
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.

The Shore Shack
Shore Shack is a newly construction timber frame cabin on the Atlantic Ocean. Beautiful views and direct oceanfront. A Sandy beach within walking distance (at the end of Sand Beach road). The town of Liverpool is a five minute drive away. Very private! Whitepoint, Carter's and Summerville beach all a short drive away. A four person hot tub was added in March 2022. This property does not have an oven - does have 4 burner stove. Nova Scotia Tourist Registry RYA-2023-24-04142056359520676-77

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

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.

Guest accomodation in Mahone Bay town
Beautiful suite in quiet, central area of Mahone Bay. Steps to main street but away from the traffic and backing onto the park. The suite is one wing of a large, older historic home. The property is in the heart of one of the South Shore's most picturesque seaside towns. The property is about 1 hour from Halifax and the airport and is walkable to many restaurants, stores, the harbor, and trails. The children's park is steps away, as is the town swimming pool.

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.

Nova Glamping Log Cabin
Experience the natural beauty of Nova Scotia through your own island oasis experience! Our upscale, cozy log cabin is equipped with everything you need with a view you will never forget. Enjoy a unique blend of nature and luxury as you explore the island during the day and relax in your own private jacuzzi under the stars at night. We guarantee this experience will be one you’ll never forget and one that you’ll keep coming back to time and time again!

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.

Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, where minimalist Nordic design meets Nova Scotia’s rugged coastline. This oceanfront retreat offers panoramic views, a private cedar sauna, hot tub, and fire pit. Perfect for slowing down, soaking in the sea, watching the sunrise over the ocean, and reconnecting with loved ones. Every detail is designed to create balance, beauty, and intentional living.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

The Creation Lounge Retreat - A Unique Gem!

Middle Lake Retreat *with hot tub*

Hot Tub Retreat | Valley Views | Near Kentville AC

South Shore Sanctuary : Historic Church w/ Hot Tub

Green Goose Guesthouse on Tidal Lake, Queensland

Hot Tub & Sauna, Sleeps 8 – Private Waterfront!

Mill Lake Retreat - Lyra Dome with Private Hot Tub

Glamping Dome 2 StarGazer
Family- and pet-friendly home rentals

Witmere

Ocean front cottage, Mahone Bay

Waterfront cottage, private beach, LaHave River.

The Lookout - Cottage

Architecturally-designed: The Rosebay, B2 Lofts

The Beach Barn + Cedar Sauna

Welcome to the Cozy Quilt

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

Half Moon Cove Retreat

Oceanside Home within the City; A Cycle Away!

North End Nest

Home Away from Home - Entire Apartment

Beautiful new 6 bedroom lakehouse close to Halifax

Oceanfront Cottage - Modern & Private

Waterfront Apartment in Beautiful Fall River

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ562 | ﺩ.ﺇ551 | ﺩ.ﺇ529 | 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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- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Lawrencetown Beach Provincial Park
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Halifax Public Gardens
- Dalhousie University
- Halifax Central Library
- Maritime Museum of the Atlantic
- Halifax Waterfront Boardwalk
- Luckett Vineyards
- Crystal Crescent Bch Provincial Pk
- Kejimkujik National Park & National Historic Site
- Peggys Cove Lighthouse
- Long Lake Provincial Park
- Shubie Park
- Grand-Pré National Historic Site
- Museum of Natural History
- Scotiabank Centre
- Big Mushamush Lake





