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 stars36 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.
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 stars9 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.
The rustic cottage sits on a large green lawn, surrounded by mature trees. A balcony is visible on the upper level, and power lines stretch across the horizon under a clear blue sky.
Home in Black Point
4.48 out of 5 average rating, 113 reviews

Pet-friendly seaside escape minutes from the beach

RaymondRating, 5 stars2 months ago
Had a great stay.
Superhost
The cozy studio cottage features a spacious bed adorned with a textured blanket. Natural wood paneling and high ceilings create an inviting ambiance, while soft light is provided by bedside lamps. A welcoming art piece enhances the serene atmosphere, and a window offers a view of the outdoors.
Farm stay in Blockhouse
4.81 out of 5 average rating, 528 reviews

Sweetwood Farm Sweet Cottage - Hottub Goats Nature

JulieRating, 5 stars6 days ago
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!
A serene view of a lake at sunset, featuring soft pink and purple hues in the sky. A small gazebo with a brown wooden deck is visible in the foreground, accompanied by lush green grass and a few scattered rocks along the shoreline.
Cabin in Mahone Bay
5 out of 5 average rating, 28 reviews

Ripple Cove Cottage- An All Seasons Retreat

HaileyRating, 5 stars10 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 historic building features a striking turret and intricate architectural details, including decorative trim and large windows. The exterior is painted in a deep blue hue, complemented by light yellow accents. The structure is positioned at a street corner, with nearby vehicles visible.
Apartment in Liverpool
4.7 out of 5 average rating, 27 reviews

Downtown Liverpool - 3rd flr loft Jacuzzi for 2

LanvinRating, 5 stars2 months ago
Super comfortable and would definitely stay here again!
Guest favorite
A studio loft features a spacious bed with a vibrant pink coverlet and decorative pillows. A brick accent wall adds a touch of texture. Light wood flooring enhances the warmth, while natural light enters through large windows covered by soft curtains, creating a bright and inviting space.
Loft in Dartmouth
4.91 out of 5 average rating, 258 reviews

Harbour View Loft

LaraRating, 5 stars1 week ago
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!
A wooden dock extends over calm lake water, reflecting the gray sky. A person is swimming nearby, while a dog stands at the edge of the dock, gazing into the water. Lush greenery surrounds the scene, enhancing the serene lake environment.
Cabin in Barss Corner
5 out of 5 average rating, 23 reviews

Beautiful waterfront cottage on Sherbrooke Lake

DavidRating, 5 stars22 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 serene coastal scene features a charming cottage set against a backdrop of lush greenery and distant waters. A winding gravel path leads to the cottage, with rocky outcroppings visible in the background, enhancing the natural beauty of the surroundings.
Cottage in Prospect
4.68 out of 5 average rating, 31 reviews

Idyllic Ocean Front Nova Scotia Cottage

MelanieRating, 5 stars13 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!!
Superhost
A dining area is shown with a light wooden table surrounded by green chairs. A large window allows natural light to enter, while a decorative tapestry hangs nearby. A piano and a well-maintained potted plant occupy the corner, complementing the space's inviting atmosphere.
Apartment in North End
4.64 out of 5 average rating, 104 reviews

Terrific Flat in Central Halifax

JessicaRating, 5 stars9 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. :)
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, 64 reviews

Ocean View - 'SeaHaven' Cottage

MadelineRating, 5 stars2 weeks ago
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!
Superhost
A charming cottage is positioned near the water's edge, featuring a set of steps leading to a porch. White outdoor chairs are placed on the grass, with a view of the LaHave River and distant cottages visible across the water.
Cottage in Pleasantville

NESTOR'S POINT Riverfront Cottage - Lighthouse Motel & Cottages

JustinRating, 5 stars97 months ago
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.)
Guest favorite
An inviting movie room features a large sectional sofa with patterned cushions, a comfortable chaise, and a central coffee table. A substantial flat-screen TV is mounted on the wall, complemented by built-in shelves that hold books and decorative items, enhancing the cozy ambiance.
Home in Halifax
4.88 out of 5 average rating, 74 reviews

Cozy Inn

JennaRating, 5 stars1 month ago
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!
Top guest favorite
The modern kitchen features white cabinetry and granite countertops. A stainless steel stove and a microwave are positioned under a hood. A stainless steel dishwasher is present, and a warm wooden dining table is visible in the foreground. Natural light enters through a nearby door.
Apartment in North End
4.93 out of 5 average rating, 120 reviews

Historic Hydrostone flat

NatalieRating, 5 stars2 weeks ago
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!
Top guest favorite
A vibrant garden is visible, showcasing a variety of plants and flowers in full bloom. Green grass is framed by stone pathways, leading to seating areas. In the background, the Halifax Harbour and skyline can be seen under a clear blue sky.
Guest suite in Dartmouth
4.92 out of 5 average rating, 198 reviews

Harbour View Home

EricRating, 5 stars6 days ago
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.
Guest favorite
A scenic view of Annis Lake is framed by two trees, with sunlight reflecting off the water's surface. The foreground is lined with large natural stone steps leading down to a grassy area, providing a serene backdrop for relaxation and outdoor activities.
Cottage in Queens County
4.93 out of 5 average rating, 114 reviews

Lakefront Cottage on Annis Lake

StephenRating, 5 stars2 weeks ago
Wonderful cottage and location. Everything needed was in the cottage.

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 stars4 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, 42 reviews

The Blue Cottage

MarthaRating, 5 stars1 week ago
JP was very friendly and we enjoyed the animals.
Top guest favorite
A clear blue swimming pool reflects sunlight, with colorful pool accessories floating on the surface. Lush green trees and a well-maintained lawn surround the pool area. The historic home is visible in the background, highlighting its charming architecture.
Home in Pentz
4.94 out of 5 average rating, 70 reviews

Riverhouse in Pentz

FredRating, 5 stars9 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.
Superhost
A modern living room features a sectional sofa and an armchair beside a fireplace. Large windows with a geometric shape fill the area with light, while a coffee table holds books and decorative items. A soft area rug complements the hardwood flooring.
Apartment in Downtown Halifax

Luxury Waterfront Living

CynthiaRating, 5 stars1 month ago
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 vacation rentals that are family-friendly in Chester

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$16,728 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

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