Family-friendly holiday rentals in Chester

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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 favourite
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, 389 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 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
4.94 out of 5 average rating, 142 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
Bungalow in Lunenburg
4.99 out of 5 average rating, 153 reviews

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath

- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

Top Guest favourite
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, 211 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 favourite
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
4.77 out of 5 average rating, 109 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 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, 244 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
The cabin's exterior is framed by trees, illuminated by warm interior lights that reflect off large windows. A spacious wooden deck is visible, featuring two red chairs positioned towards the inviting entrance. The structure showcases a triangular gabled roof and a charming mix of wood siding.
Cabin in LaHave
4.97 out of 5 average rating, 871 reviews

East Coast charm, cabin and hot tub by the river

The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. Come for a magical getaway. Tucked away in the woods along side a babbling brook. Enjoy morning coffee on the deck, BBQ your dinner overlooking the river, groove to our vintage record collection, keep toasty by the wood stove and float in the hot tub under the stars. This is a wonderful cabin experience you won't forget!

Top Guest favourite
A welcoming porch is adorned with two light blue adirondack chairs, positioned to overlook a serene lake. The ground is covered in vibrant autumn leaves, and trees in the background are reflected in the calm water. The scene captures a peaceful outdoor retreat.
Cottage in Chester
4.96 out of 5 average rating, 173 reviews

Large Pet Friendly Lakefront cottage in Chester

This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

Top 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, 109 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 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, 275 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

Guest favourite
Home in Mahone Bay
4.97 out of 5 average rating, 218 reviews

Mahone Bay Ocean Retreat

Your luxury ocean getaway and private spa for two. Private beach access, keyless self check-in. On the beautiful South Shore minutes from town. Cathedral ceilings & epic views. Four seasons. Hot-tub, full spectrum infrared sauna, both indoor & outdoor rainfall showers. Indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, Netflix, and King size bed with premium linens. A calm, luxurious space flooded with natural light.

Top Guest favourite
A wooden deck extends from the cottage, featuring a covered seating area and several adirondack chairs. The cottage's exterior is a combination of wood and black panels, framed by lush greenery. A grill is placed under the shelter, ready for outdoor cooking.
Cottage in Lunenburg
4.98 out of 5 average rating, 121 reviews

A Secluded Lakefront Spectacle

Kick back and relax in this calm, stylish space. This lake side cottage is located minutes from the historic towns of Lunenburg and Mahone Bay. Regardless of which direction you go, there is an abundance of choices. Whether you enjoy outdoor activities such as beaches, hiking, off road and water sports, or would rather site see and dine out, this area offers it all. If relaxing while overlooking the lake is what you would prefer then this is the perfect setting.

Popular amenities for Chester family-friendly rentals

When is the best time to visit Chester?

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Avg. price$224 AUD$219 AUD$211 AUD$213 AUD$263 AUD$314 AUD$385 AUD$385 AUD$336 AUD$319 AUD$260 AUD$256 AUD
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Quick stats about holiday rentals that are family-friendly in Chester

  • Total holiday rentals

    Explore 40 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $73 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,230 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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