Family-friendly holiday rentals in Chester

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Top-rated family-friendly rentals in Chester

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Guest favourite
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, 129 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 favourite
A cozy living area features two armchairs and a sofa, arranged around a large area rug. A wooden entertainment unit holds a television, while a fireplace is centered against the wall. Framed art adorns the walls, contributing to a welcoming ambiance.
Apartment in Simms Settlement
4.95 out of 5 average rating, 172 reviews

Quiet, Close to Hwy – Home to Roost – basement apt

Rural. Basement suite in the forest – queen (60 inch) bed. Near Rails to Trails. Kitchen/full bath. Linens. Bedding. Regular refresh. Heat pump and air exchanger. Private entrance. Half hour to Halifax, Bridgewater, Valley. Two minutes to 103 Hwy. No smoking. – Editor/owner will work with writers on retreat for additional hourly cost and prior notice. Laundromat close by. Beaches, museums, liquor store, bank machines, restaurants, pharmacy near by. (GPS: locate 44.629160, -64.084702)

Guest favourite
An open-concept living area showcases a blend of rustic and modern design elements. A wood stove stands beside a large window, allowing natural light to fill the space. Two chairs and a small table create a cozy nook, complemented by sleek cabinetry and polished wooden floors.
Cottage in Martins Point
4.95 out of 5 average rating, 208 reviews

OTW Close 2 Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use tax" are local sales taxes charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins to NORDIC Spa • 10 mins from Mahone Bay & Oak Island • Free bikes with access to the Chester Connection Trail • BBQ, full kitchen and utensils, A/C, cable TV, wifi and parking • Open-concept living • Full bath on the main floor, 2 bedrooms on the second floor • The house is 100 years old so the stairs are steep • Porch has shared laundry facilities for the guesthouse next door

Top Guest favourite
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, 237 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 favourite
A cozy sleeping area features a spacious bed with sloped ceilings above. A comfortable sofa and an accent chair are arranged over a vibrant, textured rug. Natural light filters through a large, arched window, illuminating the rustic wooden floors and surrounding decor.
Loft in Lunenburg
4.96 out of 5 average rating, 645 reviews

‘The BOHO retreat’ (entire ‘loft’ suite)

A newly constructed loft apartment, nestled between Lunenburg and Mahone bay. Minutes from either. A beautiful open plan living space, high end bathroom, all rustically finished with reclaimed 200 yr old Douglas fir. A stunning private deck, to enjoy the beginning or end of your adventure around the south shore! Easy self check in, parking, and private. Please note- there is a kitchenette/coffee bar-no stove/oven to cook on. (Please see ‘amenities’ list, for full description).

Guest favourite
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, 104 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 favourite
A large historic home is set amidst lush greenery, featuring a double-storey façade with multiple windows and a charming front porch. Colorful flower baskets hang from the porch overhang, and a landscaped pathway leads to the entrance, enhancing the inviting exterior.
Apartment in Mahone Bay
4.97 out of 5 average rating, 103 reviews

Guest accomodation in Mahone Bay town

Beautiful guest unit 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.

Top Guest favourite
A modern single-story unit features large windows framed in black, complemented by red doors. Surrounding the unit, a gravel pathway leads to a decorative lighthouse structure. The outdoor area is equipped with wooden decking, providing a welcoming entry point to the seaside setting.
Bungalow in Lunenburg
4.98 out of 5 average rating, 169 reviews

Ocean front #14 BBQ HotTub Private Deck waterfront

HOOK'd 14 is your seaside sanctuary. Step into modern luxury in this open-concept unit, featuring a hot tub overlooking the sea 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 14 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Guest favourite
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
4.87 out of 5 average rating, 103 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!

Guest favourite
A spacious geo-dome is surrounded by lush trees, featuring large windows that provide a view of nature. An outdoor seating area is arranged on a patio, complemented by a fire pit and a barbecue, creating an inviting space for relaxation.
Dome in Hubbards
4.9 out of 5 average rating, 118 reviews

Mill Lake Retreat - Hydra Dome - Forested Retreat

• Newly built geo-dome • Treed property • Located in nature • Lake/dock access just across the street • 40 minutes to Halifax • Fire pit • BBQ • Large windows spanning one side of the dome • Skylight • Heat and AC • Open concept space • 1 queen bed • 1 double bed • 1 bathroom with stand-up shower • Fully equipped kitchen • Surrounded by wildlife • Multi-vehicle parking • Fast Wifi • Smart TV • Professionally cleaned • Professionally landscaped

Top Guest favourite
A comfortable living room is presented, featuring a neutral-colored sofa and armchair set adorned with colorful patterns. A coffee table sits in the center, surrounded by a textured area rug. Light enters through multiple windows, enhancing the space's inviting feel and a potted plant is placed nearby.
Guest suite in Lunenburg
4.96 out of 5 average rating, 367 reviews

A Suite Stay!

Whether you are looking for a weekend get away or have business in the local area, we have the perfect place for you. Just 3 minutes from Mahone Bay, 7 from Lunenburg and 25 minutes from Sensea Nordic Spa in Chester. Enjoy the convenience of a full kitchen, relaxing living room, spacious bedroom and bathroom! Enjoy an outdoor fire pit after a day of exploring! Meet our greeters, Max & Ruby. They love to see everyone!!

Top Guest favourite
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, 260 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, chocolate chips, syrup, rolled oats & oatmeal pkgs Studio Suite is an Apartment here in our main building, more detail ⬇ Find us on TT, IG & FB: covecottageecooasis

Popular amenities for Chester family-friendly rentals

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

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