kann. Das Badezimmer ist mit Shampoo, Conditioner und Waschlotion ausgestattet, sodass der Überseereisende keine Flüssigkeiten einpacken muß! Absolut empfehlenswert!!!

Lily Lakehouse - Relax & Breathe
We had a great girl’s weekend at Dawn’s place! The property is beautiful, the house is spacious and beds were comfy. Dawn was very helpful and a great host. Would definitely stay again!

1 Bedroom Halifax Home with a Great Location
Catherine’s place is exactly as she described. It is clean, well appointed and comfortable. The pull-out couch is the most comfortable one that I have ever slept on and my aunt said that the bed was also very comfy. Catherine has great books, a fabulous selection of games and other thoughtful touches that make it a good place to stay. We sat out on the back patio in the evening and enjoyed the view of the Bedford Basin and Catherine’s pretty garden. The neighbourhood is residential with lots of lovely trees. It’s a great spot!

Sailors’ Paradise - Stevens Cove Guest Quarters
We really enjoyed the view from the deck and the living room . This place is a GEM . Having the beautiful view of the bay and yachts , being so close to the water made our stay that much more enjoyable . The apartment was nicely furnished and well equipped . It was perfect for a short or long stay and we would love to come back again .

Fish Store Cottage on the ocean wharf Hubbards
A truly magical place. Location is ideal to visit so many different towns, trails and excursions. However, starting the morning off on the deck watching the sunrise and then ending the day cooking on the BBQ. The house is fully equipped with every kitchen gadget needed. 3 good sized bedrooms with comfortable mattresses. There is a wonderful community feeling.

Ocean View Loft Overlooking Harbour
Awesome place felt very secured we could walk everywhere. The deck was awesome with spectacular harbor views. The place was very clean and the kitchen is well equipped. The only drawback back was the neighbors were a bit noisy but nothing to loose sleep over. There are two set of stairs to get into the apartment so if you don’t do stairs this is not the place for you, otherwise I STRONGLY recommend for you to book this place!

The Mighty Atlantic Guest House
Great stay at the Atlantic for 9 adults! Beautiful home blending an historic house with modern amenities. 2.5 baths was a blessing on a busy wedding weekend. Highly recommend!
Quick stats about vacation rentals that are family-friendly in Chester
Total rentals
40 properties
Nightly prices starting at
G$16,727 GYD 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
- 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
- Maritime Museum of the Atlantic
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- 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