
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.
Vacation rentals for every style
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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!

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
Outstanding host. Truly blown away by Gerry’s warm welcome to Halifax. Every day he offered assistance and advice, which was much needed and appreciated since we had never been to Nova Scotia before. His friendliness is genuine and heartwarming. And his place is totally fantastic. An unexpected bonus was 100% the best hot water pressure in a shower that I’ve ever experienced in my life. Highly highly recommended.

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

The Blue Cottage
PAM & J.P were extraordinary. We were delighted with our stay and fell in love with Nova Scotia. The animals were an unexpected extra. Gustave is going to miss Maple a lot. Small comment WHICH IS NOT A CRITICISM. The refrigerator is not very big, so don't do too much grocery shopping at once. We arrived with too many things and not everything fit. But again, that's okay. There's a grocery store not far away. It's very easy. Just don't plan too far ahead if you have a big family like mine. The pool is amazing!!!!! Close to lots of beautiful beaches. We had a great time with the family!!!

Harbour View Home
Our stay was better than expected, beautiful location and water front view and garden, it's a bird haven and get place for relaxation. Also the artwork itself throughout the airbnb was an experience. As an artists myself, I absolutely appreciated this and felt inspired by all the original artwork. One can feel the love and thoughtfulness put into creating and designing the space. Lots of extra 's when it comes thoughtfulness from what is in the cabinets from tea, coffee, icecream, tovthe bathroom cabinets, band aids, q tips , feminine pads, and much more.

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 wifi

Charming In-law Suite Room - Hydrostone Market
Really cozy and stylish place, nice amount of light, Peter was very kind, easy going, responsive, and helpful. I would stay here again! I wish this was my apartment hehe

1 Victorian Chic Suite - DT, WALK EVERYWHERE!
We really enjoyed our stay. The suite was well equipped and clean and in good condition. The location is very central and it really was easy to walk everywhere downtown. The temperature was comfortable and there were extra towels and blankets.

1 Bedroom Halifax Home with a Great Location
I had a fantastic time at Catherine's place! She provided plenty of guidance on places to go, and each one was exceptional. She both met me when I arrived and said goodbye when leaving, and she made sure that I had everything I needed. I had to make a sudden last minute change to my booking and she was very accommodating. I would highly recommend staying here.

Urban Seaside Home
Just loved the location. Beautiful view and close to downtown Halifax!

Stunning Oceanfront near Halifax
One of those rare times when a house described as "stunning" really lives up to it. John's house near Halifax is beautiful and serene, all windows and wood and incredible views out to the water in the cove and ocean beyond. Surrounded by trees and a garden path down to the dock, it feels private but not isolated. Great house on the inside also - spotlessly clean, streamlined so there's no clutter but everything you need, simple but quite beautiful also. Comfortable beds, great kitchen and bathrooms and just full of sunlight. Can't imagine a better spot to relax and recharge, and close to lots of good hiking. John is super friendly and responsive, a great host - look forward to coming back.

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.

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!

The Cosy Red Roof
Had a great stay at Kathryn's! The place is lovely, peaceful and quiet. Would definitely recommend to others! :)
Quick stats about vacation rentals that are family-friendly in Chester
Total rentals
40 properties
Nightly prices starting at
$111 CAD 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
- Halifax Vacation rentals
- Lunenburg County Vacation rentals
- Dartmouth Vacation rentals
- Lunenburg Vacation rentals
- Truro Vacation rentals
- Wolfville Vacation rentals
- Bedford Vacation rentals
- Peggy's Cove Vacation rentals
- Mahone Bay Vacation rentals
- Alma Vacation rentals
- Digby Vacation rentals
- Hubbards Vacation rentals
- Rentals with a patio Chester
- Rentals with a fireplace Chester
- Cottage rentals Chester
- Pet-friendly rentals Chester
- Rentals with a washer and dryer Chester
- Cabin rentals Chester
- Rentals with outdoor seating Chester
- House rentals Chester
- Rentals with beach access Chester
- Family-friendly rentals Nova Scotia
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- 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
- Hunts Point Beach
- Little Rissers Beach
- Cape Bay Beach
- Battery Point Beach
- Backmans Beach
- Bayswater Beach Provincial Park
- Atlantic Splash Adventure
- Canadian Museum of Immigration at Pier 21
- Halifax Central Library
- The Links at Brunello
- Halifax Public Gardens
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Beach Meadows Beach
- Moshers Head Beach
- Oxners Beach
- Old Town Lunenburg