
Family-friendly holiday 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.

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

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)

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

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

‘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).

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.

Guest accomodation in Mahone Bay town
Beautiful guest unit 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.

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.

Pleasant Street Suite
Location, location, location! This studio apartment is located in the heart of Mahone Bay. Restaurants, shops, grocery store, pharmacy, and of course the three churches are within a 5 minute walk. The space is colourful and cheery with an east coast vibe. The apartment has a well equipped kitchenette if you prefer to cook light meals yourself. There is also a dining area which could be used as a very comfortable work space. Enjoy our beautiful town!

Mill Lake Retreat - Hydra Dome - Forested Retreat
• Newly built geo-dome • Treed property • Located in nature • Lake/dock access just across the street • 40 minutes to Halifax • Fire pit • BBQ • Large windows spanning one side of the dome • Skylight • Heat and AC • Open concept space • 1 queen bed • 1 double bed • 1 bathroom with stand-up shower • Fully equipped kitchen • Surrounded by wildlife • Multi-vehicle parking • Fast Wifi • Smart TV • Professionally cleaned • Professionally landscaped

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!!

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
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Wilson's Coastal Club - C5

The Fishing Dome - Lakefront - Hot Tub - Sauna

Lakefront home with hot tub

Fox Point Lake House - Luxury Lakefront Rental!

Stunning, secluded chalet with wood fired hot tub

Glamping Dome 2 StarGazer

Falls Lake Burrow - 2 bdrm Cottage w/hot tub

Orig.Inns - Cozy Bunkie Hideaway with Hot Tub
Family- and pet-friendly home rentals

Waterfront cottage, private beach, LaHave River.

The Beach Loft: 5-bedroom

the ISLAND - A Charming Island Cottage and Bunkie

Merganser Guest Suite

Welcome to the Cozy Quilt

Cozy log cabin nestled between Prospect & Shad Bay

The Harmony Grand at Molega Lake

Back Bay Cottage
Family-friendly home rentals with a pool

2-storey designer cottage - Shobac Farm Gate House

Oceanside Home within the City; A Cycle Away!

In ground HOT TUB + 2 primary bedrooms w/ ensuites

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

Oceanfront Cottage - Modern & Private

Waterfront Apartment in Beautiful Fall River

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
Quick stats about holiday rentals that are family-friendly in Chester
Total rentals
40 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
1.2K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
Destinations to explore
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- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Cresent Beach
- Rissers Beach Provincial Park
- Crescent Beach, Lunenburg County, Nova Scotia
- Atlantic Splash Adventure
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Beach Meadows Beach
- Bayswater Beach Provincial Park
- Chester Golf Club
- Conrad's Beach
- Cape Bay Beach
- Splashifax
- Lawrencetown Beach
- Canadian Museum of Immigration at Pier 21
- Hunts Point Beach
- The Links at Brunello
- Lawrencetown Beach Provincial Park
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Little Rissers Beach
- Oxners Beach
- Halifax Central Library