
Family-friendly vacation rentals in Chester
Find and book unique family-friendly homes on Airbnb
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 G$25,094 GYD per night before taxes and fees

Verified guest reviews
Over 1,110 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

Wi-Fi availability
40 of Chester vacation 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.

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
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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
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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.
FamilyIndoor spacesHot tub

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!
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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.
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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
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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.
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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.
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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.
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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.
Indoor spacesFamilyNearby

Waterfront Retreat
If you are looking for a peaceful, country retreat on the water, you've found it! Welcome to our beautiful house on the Atlantic Ocean, only a 20 minute drive from the gorgeous, colourful towns of Chester and Hubbards, and approximately an hour away from Mahone Bay, the well-known town of Lunenburg, and the city of Halifax. The South Shore of Nova Scotia boasts plenty of shopping, restaurants, and summer activities that interact with the breathtaking scenery.
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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.
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Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Nordic Tides Retreat Sauna & Spa
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Serene Cottage on 10 acres, Hot Tub, Lake Access
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Nova Glamping Log Cabin
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Fox Point Lake House - Luxury Lakefront Rental!
KitchenIndoor spacesView

Blysteiner Lake Dome
KitchenFamilyLayout

Peaceful, private, forest hideaway for two
Indoor spacesFamilyHot tub

Waterfront Honeymoon Loft
Indoor spacesFamilyCondition

Glamping Dome 3 DriftWood
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Family- and pet-friendly home rentals

Ocean front cottage, Mahone Bay
FamilyKitchenCondition

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

Mallard on Church Lake Accessible Lakefront AFrame
Indoor spacesFamilyDecor

the ISLAND - A Charming Island Cottage and Bunkie
Indoor spacesFamilySleep quality

Unique oceanfront home near Lunenburg
FamilyKitchenWalkability

The Beach Barn + Cedar Sauna
Indoor spacesFamilyBeach

Lakefront home with hot tub
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Back Bay Cottage
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Family-friendly home rentals with a pool

Lakefront Luxury Retreat
Indoor spacesFamilyPets

Half Moon Cove Retreat
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Oceanside Home within the City; A Cycle Away!
FamilyIndoor spacesComfort

In ground HOT TUB + 2 primary bedrooms w/ ensuites
Indoor spacesKitchenLong stay

North End Nest
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Oceanview Luxury Estate - Magazine Perfect!
Indoor spacesFamilyView

Beautiful new 6 bedroom lakehouse close to Halifax
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Oceanfront Cottage - Modern & Private
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When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$45,587 GYD | G$45,796 GYD | G$45,587 GYD | G$49,560 GYD | G$47,678 GYD | G$53,952 GYD | G$54,997 GYD | G$54,997 GYD | G$48,096 GYD | G$51,860 GYD | G$47,678 GYD | G$45,587 GYD |
| 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 Vacation rentals
- Bar Harbor Vacation rentals
- Moncton Vacation rentals
- Charlottetown Vacation rentals
- Fredericton Vacation rentals
- Saint John Vacation rentals
- Bangor Vacation rentals
- Dartmouth Vacation rentals
- Ellsworth Vacation rentals
- Cape Breton Island Vacation rentals
- Gaspé Vacation rentals
- Lunenburg Vacation rentals
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Kejimkujik National Park & National Historic Site
- Lawrencetown Beach Provincial Park
- Halifax Citadel National Historic Site
- Conrad's Beach
- Rainbow Haven Beach
- Big Mushamush Lake
- Long Lake Provincial Park
- Shubie Park
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Crystal Crescent Bch Provincial Pk
- Ski Martock
- Halifax Seaport Farmers' Market
- Scotiabank Centre
- Sir Sandford Fleming Park
- Museum of Natural History
- Fisherman's Cove
- Bayswater Beach Provincial Park





