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Family-friendly vacation rentals in Chester

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chester family-friendly rentals

Family-friendly home rentals with a hot tub

Cottage in Chester
5 out of 5 average rating, 14 reviews

Quiet Oceanfront Escape with Hot Tub :)

Lee-AnneRating, 5 stars34 months ago
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.
Superhost
A modern living area is showcased, featuring a brown leather sofa with a light striped throw draped over the back. In the background, a sleek kitchen area and dining table are visible, accompanied by a flat-screen television and decorative plants, creating an inviting communal space.
Apartment in Conquerall Mills
4.74 out of 5 average rating, 408 reviews

Scenic Lakefront Suite with Private Jacuzzi

JennaRating, 5 stars3 weeks ago
We had an incredible stay. We have already started discussing rebooking this every year moving forward now.
The exterior of the cottage is framed by lush greenery, featuring a light yellow facade and white trim. Large windows allow ample natural light, and a welcoming entryway is highlighted by steps leading to the door. A gravel path extends through the well-kept lawn.
Home in Ingramport
4.91 out of 5 average rating, 66 reviews

Lakefront Cottage next to ocean beach

RonaldRating, 5 stars8 months ago
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.
A relaxed living area features a futon and armchairs arranged around a small rug. Natural light enters through large windows, with a potted plant positioned by the seating. Exposed beams and wood paneling contribute to the rustic character of the space.
Home in Black Point
4.5 out of 5 average rating, 111 reviews

Pet-friendly seaside escape minutes from the beach

KerriRating, 5 stars4 months ago
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!
A spacious backyard is showcased, featuring a play structure with two green slides and a climbing area. A trampoline sits nearby, surrounded by lush grass and trees, providing a safe and fun area for children's outdoor activities.
Cabin in Mahone Bay
5 out of 5 average rating, 28 reviews

Ripple Cove Cottage- An All Seasons Retreat

HaileyRating, 5 stars8 months ago
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.
Superhost
A spacious jetted tub is positioned in a corner of the room, surrounded by warm-toned tiles. Natural light enters through nearby windows, illuminating the soft wall colors and creating a relaxing environment.
Apartment in Liverpool
4.73 out of 5 average rating, 26 reviews

3rd Floor Downtown Liverpool - 2 person Jacuzzi!

LanvinRating, 5 stars2 weeks ago
Super comfortable and would definitely stay here again!
Guest favorite
A cozy living area is featured, showcasing a dark gray sectional sofa paired with a navy chaise lounge. A round coffee table anchors the space, while a wooden dining set is visible in the background. Natural light fills the room through a window dressed in light curtains.
Loft in Dartmouth
4.91 out of 5 average rating, 255 reviews

Harbour View Loft

KalynRating, 5 stars6 months ago
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 ☺️
Cabin in Barss Corner
5 out of 5 average rating, 23 reviews

Beautiful waterfront cottage on Sherbrooke Lake

DavidRating, 5 stars20 months ago
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

Superhost
A clean bathroom is featured with a marble vanity and a circular mirror above the sink. A white toilet is positioned to the side, and a bathtub with a shower is adorned with a nautical-themed curtain. Shelves hold neatly arranged towels.
Cottage in Prospect
4.68 out of 5 average rating, 31 reviews

Idyllic Ocean Front Nova Scotia Cottage

MelanieRating, 5 stars11 months ago
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!!
Guest favorite
The image showcases a serene coastal landscape at dusk, featuring two cottages nestled amidst lush green meadows. The calm ocean reflects soft hues of pink and blue, while the horizon stretches into the distance, offering a peaceful ambiance typical of the Kingsburg area.
Home in Rose Bay
5 out of 5 average rating, 63 reviews

Ocean View - 'SeaHaven' Cottage

VirginiaRating, 5 stars1 week ago
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!
Superhost
A vintage wooden sideboard displays decorative items and a vase of fresh tulips. A small dining table paired with green chairs occupies the corner, while natural light filters in through a nearby window, creating a bright and welcoming atmosphere.
Apartment in North End Halifax
4.64 out of 5 average rating, 104 reviews

Terrific Flat in Central Halifax

JessicaRating, 5 stars7 months ago
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. :)
Top guest favorite
A light-filled studio layout includes a cozy sleeping area with a queen bed dressed in white linens. A love seat and circular dining table create a welcoming seating arrangement. Wood flooring adds warmth, while decorative wall art enhances the ambiance. Natural light streams through multiple windows.
Apartment in Halifax
4.89 out of 5 average rating, 199 reviews

Halifax Central - Apt /Bachelor-Back Ground Level

JonasRating, 5 stars4 days ago
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!
Guest favorite
A spacious lower living area is designed with a large sectional sofa and a coffee table. A cozy throw is draped over a chair, while a vibrant piece of art complements the exposed brick wall. Light enters through a small window, enhancing the inviting atmosphere.
Home in Halifax
4.89 out of 5 average rating, 71 reviews

Cozy Inn

VincentRating, 5 stars1 month ago
My wife, friends and I had a great time in Nova Scotia and Candace's location was perfect for us.
Top guest favorite
A cozy living space features a modern electric fireplace set within a classic brick chimney. A neutral-colored futon couch is positioned nearby, complemented by a yellow throw pillow. A light wood coffee table and a white storage unit are also visible, creating an inviting atmosphere.
Guest suite in Dartmouth
4.92 out of 5 average rating, 181 reviews

Harbour View Home

BrielleRating, 5 stars2 days ago
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!
Top guest favorite
A living room area features two armchairs in warm tones and a round table displaying a decorative bowl. A wall-mounted television is positioned above the table, while fresh tulips in a vase add a touch of color to the setting. Light extends through a doorway leading to additional areas.
Apartment in North End Halifax
4.93 out of 5 average rating, 114 reviews

Historic Hydrostone flat

LindaRating, 5 stars6 months ago
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

Guest favorite
Cottage in Hunts point
4.89 out of 5 average rating, 122 reviews

Relaxing Oceanfront Retreat- private luxury

CheraRating, 5 stars2 months ago
Stayed here for the second time, beautiful spot even in the dead of winter!
Top guest favorite
An outdoor play structure features swings, a climbing wall, and a slide, all set in a grassy area surrounded by trees. The structure is designed to offer various play options for children, creating an engaging and safe environment.
Home in Nova Scotia
4.9 out of 5 average rating, 41 reviews

The Blue Cottage

Vincent-GuillaumeRating, 5 stars8 months ago
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!!!
Top guest favorite
The historic home is showcased from a distance, featuring a large front porch with white railings and colorful flower pots. The exterior is painted in soft tones, highlighting the architectural details. Surrounding greenery enhances the natural setting of the property.
Home in Pentz
4.94 out of 5 average rating, 70 reviews

Riverhouse in Pentz

FredRating, 5 stars7 months ago
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

  1. Airbnb
  2. Canada
  3. Nova Scotia
  4. Chester
  5. Family-friendly rentals