
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$25,104 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

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 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

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!

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.

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.

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.

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

Birchwood on the Lake (with Hot Tub)

Wilson's Coastal Club - C5

Serene Cottage on 10 acres, Hot Tub, Lake Access

Nova Glamping Log Cabin

Lakefront home with hot tub

Fox Point Lake House - Luxury Lakefront Rental!

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

Peaceful, private, forest hideaway for two
Family- and pet-friendly home rentals

Ocean front cottage, Mahone Bay

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

Mallard on Church Lake Accessible Lakefront AFrame

Captain's Quarters - 2 bedroom harbourview condo

Charming Historic Cottage on Main in Mahone Bay

The Bear’s Den treehouse lodging.

Sunny Sanctuary in Martin's River

Back Bay Cottage
Family-friendly home rentals with a pool

Lakefront Luxury Retreat

Half Moon Cove Retreat

Oceanside Home within the City; A Cycle Away!

In ground HOT TUB + 2 primary bedrooms w/ ensuites

North End Nest

Oceanview Luxury Estate - Magazine Perfect!

Beautiful new 6 bedroom lakehouse close to Halifax

Oceanfront Cottage - Modern & Private
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$45,606 GYD | G$45,815 GYD | G$45,606 GYD | G$30,543 GYD | G$37,656 GYD | G$44,978 GYD | G$55,020 GYD | G$55,020 GYD | G$48,116 GYD | G$51,882 GYD | G$47,698 GYD | G$45,606 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
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- House rentals Chester
- Rentals with beach access Chester
- Rentals with a washer and dryer Chester
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Rentals with a fireplace Chester
- Rentals with a patio Chester
- Pet-friendly rentals Chester
- Cabin rentals Chester
- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Dalhousie University
- Halifax Citadel National Historic Site
- Kejimkujik National Park & National Historic Site
- Lawrencetown Beach Provincial Park
- Halifax Waterfront Boardwalk
- Conrad's Beach
- Rainbow Haven Beach
- Long Lake Provincial Park
- Maritime Museum of the Atlantic
- Point Pleasant Park
- Shubie Park
- Big Mushamush Lake
- Halifax Public Gardens
- Canadian Museum of Immigration at Pier 21
- Luckett Vineyards
- Grand-Pré National Historic Site
- Peggys Cove Lighthouse
- Halifax Central Library
- Ski Martock
- Halifax Seaport Farmers' Market
- Crystal Crescent Bch Provincial Pk





