Photo by Julie Miller

Chestertown family rentals

We found 306 family rentals — enter your dates for availability

Where to?

Dates

November 2025

December 2025

Find the best place to stay - Chestertown

Showing deals for: 6 Feb - 9 Feb

Premier Host

Sleeps 6 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 apartment

AU$537 per night

includes taxes & fees

Sleeps 10 · 5 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$1,211 per night

includes taxes & fees

Premier Host

Sleeps 5 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

AU$349 per night

includes taxes & fees

Sleeps 10 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$903 per night

includes taxes & fees

House

Condo/Apartment

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value