
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

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.

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)

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!

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

Forested Cozy Cabin with Garden Area in Halifax
Welcome to our tranquil getaway; a warm place to unwind during your travels. Just 10 minutes from downtown Halifax, we are located on the edge of a forest and surrounded by terraced gardens, you will feel immersed in nature. Catch a sunrise over the Halifax harbour, enjoy conversation around the outdoor fire pit, and barbeque on the deck. We are friendly hosts, glad to answer questions or assist with your stay to make you more comfortable or help you with your travels.

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed
Nate’s Nest is super close to the Historic town of Lunenburg Huge deck outdoor living Hot tub, Sun Sets Waterfront Ocean views quite charming unit with 2 baths modern kitchen & Den for friends to visit. HOOKd home Nestled in a very rare community lil HOOK Properties inclusive of a private pier boat launch and like minded people who enjoy living on the water A water lovers dream Wake up to sparkly water shimmering into your windows or enjoy star gazing in the hot tub.

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.

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!

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.

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.

Cozy Oceanfront Escape 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.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Wilson's Coastal Club - C4

The Lazy Loon Lake House

Serene Cottage on 10 acres, Hot Tub, Lake Access

South Shore Sanctuary : Historic Church w/ Hot Tub

Scenic Lakefront Suite with Private Jacuzzi

Green Goose Guesthouse on Tidal Lake, Queensland

Fox Point Lake House - Luxury Lakefront Rental!

Luke's Lodge with hot tub & private lake access
Family- and pet-friendly home rentals

Tulip Suite - The Dordean Suites of Chester

The Whale House

Architecturally-designed: The Rosebay, B2 Lofts

Spacious Lakefront Cottage Retreat

Cozy log cabin nestled between Prospect & Shad Bay

The Bear’s Den treehouse lodging.

Quarrie Cottage | Mahone Bay

The Harmony Grand at Molega Lake
Family-friendly home rentals with a pool

Half Moon Cove Retreat

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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $368 NZD | $370 NZD | $368 NZD | $247 NZD | $304 NZD | $363 NZD | $444 NZD | $444 NZD | $388 NZD | $419 NZD | $385 NZD | $368 NZD |
| 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 holiday rentals that are family-friendly in Chester

Total holiday rentals
Explore 30 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $101 NZD per night before taxes and fees

Verified guest reviews
Over 1,100 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chester holiday 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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- Family-friendly rentals Nova Scotia
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- Rissers Beach Provincial Park
- Oak Island
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Dalhousie University
- Halifax Waterfront Boardwalk
- Point Pleasant Park
- Halifax Public Gardens
- Canadian Museum of Immigration at Pier 21
- Long Lake Provincial Park
- Maritime Museum of the Atlantic
- Shubie Park
- Halifax Central Library
- Big Mushamush Lake
- Luckett Vineyards
- Kejimkujik National Park & National Historic Site
- Ski Martock
- Halifax Seaport Farmers' Market
- Grand-Pré National Historic Site
- Peggys Cove Lighthouse
- Museum of Natural History





