Caroline County beach rentals

We found 3 beach rentals — enter your dates for availability

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November 2025

December 2025

Explore Caroline County beach rentals

Showing deals for: 8 Feb - 11 Feb

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

Sleeps 40 · 12 bedrooms · 8+ bathrooms

for 3 nights, 1 home

AU$2,797 per night

includes taxes & fees

Premier Host

Swartzentruber Cottage close to DE Turf & Beaches, also for traveling nurses!

Sleeps 5 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$246 per night

includes taxes & fees

Premier Host

25-50% Off~Private Beach~Hot Tub~Fire Table~

Sleeps 7 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$676 per night

includes taxes & fees

Premier Host

Hidden Gem, Relax, Water Views, Bay Breezes Elevator & Decks & Hot Tub

Sleeps 9 · 5 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$2,480 per night

includes taxes & fees

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

Premier Host

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Sleeps 20 · 5 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$845 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Explore Caroline County beach rentals

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

Grandma's Cottage Milford Delaware

Swartzentruber Cottage close to DE Turf & Beaches, also for traveling nurses!

25-50% Off~Private Beach~Hot Tub~Fire Table~

Hidden Gem, Relax, Water Views, Bay Breezes Elevator & Decks & Hot Tub

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Find spaces that suit your style

Beach Rentals in Caroline County

Holiday Rental options in Caroline County