Aerial panorama of Kent Narrows earliest English settlement in Maryland, entrance to popular tourist spot Kent Island, marina, sail boats Queen Anne's County, fishing village on the Chesapeake

Kent County family rentals

We found 293 family rentals — enter your dates for availability

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December 2025

January 2026

Find the best place to stay - Kent County

Showing deals for: 6 Mar - 9 Mar

Life is better at the RIVER!--Cozy waterfront cottage

Sleeps 5 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

NZ$441 per night

includes taxes & fees

Premier Host

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Sleeps 8 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 home

NZ$938 per night

includes taxes & fees

Premier Host

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Sleeps 10 · 4 bedrooms · 2+ bathrooms

for 3 nights, 1 home

NZ$1,125 per night

includes taxes & fees

Premier Host

Historic Manor House on Beautiful Eastern Shore Estate

Sleeps 13 · 6 bedrooms · 4+ bathrooms

for 3 nights, 1 home

NZ$2,748 per night

includes taxes & fees

Premier Host

First Floor Studio Apartment in Historic Chestertown

Sleeps 3 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

NZ$278 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Kent County

Life is better at the RIVER!--Cozy waterfront cottage

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Blissful Retreat In Rock Hall

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Historic Manor House on Beautiful Eastern Shore Estate

First Floor Studio Apartment in Historic Chestertown

Find spaces that suit your style

Family-friendly Rentals in Kent County

Holiday Rental options in Kent County