
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$25,098 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
Indoor spacesKitchenQuiet

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.
KitchenIndoor spacesQuiet

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
Indoor spacesKitchenBathroom

Ocean Front #2 HotTub 2 bdrm Rooftopdeck BBQ 2bath
Escape to Oceanfront Bliss! This stunning property features an epic deck, perfect for sunbathing or evening gatherings. Step inside to discover modern finishes a blend style & comfort soak in a hot tub with ocean views. Rooftop deck for stargazing& Sunsets! The luxurious King Master suite with an ensuite and a cozy queen bedroom provide ample space for family and friends. Experience the ultimate lifestyle of relaxation, where every moment is a celebration, create memories. Book your stay now!
Indoor spacesFamilyGrill

OTW Close 2 Nordic Spa — Accepting Travel Nurses
• "Occupancy Fees or Property use tax" are local sales taxes charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins to NORDIC Spa • 10 mins from Mahone Bay & Oak Island • Free bikes with access to the Chester Connection Trail • BBQ, full kitchen and utensils, A/C, cable TV, wifi and parking • Open-concept living • Full bath on the main floor, 2 bedrooms on the second floor • The house is 100 years old so the stairs are steep • Porch has shared laundry facilities for the guesthouse next door
KitchenIndoor spacesLong stay

Captain's Quarters - 2 bedroom harbourview condo
Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Quarters is a bright and beautifully finished, spacious, 2-bedroom condo that is central to all that scenic Chester has to offer. Walking distance to the pubs, restaurants, bakery, yacht club & much more! Large, floor-to-ceiling windows offer a perfect view of Mahone Bay. Less than a 5-minute drive to Sensea Nordic Spa - a perfect home base for your South Shore stay.
Indoor spacesKitchenCleanliness

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!
FamilyKitchenDecor

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.
FamilyKitchenAccuracy

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.
KitchenFamilySleep quality

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.
Indoor spacesKitchenValue

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.
FamilyIndoor spacesComfort

Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, a private oceanfront home on Nova Scotia’s rugged coastline with wide Atlantic views, warm modern design, and space to gather with family and friends. The home includes a cedar sauna, outdoor hot tub, fire pit, BBQ, billiards table, and generous indoor and outdoor areas. It is ideal for guests looking for a quiet coastal escape, time together, and a comfortable place to relax after exploring Hubbards and the surrounding beaches.
FamilyIndoor spacesSleep quality
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Tiny Home Retreat w/ Hot Tub Near Chester
Indoor spacesKitchenAccuracy

Serene Cottage on 10 acres, Hot Tub, Lake Access
FamilyIndoor spacesWifi

The Narrows Nest
KitchenFamilySleep quality

Nova Glamping Log Cabin
KitchenFamilyAir conditioning

the Escape - A Private Oceanfront Getaway
Indoor spacesFamilyCheck-in

A Secluded Lakefront Spectacle
KitchenFamilyParking

Peaceful, private, forest hideaway for two
FamilyKitchenDecor

Lakefront Tiny Home w/ Hot Tub + Sunset Views
Indoor spacesFamilyQuiet
Family- and pet-friendly home rentals

Charming Historic Cottage on Main in Mahone Bay
FamilyIndoor spacesNearby

Little Pink Cottage
FamilyIndoor spacesValue

The Beach Barn + Cedar Sauna
Indoor spacesKitchenAmenities

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

Lovely Times Cottage - A Chester lakeside retreat
Indoor spacesFamilyValue

Unique oceanfront home near Lunenburg
KitchenFamilyCleanliness

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

Back Bay Cottage
FamilyIndoor spacesLayout
Family-friendly home rentals with a pool

Luxury Lakefront Suite - Hot Tub & Amenities!
FamilyIndoor spacesBathroom

Cozy Cottage on South Shore. 30 min from Halifax!
FamilyIndoor spacesHot tub

Beautiful new 6 bedroom lakehouse close to Halifax
KitchenIndoor spacesLayout

Lakefront Luxury Retreat
FamilyIndoor spacesAmenities

Oceanfront Cottage - Modern & Private
FamilyIndoor spacesView

Oceanside Home within the City; A Cycle Away!
Indoor spacesKitchenQuiet

North End Nest
FamilyIndoor spacesCheckout

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
Indoor spacesFamilyCondition
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$45,594 GYD | G$45,803 GYD | G$45,594 GYD | G$49,568 GYD | G$47,685 GYD | G$53,960 GYD | G$55,006 GYD | G$55,006 GYD | G$48,104 GYD | G$51,868 GYD | G$47,685 GYD | G$45,594 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
- Ellsworth Vacation rentals
- Dartmouth Vacation rentals
- Cape Breton Island Vacation rentals
- Gaspé Vacation rentals
- Lunenburg Vacation rentals
- Rissers Beach Provincial Park
- Oak Island
- Kejimkujik National Park & National Historic Site
- Hirtle's Beach
- Dalhousie University
- Lawrencetown Beach Provincial Park
- Halifax Citadel National Historic Site
- Conrad's Beach
- Big Mushamush Lake
- Long Lake Provincial Park
- Rainbow Haven Beach
- Shubie Park
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Halifax Public Gardens
- Luckett Vineyards
- Crystal Crescent Bch Provincial Pk
- Canadian Museum of Immigration at Pier 21
- Ski Martock
- Halifax Central Library
- Halifax Seaport Farmers' Market
- Scotiabank Centre
- Sir Sandford Fleming Park
- Museum of Natural History





