
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 40 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $204 NZD per night before taxes and fees

Verified guest reviews
Over 1,110 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
40 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.

Luxury Tiny Home Retreat w/ Hot Tub Near Chester
A Modern Shipping Container Retreat Tucked away in Chester NS walking distance from nine mile lake, this sleek and stylish tiny home offers big comfort in a compact space. Featuring a cozy interior, outdoor seating, and all the essentials for a peaceful getaway. Unplug, unwind and experience container living like never before. ☆ Brand New Shipping Container 320 sqft tucked away in Chester NS. Nordic spa, Ski Martock, golf ☆ Hot tub ☆ Fully equipped Kitchen, Tea and coffee ☆ Wifi ☆ Large TV

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

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

Millet Lake House • Hot Tub • Sandy Beach
"Like having your own private resort" - Millet Lake House is welcoming, warm & every little comfort has been considered. Serious staycations start & end right here. Perfectly perched on peaceful forested acreage overlooking over 250ft of your own sandy beachfront, the setting is simply unmatched. Privacy, finishes, the outdoor toys & all of the special little touches to ensure everyone's vacation goals are exceeded. The reviews & the reputation as the South Shore's premium lake front retreat.

Luxury Lakefront Suite - Hot Tub & Amenities!
Executive Lakefront Retreat: Escape to our luxurious and private two bedroom (plus den) apartment above the garage, boasting exclusive amenities for a serene stay. Enjoy: Private Hot Tub & Outdoor Propane Fireplaces Swimming Pool & Full Outdoor Kitchen Water Activities: Kayak, paddle boat, fishing rods, and dock access Nearby Conveniences: Within 5 km, find Tim Hortons, supermarket, drug store, liquor store, gas station Convenient Location: Just a 20-minute drive to downtown Halifax.

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!

Spacious Lakefront Cottage Retreat
This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

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.

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.

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.

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

Peaceful, private, forest hideaway for two

Lakefront Tiny Home w/ Hot Tub + Sunset Views

Waterfront Honeymoon Loft

Nordic Tides Retreat Sauna & Spa

the Escape - A Private Oceanfront Getaway

Serene Cottage on 10 acres, Hot Tub, Lake Access

Glamping Dome 3 DriftWood

Nova Glamping Log Cabin
Family- and pet-friendly home rentals

Lovely Times Cottage - A Chester lakeside retreat

Little Pink Cottage

Koko Bay: Glamping, where glamour meets nature!

"Lisette's on Long Hill", cozy with boho charm

Private cabin on a lake - kayaks, SUP, fire pit

Back Bay Cottage

Charming Historic Cottage on Main in Mahone Bay

Ocean front cottage, Mahone Bay
Family-friendly home rentals with a pool

Cozy Cottage on South Shore. 30 min from Halifax!

Lakefront Luxury Retreat

Oceanfront Cottage - Modern & Private

Beautiful new 6 bedroom lakehouse close to Halifax

Oceanside Home within the City; A Cycle Away!

North End Nest

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA

Waterfront Apartment in Beautiful Fall River
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $371 NZD | $373 NZD | $371 NZD | $249 NZD | $306 NZD | $366 NZD | $448 NZD | $448 NZD | $391 NZD | $422 NZD | $388 NZD | $371 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
- Cape Breton Island Holiday rentals
- Dieppe Holiday rentals
- Gaspé Holiday rentals
- House rentals Chester
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Pet-friendly rentals Chester
- Rentals with a washing machine and dryer 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
- Rissers Beach Provincial Park
- Oak Island
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Lawrencetown Beach Provincial Park
- Kejimkujik National Park & National Historic Site
- Conrad's Beach
- Rainbow Haven Beach
- Long Lake Provincial Park
- Big Mushamush Lake
- Point Pleasant Park
- Shubie Park
- Maritime Museum of the Atlantic
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Ski Martock
- Halifax Seaport Farmers' Market
- Crystal Crescent Bch Provincial Pk
- Scotiabank Centre
- Museum of Natural History
- Sir Sandford Fleming Park
- Fisherman's Cove
- Bayswater Beach Provincial Park





