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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!
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
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 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!!!
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!

Family-friendly home rentals with Wifi

Guest favorite
A cozy living area features wooden ceiling panels and natural light from two windows adorned with light green curtains. A striped futon offers seating and sleeping options. A small table with two folding chairs and a television create a functional space, complemented by a colorful area rug.
Guest suite in North End Halifax
4.76 out of 5 average rating, 320 reviews

Charming In-law Suite Room - Hydrostone Market

OliviaRating, 5 stars2 months ago
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
Guest favorite
The bathroom features a black vanity with a large mirror above and dual sinks. A blue and white geometric shower curtain hangs in front of a tub shower combination. Natural light is available through an adjoining window, with beige tile flooring enhancing the space.
Apartment in South End Halifax
4.86 out of 5 average rating, 305 reviews

1 Victorian Chic Suite - DT, WALK EVERYWHERE!

KeriRating, 5 stars1 month ago
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.
Guest favorite
A clean and simple bathroom features a white toilet and a small sink. A towel rack holds a turquoise towel, and a bath mat in a matching hue lies on the tile floor. Minimal shelves above the sink provide space for personal items.
Apartment in North End Halifax
4.88 out of 5 average rating, 116 reviews

1 Bedroom Halifax Home with a Great Location

MatthewRating, 5 stars6 months ago
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.
Top guest favorite
A children's play structure is nestled among lush greenery and tall trees. Brightly colored slides and climbing equipment stand out against the natural setting. The area is surrounded by a soft layer of grass and mulch, providing a safe play environment.
Townhouse in Halifax
4.95 out of 5 average rating, 57 reviews

Urban Seaside Home

JenniferRating, 5 stars7 months ago
Just loved the location. Beautiful view and close to downtown Halifax!
Guest favorite
The oceanfront chalet is positioned on a natural slope surrounded by greenery and rock formations. Large windows allow for abundant natural light, enhancing the view of the landscape. A wooden deck leads toward the water, creating an inviting connection with nature.
Chalet in West Pennant
4.85 out of 5 average rating, 142 reviews

Stunning Oceanfront near Halifax

KentRating, 5 stars6 months ago
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.
Superhost
A charming blue cottage stands beside a wooden wharf, visible at water's edge. The structure features a balcony overlooking the water. A clear view of the rocky shoreline can be seen in the foreground, reflecting the serene landscape under a bright blue sky.
Cottage in Hubbards
4.88 out of 5 average rating, 78 reviews

Fish Store Cottage on the ocean wharf Hubbards

MRating, 5 stars8 months ago
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.
Top guest favorite
An open kitchen area with wooden beams and light-colored walls is featured. A large island with rustic stools provides ample seating. Modern appliances are integrated into the design, and sunlight streams through multiple windows, illuminating the space and offering views of the outdoors.
Home in Brooklyn
5 out of 5 average rating, 68 reviews

The Mighty Atlantic Guest House

JonathanRating, 5 stars6 months ago
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!
Guest favorite
A rustic kitchenette is featured, including a farmhouse sink on a wooden counter. A small refrigerator is positioned beneath the counter, while open shelving displays decorative items and plants. The separate entrance emphasizes a natural wood door and an inviting atmosphere.
Guest suite in Lunenburg
4.94 out of 5 average rating, 586 reviews

The Cosy Red Roof

NatashaRating, 5 stars2 months ago
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

    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