
Family-friendly vacation rentals in Chester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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

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.

Charming Ocean Retreat
Perched on a hill overlooking the Aspotogan Cove, this lovingly restored 150-year-old family home offers everything you might need for a relaxing peaceful retreat. The backyard opens onto four acres of trails - perfect for mountain biking and hiking - and Bayswater Beach, one of the exquisite beaches on the South Shore, is only five minutes away. The beautifully appointed chef’s kitchen invites culinary play, and an extensive collection of games, books and movies will keep you well entertained.

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

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!

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

Private cottage on a lake - kayaks, SUP, fire pit
Private lakefront cottage tucked in the forest on a quiet, hidden lake. Swim, kayak & paddleboard from your own dock (no neighbors in sight). BBQ on the deck, spend long sunny days on the water, and end the night around the fire pit under the stars. Cozy inside with a movie projector, record player & murder mystery games. Pet-friendly. 1 hr to Halifax, 15 min to Bent Ridge Winery & Ontree Adventure Park. Follow @bluestonechalet to see why guests always need one more night.

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.

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.

Norse Geodesic Retreat (Freya)
Experience the epitome of relaxation and luxury at Norse Geodesic Retreat. Nestled amidst nature's embrace, our distinctive geodesic domes offer an unrivaled escape from the hustle and bustle of everyday life. Step into a world of elegance and tranquility as you gaze through floor-to-ceiling windows at the breathtaking views outside. Unwind on your private deck, where a rejuvenating soak in the hot tub awaits under the starlit sky.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

The Lazy Loon Lake House

The Shore Shack

Middle Lake Retreat *with hot tub*

South Shore Sanctuary : Historic Church w/ Hot Tub

Wilson's Coastal Club - C7

Green Goose Guesthouse on Tidal Lake, Queensland

Mill Lake Retreat - Lyra Dome with Private Hot Tub

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

Witmere

Tulip Suite - The Dordean Suites of Chester

The Lookout - Cottage

Spacious Lakefront Cottage Retreat

The Oaks Seaside Retreat

The Beach Barn + Cedar Sauna

Cozy log cabin nestled between Prospect & Shad Bay

Quarrie Cottage | Mahone Bay
Family-friendly home rentals with a pool

2-storey designer cottage - Shobac Farm Gate House

Half Moon Cove Retreat

All Decked Out in Mahone Bay

Oceanside Home within the City; A Cycle Away!

In ground HOT TUB + 2 primary bedrooms w/ ensuites

North End Nest

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 | ﺩ.ﺇ801 | ﺩ.ﺇ804 | ﺩ.ﺇ801 | ﺩ.ﺇ536 | ﺩ.ﺇ661 | ﺩ.ﺇ790 | ﺩ.ﺇ966 | ﺩ.ﺇ966 | ﺩ.ﺇ845 | ﺩ.ﺇ911 | ﺩ.ﺇ837 | ﺩ.ﺇ801 |
| 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 |
Quick stats about vacation rentals that are family-friendly in Chester

Total vacation rentals
Explore 30 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 1,100 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
30 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!
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- Rentals with a fireplace Chester
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- Pet-friendly rentals Chester
- Rentals with beach access Chester
- Rentals with a washer and dryer Chester
- Rentals with a patio Chester
- Cabin rentals Chester
- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Rissers Beach Provincial Park
- Oak Island
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Dalhousie University
- Halifax Waterfront Boardwalk
- Halifax Public Gardens
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Maritime Museum of the Atlantic
- Long Lake Provincial Park
- Halifax Central Library
- Shubie Park
- Big Mushamush Lake
- Luckett Vineyards
- Halifax Seaport Farmers' Market
- Kejimkujik National Park & National Historic Site
- Peggys Cove Lighthouse
- Ski Martock
- Grand-Pré National Historic Site
- Chester Golf Club





