Dorchester County family rentals

We found 440 family rentals — enter your dates for availability

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November 2025

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December 2025

Find the best place to stay - Dorchester County

Showing deals for: 19 Feb - 22 Feb

Magnificent property for crabbing, fishing, volleyball and badmitten

Premier Host

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Sleeps 28 · 7 bedrooms · 6+ bathrooms

for 3 nights, 1 home

NZ$2,625 per night

includes taxes & fees

Property grounds

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

Sleeps 40 · 12 bedrooms · 8+ bathrooms

for 3 nights, 1 home

NZ$3,251 per night

includes taxes & fees

Comfortable, Spacious, Family-Friendly Second living room

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Sleeps 22 · 8 bedrooms · 6 bathrooms

for 3 nights, 1 home

NZ$2,637 per night

includes taxes & fees

Aerial view

Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate

Sleeps 60 · 20 bedrooms · 16+ bathrooms

for 3 nights, 1 home

NZ$13,644 per night

includes taxes & fees

A beautiful view of our pier. Photo credit: @ebb.creativemarketing

Premier Host

Waterfront Cottage in Beautiful Hoopers Island

Sleeps 5 · 2 bedrooms · 1 bathroom

for 3 nights, 1 cottage

NZ$592 per night

includes taxes & fees

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Family-friendly Rentals in Dorchester County

Holiday Rental options in Dorchester County

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