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.

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Guest favorite
An open-plan living area features a cozy sofa with decorative cushions, a wooden coffee table, and a bar-like seating area with tall stools. Stairs lead to a lofted sleeping area, and large windows provide natural light, highlighting the rustic wooden finishes throughout the space.
Tiny home in Lunenburg
4.97 out of 5 average rating, 371 reviews

Birch tree abode-Bunkie with dry/wet CEDAR SAUNA

Welcome to ‘Birch Tree Abode’. A unique way to unwind after a day in lunenburg county.Situated between Lunenburg and Mahone bay. Minutes from either. This bunkie’ is situated amongst the trees, with comfortable deck to enjoy the beginning/end of your adventures around the South Shore. A beautiful open plan living space, high end bathroom, all rustically finished . 400sq ft-this is slightly larger than a ‘tiny home’, however minimal space 4 storage/luggage ,also note 5.10 ceiling in bedroom area

Top guest favorite
A spacious great room features large windows, allowing natural light to fill the space. A central fireplace with a wooden mantle serves as a focal point, complemented by soft seating arrangements including a light-colored sofa and a blue accent chair. Light-hued curtains frame the windows, providing a calming atmosphere.
Villa in Chester
4.93 out of 5 average rating, 134 reviews

Chester Oceanfront Luxury Villa

Welcome to Skipper Hill, where you will find this stunning villa nestled in the corner of the community, on a 178' oceanfront lot! Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find a selection of restaurants, cafes, and shops sure to please any discerning traveller. Our villa was professionally built and decorated in 2020, thoughtfully prepared for both short and long stays. You'll love the uninterrupted ocean views, countless windows capturing the ocean

Top guest favorite
The cabin is elevated on stilts, surrounded by lush greenery. A wooden porch with chairs offers outdoor seating, while smoke rises from a metal chimney. The structure features large front windows, providing a view of the tranquil forest setting.
Treehouse in New Germany
4.99 out of 5 average rating, 206 reviews

The Bear’s Den treehouse lodging.

Nestled in the woods, accessible year round. Very private & quiet. No hunting on this property but enjoy great fishing. Pizza & burger take-out just 10 min away. Lots of water close by for kayaking/canoeing. ATV trails just a few km away. Firewood supplied. Please bring your own drinking / wash water. Pets welcome, but Not on the furniture unless you’ve brought a cover. Never leave pets unattended. No running water. Outhouse/toilet facility. Bring your own disposable propane tank if BBQ’ing.

Guest favorite
A yurt with a red door is situated amidst a serene forest environment, surrounded by bare trees. The structure features a smooth, white exterior, with a chimney rising from the center. A natural path leads to the entrance, enhancing its rustic charm.
Yurt in Blockhouse
4.76 out of 5 average rating, 103 reviews

Farmstay Yurt

A simple cozy accommodation on an 30 acre off grid farm in Blockhouse. We are a walk from a large trail system where you can easily walk to the local organic cafe: Chicory Blue for a wholesome breakfast or lunch. This 20'' yurt is set right next to a flowing creek with its own modest kitchenette including small propane oven and a solar fridge. The farm is home to 1 horse, pony, 10 sheep, 2 peacocks, Angora bunnies, chickens, kunekune pigs, goats and a large greenhouse and vegetable garden.

Top guest favorite
The exterior of a cottage is surrounded by lush greenery and features a circular swimming pool. Colorful flowers and shrubbery line the walkway, leading to wooden lounge chairs and a shaded umbrella. A fire pit area is visible, inviting outdoor gatherings.
Tiny home in Nova Scotia
4.97 out of 5 average rating, 239 reviews

Cozy Cottage on South Shore. 30 min from Halifax!

A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

Top guest favorite
An outdoor pizza oven sits under a large orange umbrella. A wooden countertop surrounds the oven, which is complemented by a stacked wood storage underneath. Nearby, a small red table holds potted flowers, enhancing the garden's green backdrop.
Apartment in Bridgewater
4.95 out of 5 average rating, 385 reviews

'Breeze from LaHave'-Cozy&Modern Walkout Basement

* COVID-19 quarantine not accepted. * 'Breeze from LaHave' is a bright & cozy walkout basement suit, entirely used for guests. It is located at the hub of scenic South Shore, reaching major tour destinations within 20 minutes, such as Lunenburg, Mahone Bay, enjoying the convenient amenities & services of hub town such as Hospital, mall, cafes, restaurants and banks, all within 5min walking. If you like walking in woods, Centennial Trail is directly connected to our Airbnb backyard.

Top guest favorite
A charming boathouse is positioned on a wooden dock, surrounded by lush greenery. The elevated deck features a glass railing, offering unobstructed views of the water. Two wooden benches provide seating, inviting relaxation in the serene seaside setting.
Cottage in Chester
4.95 out of 5 average rating, 105 reviews

The Boathouse on Scotch Cove

This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

Top guest favorite
A serene lakefront scene captures vibrant autumn foliage reflecting on still waters. A wooden boardwalk leads to a small dock, surrounded by trees displaying shades of red, orange, and green, creating a peaceful natural setting.
Guest suite in Hubbards
4.96 out of 5 average rating, 265 reviews

Studio Suite Apt at Cove Cottage Eco Oasis

We're a lakefront eco-retreat tucked into the woods, 45 mins from HRM. Walk the boardwalk, sit lakeside enjoying the views or enjoy the ducks & chickens. Star-watching is a must! Your stay includes a DIY Breakfast bar: Buttermilk pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea. We are scent free and all natural with 100% cotton bedding! Studio Suite is an Apartment here in our main building, more detail ⬇ Find us on TT, IG & FB: covecottageecooasis

Top guest favorite
A spacious bedroom features large windows allowing natural light to fill the room. A comfortable bed is centered, with a modern fan above. A foosball table adds recreational space, while a closet and additional storage are present, accentuated by soft-colored walls and tasteful furnishings.
Apartment in Mahone Bay
4.97 out of 5 average rating, 105 reviews

Guest accomodation in Mahone Bay town

Beautiful suite in quiet, central area of Mahone Bay. Steps to main street but away from the traffic and backing onto the park. The suite is one wing of a large, older historic home. The property is in the heart of one of the South Shore's most picturesque seaside towns. The property is about 1 hour from Halifax and the airport and is walkable to many restaurants, stores, the harbor, and trails. The children's park is steps away, as is the town swimming pool.

Guest favorite
A bright bedroom features a comfortable bed adorned with a colorful quilt. Two windows allow natural light, while built-in shelves display books. A vintage blue trunk is positioned at the foot of the bed, with soft lighting from two bedside lamps creating a cozy environment.
Apartment in Mahone Bay
4.86 out of 5 average rating, 111 reviews

Pleasant Street Suite

Location, location, location! This studio apartment is located in the heart of Mahone Bay. Restaurants, shops, grocery store, pharmacy, and of course the three churches are within a 5 minute walk. The space is colourful and cheery with an east coast vibe. The apartment has a well equipped kitchenette if you prefer to cook light meals yourself. There is also a dining area which could be used as a very comfortable work space. Enjoy our beautiful town!

Top guest favorite
A spacious waterfront deck features comfortable seating arrangements with wicker chairs and a round table. A hot tub is visible to the side, surrounded by greenery. The serene water view is framed by clear skies, offering a peaceful outdoor space.
Home in Lunenburg
4.94 out of 5 average rating, 150 reviews

Ocean Front #12 HotTub PrivateDeck waterfront BBQ

Take it easy at this unique and tranquil getaway.and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Top guest favorite
A spacious living area features a large triangular window wall offering panoramic views of the ocean and surrounding trees. A comfortable couch and a rustic wooden coffee table are positioned near a cozy wood stove. A window seat, adorned with soft pillows and a throw, invites relaxation.
Cottage in Deep Cove
4.99 out of 5 average rating, 118 reviews

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a canopy of starry skies. Overlooking the entrance to Deep Cove, and out towards Chester, Nova Scotia, this secluded four-season cottage offers an idyllic escape, ideal for a romantic couple's getaway or a tranquil retreat from the everyday.

Popular amenities for Chester family-friendly rentals

When is the best time to visit Chester?

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Avg. priceG$31,965 GYDG$31,338 GYDG$30,085 GYDG$30,502 GYDG$37,606 GYDG$44,918 GYDG$54,946 GYDG$54,946 GYDG$48,052 GYDG$45,545 GYDG$37,188 GYDG$36,561 GYD
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Quick stats about vacation rentals that are family-friendly in Chester

  • Total vacation rentals

    Explore 40 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at G$10,446 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,150 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chester rentals

  • 4.9 Average rating

    Chester stays are highly rated by guests—averaging 4.9 out of 5!

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