Caroline County family rentals

We found 52 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Caroline County

Showing deals for: 18 Feb - 21 Feb

Denton Vacation Rental | 5BR | 3.5BA | 4,496 Sq Ft | 4 Steps Required

Riverfront Denton Estate on 7 Acres w/ Heated Pool

Sleeps 16 · 5 bedrooms · 3+ bathrooms

for 3 nights, 1 home

NZ$1,162 per night

includes taxes & fees

Premier Host

Stylish Home on the Choptank River (with Tidal Beach)

Sleeps 6 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$541 per night

includes taxes & fees

Premier Host

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Sleeps 8 · 2 bedrooms · 2+ bathrooms

for 3 nights, 1 room

NZ$679 per night

includes taxes & fees

Premier Host

Relaxation Haven on the Shore near Choptank River

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

NZ$519 per night

includes taxes & fees

250 ACRE RETREAT CHESAPEAKE BAY VACATION/REUNION/WEDDING 12 BEDROOMS, SLEEPS 40

Sleeps 40 · 12 bedrooms · 8+ bathrooms

for 3 nights, 1 home

NZ$3,238 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Caroline County

Riverfront Denton Estate on 7 Acres w/ Heated Pool

Stylish Home on the Choptank River (with Tidal Beach)

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Relaxation Haven on the Shore near Choptank River

Turnbridge Manor

250 ACRE RETREAT CHESAPEAKE BAY VACATION/REUNION/WEDDING 12 BEDROOMS, SLEEPS 40

Find spaces that suit your style

Family-friendly Rentals in Caroline County

Holiday Rental options in Caroline County