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
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, 260 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 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, 150 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

Guest favorite
Home in Chester Basin
4.93 out of 5 average rating, 198 reviews

Millet Lake House • Hot Tub • Sandy Beach

"Like having your own private resort" - Millet Lake House is welcoming, warm & every little comfort has been considered. Serious staycations start & end right here. Perfectly perched on peaceful forested acreage overlooking over 250ft of your own sandy beachfront, the setting is simply unmatched. Privacy, finishes, the outdoor toys & all of the special little touches to ensure everyone's vacation goals are exceeded. The reviews & the reputation as the South Shore's premium lake front retreat.

Guest favorite
A newly constructed timber frame cabin is situated near the Atlantic Ocean, surrounded by dense greenery. The shoreline and rocky coast are visible in the background, while the ocean glistens under sunlight. The cabin features a simple porch and expansive outdoor space.
Cottage in Western Head
4.96 out of 5 average rating, 221 reviews

The Shore Shack

Shore Shack is a newly construction timber frame cabin on the Atlantic Ocean. Beautiful views and direct oceanfront. A Sandy beach within walking distance (at the end of Sand Beach road). The town of Liverpool is a five minute drive away. Very private! Whitepoint, Carter's and Summerville beach all a short drive away. A four person hot tub was added in March 2022. This property does not have an oven - does have 4 burner stove. Nova Scotia Tourist Registry RYA-2023-24-04142056359520676-77

Superhost
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
4.94 out of 5 average rating, 215 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 favorite
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, 179 reviews

Spacious Lakefront Cottage Retreat

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 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, 106 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.

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 dining area is showcased with a wooden table surrounded by six metal chairs. Natural light filters in through a large window, highlighting the beam ceiling and stone accents. A decorative bowl rests at the center of the table, complemented by a plant and surfboards nearby.
Cottage in Queensland
4.98 out of 5 average rating, 129 reviews

The Beach Loft: 5-bedroom

This pretty beach house is located just steps from the beautiful Seawall beach. Relax in the hot tub, hammock or next to the fire. The perfect getaway that is only 34min from Halifax. Featuring a wood burning fireplace and stone accents. Private hot tub overlooking the ocean. Post and beam Construction. Ocean views. Seawall beach is between Queensland and Cleveland’s beach. Also located on Rails to Trails path. Minutes to restaurants and coffee shops in Hubbards.

Guest favorite
An upscale log cabin sits on a rocky landscape, surrounded by grass and trees, overlooking serene waters. A fire pit with seating is positioned in front, while a private hot tub is nearby, offering a perfect spot to enjoy the natural beauty of the island.
Island in West Dover
4.95 out of 5 average rating, 125 reviews

Nova Glamping Log Cabin

Experience the natural beauty of Nova Scotia through your own island oasis experience! Our upscale, cozy log cabin 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!

Top guest favorite
Home in Lunenburg
5 out of 5 average rating, 159 reviews

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath

Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

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, 117 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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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.ﺇ220 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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