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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Top 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
4.98 out of 5 average rating, 431 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

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, 154 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
A charming, historic house is nestled on a hill, surrounded by vibrant flowers and greenery. The exterior showcases a blend of gray shingles and natural wood, with inviting porches that enhance its appeal. The sky above is bright with scattered clouds, adding to the home's radiant character.
Home in Hubbards
4.96 out of 5 average rating, 216 reviews

Charming Ocean Retreat

Perched on a hill overlooking the Aspotogan Cove, this lovingly restored 150-year-old family home offers everything you might need for a relaxing peaceful retreat. The backyard opens onto four acres of trails - perfect for mountain biking and hiking - and Bayswater Beach, one of the exquisite beaches on the South Shore, is only five minutes away. The beautifully appointed chef’s kitchen invites culinary play, and an extensive collection of games, books and movies will keep you well entertained.

Top guest favorite
Home in Lunenburg
4.96 out of 5 average rating, 140 reviews

Ocean Front #2 HotTub 2 bdrm Rooftopdeck BBQ 2bath

Escape to Oceanfront Bliss! This stunning property features an epic deck, perfect for sunbathing or evening gatherings. Step inside to discover modern finishes a blend style & comfort soak in a hot tub with ocean views. Rooftop deck for stargazing& Sunsets! The luxurious King Master suite with an ensuite and a cozy queen bedroom provide ample space for family and friends. Experience the ultimate lifestyle of relaxation, where every moment is a celebration, create memories. Book your stay now!

Superhost
A cozy living area features a comfortable sofa adorned with decorative pillows and a fur throw. A round wooden coffee table sits in front of a white electric fireplace, contributing warmth. The space showcases rustic wooden wall accents and light gray walls, enhancing a relaxed atmosphere.
Cabin in Martins Point
4.87 out of 5 average rating, 229 reviews

FFA Close to Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use taxes" is the mandatory local sales tax charged by Airbnb (HST 14%) • 3pm Checkin • 15 mins from NORDIC Spa • 10 mins from Mahone Bay • Shared laundry facilities • Free bikes provided with access to the Chester Connection Trail • A/C, cable TV, wifi & free parking on site • Cozy & comfortable with a large back deck, BBQ. Stand up shower only. • Please note this cottage has 7' ceilings (not 8') • The second bedroom is best suited for a child (more info below)

Guest favorite
A black-clad exterior is observed beside a spacious deck featuring two chairs. A vibrant sunset casts warm orange and pink hues across the sky, reflecting on the ocean waves below. The serene coastal view is complemented by the tranquility of the surrounding landscape.
Guest suite in Western Head
4.94 out of 5 average rating, 110 reviews

The Surf Shack

Cedar sauna just built! Surf Shack is down the hill from the Black Shack. It’s a loft style, open concept apartment with the bathroom on the first floor(access by outside staircase). With both an upper and lower deck, outside shower, fire pit and sauna! This is the perfect spot to get away and enjoy the incredible ocean views! 5km's from Liverpool and close to White Point, Summerville and Carter's beach. The perfect spot for a getaway! NS TOURIST REGISTRY #RYA-2023-24-04142047219327475-1118

Top guest favorite
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, 905 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 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, 283 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, go kayaking or swimming. We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

Top guest favorite
Two colorful adirondack chairs, one bright pink and one blue, are positioned on a wooden deck. A potted plant with vibrant flowers sits nearby, and a barbecue grill is visible in the background, enhancing the outdoor relaxation space.
Cottage in Chester
4.95 out of 5 average rating, 146 reviews

Moss Cottage on the Lake

Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.

Top guest favorite
A geodesic dome is nestled among lush greenery, with warm wooden accents visible on its exterior. The serene coastline and calm waters are in the background, while fluffy white clouds dot the blue sky, contributing to the peaceful island landscape.
Dome in West Dover
4.96 out of 5 average rating, 103 reviews

Nova Glamping Dover Dome

Experience the natural beauty of Nova Scotia through your own island oasis experience! Our upscale, cozy Geodesic Dome is equipped with everything you need with a view you will never forget. Enjoy a unique blend of nature and luxury as you explore the island during the day and relax in your own private jacuzzi under the stars at night. We guarantee this experience will be one you’ll never forget and one that you’ll keep coming back to time and time again!

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, 328 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.

Guest favorite
A sauna space features warm wooden walls and benches, creating a serene environment. Natural light filters in through a large window, illuminating a small basket of stones. The simplicity of the design emphasizes a calming retreat for relaxation.
Home in Hubbards
4.9 out of 5 average rating, 125 reviews

Nordic Tides Retreat Sauna & Spa

Welcome to Nordic Tides, where minimalist Nordic design meets Nova Scotia’s rugged coastline. This oceanfront retreat offers panoramic views, a private cedar sauna, hot tub, and fire pit. Perfect for slowing down, soaking in the sea, watching the sunrise over the ocean, and reconnecting with loved ones. Every detail is designed to create balance, beauty, and intentional living.

Popular amenities for Chester family-friendly rentals

When is the best time to visit Chester?

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Avg. priceﺩ.ﺇ 801ﺩ.ﺇ 804ﺩ.ﺇ 801ﺩ.ﺇ 536ﺩ.ﺇ 661ﺩ.ﺇ 790ﺩ.ﺇ 966ﺩ.ﺇ 966ﺩ.ﺇ 845ﺩ.ﺇ 911ﺩ.ﺇ 837ﺩ.ﺇ 801
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Quick stats about vacation rentals that are family-friendly in Chester

  • Total vacation rentals

    Explore 30 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 1,100 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

    30 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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