Caroline County pet-friendly rentals

We found 19 pet-friendly rentals — enter your dates for availability

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October 2025

November 2025

Explore Caroline County pet-friendly rentals

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

Premier Host

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Sleeps 6 · 2 bedrooms · 2 bathrooms

Our Chrisy & Cooper on our dock with rowboat (hand-built Annapolis Wherry,)

Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm

Sleeps 6 · 2 bedrooms · 1 bathroom

Premier Host

Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat

Sleeps 10 · 5 bedrooms · 3+ bathrooms

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Pet-friendly Rentals in Caroline County

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Pet-friendly Rentals in Denton

Pet-friendly Rentals in Federalsburg

Holiday Rental options in Caroline County

Family-friendly holiday rentals in Caroline County

Mountain holiday rentals in Caroline County

Holiday rentals with spa pool in Caroline County

Oceanfront holiday rentals in Caroline County

Beach holiday rentals in Caroline County

Lake holiday rentals in Caroline County

Ski holiday rentals in Caroline County

Holiday rentals with pool in Caroline County

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