
Family-friendly holiday 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!

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
Great location and lovely home

Lakefront Cottage on Annis Lake
Wonderful cottage and location. Everything needed was in the cottage.
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
JP was very friendly and we enjoyed the animals.

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.

Luxury Waterfront Living
Great stay! The place is exactly as described and the pictures show. You can’t do better for location! You can walk anywhere downtown and have so many new restaurants just below the condo. There is ample space for everyone and the kitchen is well stocked with pots and pans for cooking at home. Chris was a fantastic host, he answered all my questions promptly and checked in as well. I will definitely come back and wouldn’t hesitate to use Chris to help find me a space.
Quick stats about holiday rentals that are family-friendly in Chester
Total rentals
40 properties
Nightly prices starting at
$134 NZD 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
Wi-Fi availability
40 properties include access to Wi-Fi
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- House rentals Chester
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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
- Bracketts Beach