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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Top guest favourite
A cottage-style exterior displays a gray wood facade with white trim. A spacious deck features two white Adirondack chairs and a small table, surrounded by greenery. Red flowers in a planter add a pop of color, while a barbecue is placed in the corner.
Home in Mahone Bay
4.97 out of 5 average rating, 192 reviews

Mahone Bay Hide-Away

Hide-Away and rejuvenate in your very own 360 sq ft luxury tourist suite just a stones throw from the shops, galleries, dining, hiking and biking that picturesque Mahone Bay has to offer. This newly-built open concept tourist suite coupled with “ Getaway by the Bay” and “Haven In The Bay”, includes all the conveniences of home making this the ideal property to pamper yourself. The Hide-Away features luxury linens, gourmet equipped kitchen, spa-like ensuite, cable, Wi-Fi internet, dishwasher, washer/dryer, barbecue ( spring, summer, fall only) and fabulous indoor and outdoor space. Affiliated with Tourism NS, Canada Select and NS Approved. Snuggle and sip wine on the couch or enjoy your favourite local beer on the wraparound deck while firing a fine cut steak on the barbeque. It is up to you, it is your vacation. The Hide-Away on the Hill is the consummate location to use as your home base as you explore Nova Scotia. Book today and experience why our guests love to rebook. All our guests have access to the entire home and outdoor space. Your hosts, Pam and David, are born and raised in the area, live close by, available 24/7, and are an excellent resource to answer any questions you may have or suggest local excursions. Situated in the heart of Mahone Bay, this home is a great starting point to explore the southern shore and other parts of Nova Scotia. Peggy's Cove, Halifax, Annapolis Valley, Gulf tidal bore, surfing, and much more are all nearby. Mahone Bay is a small ocean side walkable community with local taxi service available. This home is a brand new construction in 2018. You can be one of the first to experience the luxury and detail designed for your comfort and enjoyment. Please view our other AIRBNB listing , Getaway By The Bay

Top 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, 399 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 serene lakefront view captures the luxury lake house surrounded by trees. The structure reflects gently in the calm water, showcasing warm tones from the setting sun. A private beach area with sand and a dock is visible, enhancing the tranquil atmosphere.
Cottage in Hubbards
4.98 out of 5 average rating, 255 reviews

Fox Point Lake House - Luxury Lakefront Rental!

Featured on Home Shores - Season 2, Episode 1! This one of a kind luxury lake house has plenty to offer. Gorgeous lakefront, private beach, hot tub that overlooks the lake, water views from the main floor and primary bedroom, wood fireplace and the list goes on. Other features include: - 30 mins from Halifax - Cathedral ceilings with A frame front - Built in wet bar with wine and beer fridge - Private sand beach - Salt water hot tub that comfortably sits 7 Check our IG - @foxpointlakehouse

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, 144 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 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 Apt at Cove Cottage Eco Oasis

Cove Cottage is a lakefront eco-retreat tucked into the woods, 45 mins from HRM. We vibe with nature. Walk the boardwalk, sit lakeside enjoying the views, feed the chickens, wander the gardens, or currently the snow banks ❄️ We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

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
4.78 out of 5 average rating, 116 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 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, 878 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, 175 reviews

Cozy Lakefront Cottage w/ wood stove near Martock

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, 111 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
The serene lake is bordered by trees and reflects a clear blue sky. A dock with two blue chairs extends into the water, and a floating device is visible nearby. The calm surface of the lake enhances the peaceful ambiance.
Home in Chester Basin
4.96 out of 5 average rating, 160 reviews

The Oasis on Blueberry Lane

Welcome to your private lakefront escape in Chester Grant. Swim from the dock on a warm, swimmable lake, paddle at sunrise, and soak in the hot tub beneath star-filled skies. Gather around indoor and outdoor wood fires in every season, then head inside for pool tournaments and spacious, comfortable living designed for connection and relaxation. Just 10 mins to Sensea Nordic Spa and 30 mins to Ski Martock, the perfect four-season retreat for families and friends year-round.

Top guest favourite
Bungalow in Lunenburg
4.99 out of 5 average rating, 228 reviews

Ocean front HotTub Private Deck waterfront BBQ

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.

Superhost
A geodesic dome is positioned on a wooden deck, surrounded by gravel landscaping and natural stone accents. Sturdy steps lead up to the dome entrance, while tall trees are visible in the background, contributing to the serene, forested setting.
Dome in Chester
4.89 out of 5 average rating, 318 reviews

Norse Geodesic Retreat (Freya)

Experience the epitome of relaxation and luxury at Norse Geodesic Retreat. Nestled amidst nature's embrace, our distinctive geodesic domes offer an unrivaled escape from the hustle and bustle of everyday life. Step into a world of elegance and tranquility as you gaze through floor-to-ceiling windows at the breathtaking views outside. Unwind on your private deck, where a rejuvenating soak in the hot tub awaits under the starlit sky.

Popular amenities for Chester family-friendly rentals

When is the best time to visit Chester?

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Avg. price$195 SGD$192 SGD$184 SGD$186 SGD$230 SGD$275 SGD$336 SGD$336 SGD$294 SGD$317 SGD$291 SGD$278 SGD
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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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,230 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chester holiday rentals include wifi 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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