
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$25,091 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.

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.
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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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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 or gardens, sit lakeside enjoying the views, feed the chickens. Sep28-Oct1 - deeply discounted for construction noise 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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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!
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Kaikoura Cottage - In the Heart of Mahone Bay
Kaikoura Cottage in the heart of the iconic town of Mahone Bay is a newly (2021) renovated 2 bedroom, 2.5 bath tastefully appointed cottage a short stroll to the picturesque waterfront or the popular multi use rails to trails. This peaceful space is at the epicenter of so many potential adventures. Kayak along the coast, visit the beach, stroll the historic town of Lunenburg, bike the trail, enjoy the local brew pub, relax at Chester's Sensea Nordic Spa. It's all yours to savour and enjoy.
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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
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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.
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Lakefront Cottage near Chester | BBQ + Lake Access
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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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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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.
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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.
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Endeavour Cottage
Take it easy at this unique and tranquil getaway. Enjoy your stay in our private lakefront cottage that’s only a short walking distance to the heart of Chester to explore local shops and restaurants. The Nordic Spa, Golf Club, Yacht Club and Beach are only minutes away. We are nestled in a hidden peaceful yet central location making our cottage the perfect getaway for all!
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Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Waterfront loft with million dollar views- Suite 1
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Fox Point Lake House - Luxury Lakefront Rental!
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Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed
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The Narrows Nest
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Oceanfront | Hot Tubs | Sauna | Gym | Game Rooms
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Serene Cottage on 10 acres, Hot Tub, Lake Access
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The Creation Lounge Retreat - A Unique Gem!
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Peaceful, private, forest hideaway for two
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Family- and pet-friendly home rentals

"Lisette's on Long Hill", cozy with boho charm
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Charming Historic Cottage on Main in Mahone Bay
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Unique oceanfront home near Lunenburg
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Lovely Times Cottage - A Chester lakeside retreat
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The Beach Barn + Cedar Sauna
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Back Bay Cottage
Indoor spacesFamilyHeating

Pet-Friendly Glamping Dome close to Peggy’s Cove!
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Private cabin on a lake - kayaks, SUP, fire pit
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Family-friendly home rentals with a pool

Luxury Lakefront Suite - Hot Tub & Amenities!
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Cozy Cottage on South Shore. 30 min from Halifax!
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Lakefront Luxury Retreat
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Beautiful new 6 bedroom lakehouse close to Halifax
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Seacliff - Luxury Waterfront Paradise - Pool & Spa
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North End Nest
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Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
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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$45,582 GYD | G$45,791 GYD | G$45,582 GYD | G$49,555 GYD | G$47,673 GYD | G$53,946 GYD | G$54,992 GYD | G$54,992 GYD | G$48,091 GYD | G$51,855 GYD | G$47,673 GYD | G$45,582 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
- Dieppe Vacation rentals
- Rissers Beach Provincial Park
- Oak Island
- Kejimkujik National Park & National Historic Site
- Hirtle's Beach
- Lawrencetown Beach Provincial Park
- Dalhousie University
- Halifax Citadel National Historic Site
- Conrad's Beach
- Big Mushamush Lake
- Long Lake Provincial Park
- Shubie Park
- Rainbow Haven Beach
- 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
- Fisherman's Cove
- Sir Sandford Fleming Park
- Queensland Beach Provincial Park





