
Family-friendly holiday rentals in Chester
Find and book unique family-friendly homes on Airbnb
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 $105 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!
Top-rated family-friendly rentals in Chester
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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

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.

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.

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

The Oasis on Blueberry Lane
Welcome to your private lakefront escape in Chester Grant. Swim from the dock on a warm, swimmable lake, paddle at sunrise, and soak in the hot tub beneath star-filled skies. Gather around indoor and outdoor wood fires in every season, then head inside for pool tournaments and spacious, comfortable living designed for connection and relaxation. Just 10 mins to Sensea Nordic Spa and 30 mins to Ski Martock, the perfect four-season retreat for families and friends year-round.

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.

Waterfront loft with million dollar view- Suite 2
These unique and thoughtful suites, each of the three units are outfitted with subtle nuances giving the spaces their own special feel. Visitors will enjoy designer micro-kitchens, fully stocked with amenities any food enthusiast would appreciate. A cozy wood stove for those chillier evenings. All units have a special secondary sleeping nest area accessible by ladder. A serene place to hide away and watch for shooting stars through the skylight windows.

Lakeview Cottage | Fox Point Lake | Hot tub/Kayaks
Welcome to our charming Lakeview cottage on Fox Point Lake in Hubbards, NS! This rustic log home boasts 3 bedrooms and 1.5 baths, making it perfect for families or friends seeking a peaceful retreat. Enjoy our private dock on the lake and take advantage of kayaks for fun-filled water adventures (seasonal). Unwind, reconnect with nature, and create cherished memories. Book now for an unforgettable lakeside getaway!

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.

OceanFront #12 HotTub Private Deck waterfront BBQ
Take it easy at this unique and tranquil getaway.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 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

The Lazy Loon Lake House

Serene Cottage on 10 acres, Hot Tub, Lake Access

Nova Glamping Log Cabin

Wilson's Coastal Club - C7

Seafarers Hideaway

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed

Peaceful, private, forest hideaway for two

Mill Lake Retreat - Lyra Dome with Private Hot Tub
Family- and pet-friendly home rentals

The Whale House

Spacious Lakefront Cottage Retreat

White Cottage

Captain's Quarters - 2 bedroom harbourview condo

The Beach Barn + Cedar Sauna

Back Bay A-Frame

Sunny Sanctuary in Martin's River

Koko Bay: Glamping, where glamour meets nature!
Family-friendly home rentals with a pool

Half Moon Cove Retreat

Oceanside Home within the City; A Cycle Away!

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

Relaxing Oceanfront Retreat- private luxury

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 | $380 NZD | $382 NZD | $380 NZD | $254 NZD | $314 NZD | $375 NZD | $458 NZD | $458 NZD | $401 NZD | $432 NZD | $397 NZD | $380 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 |
Destinations to explore
- Halifax Holiday rentals
- Bar Harbor Holiday rentals
- Moncton Holiday rentals
- Charlottetown Holiday rentals
- Fredericton Holiday rentals
- Saint John Holiday rentals
- Bangor Holiday rentals
- Dartmouth Holiday rentals
- Ellsworth Holiday rentals
- Lunenburg Holiday rentals
- Dieppe Holiday rentals
- Southwest Harbor Holiday rentals
- House rentals Chester
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Rentals with a washing machine and dryer Chester
- Pet-friendly rentals Chester
- Rentals with beach access Chester
- Rentals with a fireplace Chester
- Rentals with a patio Chester
- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Dalhousie University
- Kejimkujik National Park & National Historic Site
- Lawrencetown Beach Provincial Park
- Rainbow Haven Beach
- Conrad's Beach
- Halifax Waterfront Boardwalk
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Shubie Park
- Long Lake Provincial Park
- Canadian Museum of Immigration at Pier 21
- Big Mushamush Lake
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Halifax Seaport Farmers' Market
- Peggys Cove Lighthouse
- Ski Martock
- Grand-Pré National Historic Site
- Crystal Crescent Bch Provincial Pk





