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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 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.
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 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, 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
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 stars5 days ago
JP was very friendly and we enjoyed the animals.
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 stars1 week 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, 196 reviews

Harbour View Home

LisaRating, 5 stars1 week ago
Great location and lovely home

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
4.76 out of 5 average rating, 326 reviews

Charming In-law Suite Room - Hydrostone Market

RoumenRating, 5 stars1 week ago
NICE PLACE IN A CHARMING RESIDENTIAL AREA OF HALIFAX We had a very good time in Peter's place. Everything we needed was available there, including very friendly and helpful conversations with Peter. We recommend Peter's place for people who enjoy privacy, calm and charming residential area. There is a direct and convenient bus service to downtown (# 7A and 7B).
Guest favorite
A panoramic view of Mahone Bay is presented, featuring colorful autumn foliage along the water's edge. Reflections of quaint homes can be seen on the calm surface of the marina, enhancing the serene ambiance of the coastal scenery.
Apartment in Mahone Bay
5 out of 5 average rating, 12 reviews

Main Stay

AngelaRating, 5 stars1 week ago
We spent a week in June in this beautiful apartment. You should definitely stay here for several days. The apartment is sparkling clean, beautifully decorated and very well equipped. There's even a yoga mat and an umbrella. For any rainy days, puzzle books and puzzles are available, which you can then enjoy with a view from the window. There are many excursion options for hiking, swimming and walking in the surrounding area. There are plenty of restaurants and all within walking distance. The supermarket is also just behind the corner. Chris even offers coffee and tea. There are plenty of spices in the well-equipped kitchen so you can start cooking or grilling right away. The bathroom is equipped with shampoo, conditioner and washing lotion, so the overseas traveler does not have to pack liquids! Absolutely recommended!!!
Top guest favorite
A wooden dock extends over a calm lake, with a person seated at the edge, silhouetted against a setting sun. The water reflects warm hues of orange and gold, while trees line the distant shore, contributing to a tranquil scene.
Vacation home in Mount Uniacke
4.99 out of 5 average rating, 72 reviews

Lily Lakehouse - Relax & Breathe

NicoleRating, 5 stars1 week ago
We had a great girl’s weekend at Dawn’s place! The property is beautiful, the house is spacious and beds were comfy. Dawn was very helpful and a great host. Would definitely stay again!
Guest favorite
A modern kitchen is highlighted by sleek cabinetry and stainless steel appliances. A central island with high-backed chairs provides an inviting space for dining. Natural light filters through the window, illuminating the counter, which holds a small decorative plant.
Home in Halifax
4.81 out of 5 average rating, 63 reviews

2 Guests, 1 room, 1.5 bath, Entire place, Parking

DarleneRating, 5 stars3 weeks ago
We had a great stay at Sammi’s place! The home was clean, cozy, anduser friendly. The bed was comfortable, and we appreciated the thoughtful touches like fresh towels, coffee, and local recommendations. The location was nice and quiet—close to restaurants and grocery stores. We even had a nice surprise of seeing two deer in the front and back yard. Sammi was very responsive and made check-in and check-out super easy. The only thing to note is that there wasn’t a TV in the living room, which would’ve been nice for relaxing in the evenings. Not a dealbreaker, but worth mentioning. We used our iPad to watch TV as we don't like to watch TV in bed (our preference) so no big deal. Excellent High-speed WiFi. Close to the highway and downtown Halifax. Overall, a wonderful stay. We’d happily come back when we are in Halifax again and recommend it to others!
Guest favorite
A spacious bedroom features a cozy, striped bedding arrangement on a queen bed. Large windows allow natural light to fill the space, adorned with soft blue curtains. A bedside table and lamp complement the decor, while a calming beach-themed artwork graces the wall.
Apartment in North End
4.88 out of 5 average rating, 118 reviews

1 Bedroom Halifax Home with a Great Location

KaitlinRating, 5 stars2 weeks ago
Catherine's place was the perfect spot! it's very private and is a nice big walk out basement with tall ceilings and a beautiful little backyard. it was very clean and had all the amenities that we needed. The kitchenette is small, but if you plan ahead it's very workable. the location is also very convenient - close to downtown.
Guest favorite
A view through double glass doors reveals a serene bay filled with sailboats. The expansive deck is visible, capturing the outdoor space. In the foreground, a coffee cup rests atop a table, adding a sense of relaxation to the scene.
Apartment in Marriotts Cove
4.89 out of 5 average rating, 55 reviews

Sailors’ Paradise - Stevens Cove Guest Quarters

DavidRating, 5 stars8 months ago
We really enjoyed the view from the deck and the living room . This place is a GEM . Having the beautiful view of the bay and yachts , being so close to the water made our stay that much more enjoyable . The apartment was nicely furnished and well equipped . It was perfect for a short or long stay and we would love to come back again .
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 stars10 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.
Guest favorite
A spacious deck features a white adirondack chair, providing a view of Lunenburg Harbour and the surrounding landscape. The calm water reflects the distant green hills and various boats, while a collection of buildings with vibrant rooftops is visible in the foreground.
Loft in Lunenburg
4.88 out of 5 average rating, 204 reviews

Ocean View Loft Overlooking Harbour

AnapilarRating, 5 stars1 week ago
Awesome place felt very secured we could walk everywhere. The deck was awesome with spectacular harbor views. The place was very clean and the kitchen is well equipped. The only drawback back was the neighbors were a bit noisy but nothing to loose sleep over. There are two set of stairs to get into the apartment so if you don’t do stairs this is not the place for you, otherwise I STRONGLY recommend for you to book this place!

Quick stats about vacation rentals that are family-friendly in Chester

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$16,737 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