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

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, 204 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.

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

4.9 out of 5 average rating, 213 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 15%) • 3pm Checkin • 15 mins from NORDIC Spa • 10 mins from Mahone Bay • 3 mins from Oak Island • 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 it is a cottage with 7' ceilings (not 8') • The second bedroom is best suited for a child (more info below)

Guest favorite

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, 168 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)

Top guest favorite

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, 234 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 favorite

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, 629 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 favorite

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, 100 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 favorite

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, 154 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.

Top guest favorite

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, 362 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 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

4.95 out of 5 average rating, 253 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

Top guest favorite

A spacious living area features a large triangular window wall offering panoramic views of the ocean and surrounding trees. A comfortable couch and a rustic wooden coffee table are positioned near a cozy wood stove. A window seat, adorned with soft pillows and a throw, invites relaxation.

Cottage in Deep Cove

4.99 out of 5 average rating, 111 reviews

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a canopy of starry skies. Overlooking the entrance to Deep Cove, and out towards Chester, Nova Scotia, this secluded four-season cottage offers an idyllic escape, ideal for a romantic couple's getaway or a tranquil retreat from the everyday.

Guest favorite

A tranquil lakeside setting is depicted at sunset, showcasing vibrant colors reflecting off the calm water. A wooden bench sits nearby, framed by trees. A small dock extends onto the lake, adding to the serene atmosphere of the natural surroundings.

Guesthouse in Chester Basin

4.86 out of 5 average rating, 139 reviews

Hutt Lake Studio 10 minutes away from Sensea Spa

Relax and unwind at this unique and tranquil getaway. Air conditioned for your comfort. Steps away from a lake for you with private beach to enjoy. Kayaks and pedalboat for you free to use at your own risk. Central location with Mahone Bay, Lunenburg, Peggy’s Cove and Halifax all a very easy drive from your cottage. Very quiet and peaceful location.

Guest favorite

A geodesic dome is situated among lush greenery and rock formations, with a wooden deck connecting it to the natural landscape. Surrounding trees provide a sense of seclusion, while a clear blue sky complements the serene environment.

Dome in Chester

4.92 out of 5 average rating, 284 reviews

Norse Geodesic Retreat (Balder)

Discover a summer sanctuary in our geodesic domes, where serenity meets adventure. Savor complimentary wine on your private deck amidst verdant surroundings. Dive into your private hot tub oasis or embark on a kayaking adventure on the nearby lake. Experience the perfect blend of relaxation and excitement amid nature's embrace.