
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.

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

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

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath
- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

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.

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.

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

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!

'Breeze from LaHave'-Cozy&Modern Walkout Basement
* COVID-19 quarantine not accepted. * 'Breeze from LaHave' is a bright & cozy walkout basement suit, entirely used for guests. It is located at the hub of scenic South Shore, reaching major tour destinations within 20 minutes, such as Lunenburg, Mahone Bay, enjoying the convenient amenities & services of hub town such as Hospital, mall, cafes, restaurants and banks, all within 5min walking. If you like walking in woods, Centennial Trail is directly connected to our Airbnb backyard.

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.

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, syrup, rolled oats & oatmeal pkgs & of course coffee and tea. We are scent free and all natural with 100% cotton bedding! Studio Suite is an Apartment here in our main building, more detail ⬇ Find us on TT, IG & FB: covecottageecooasis

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!

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

The Beach Loft: 5-bedroom

“Fox Hollow Retreat I” - Cozy, Quite and Clean

Hot Tub 2 Bed House NEW Kentville A/C Valley Views

The Paddling Dome - Lakefront - Hot Tub - Sauna

Fox Point Lake House - Luxury Lakefront Rental!

Luke's Lodge with hot tub & private lake access

Glamping Dome 3 DriftWood

South Shore cottage with ocean views
Family- and pet-friendly home rentals

Ocean front cottage, Mahone Bay

Pet-Friendly Glamping Dome close to Peggy’s Cove!

Boat House

Unique oceanfront home near Lunenburg

Merganser Guest Suite

Cottage on Main St. Mahone Bay

Welcome to the Cozy Quilt

Cozy log cabin nestled between Prospect & Shad Bay
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
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $213 CAD | $209 CAD | $201 CAD | $204 CAD | $251 CAD | $300 CAD | $367 CAD | $367 CAD | $321 CAD | $304 CAD | $248 CAD | $244 CAD |
| Avg. temp | -6 °C | -6 °C | -2 °C | 4 °C | 10 °C | 14 °C | 17 °C | 17 °C | 14 °C | 9 °C | 4 °C | -2 °C |
Quick stats about vacation rentals that are family-friendly in Chester

Total vacation rentals
Explore 40 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 1,150 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

Wifi availability
40 of Chester vacation 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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- Family-friendly rentals Nova Scotia
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- Cresent Beach
- Rissers Beach Provincial Park
- Crescent Beach, Lunenburg County, Nova Scotia
- Hirtle's Beach
- Atlantic Splash Adventure
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Beach Meadows Beach
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- Halifax Central Library




