
Boutique hotel holiday rentals near Chesapeake Bay
Find and book unique boutique hotel rentals on Airbnb
Top-rated boutique hotel rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
Popular amenities for boutique hotel rentals near Chesapeake Bay
Family-friendly boutique hotel rentals

The Stockett Room at the Vandiver Inn

Charming Boutique on C&O Canal ~ Workspace! Lock11

Vandiver's Stokes Room: Porch overlooking the gardens and walk-in shower!

The Tydings at the Vandiver: Victorian elegance, stunning fireplace and king bed.

The Cockburn Room at the Vandiver Inn

The Donahoo Room at the Vandiver Inn

The Fair Room at the Vandiver Inn

Vandiver's Young Room: Funky and adorable space
Boutique hotel rentals with a patio

Romantic Victorian Castle SuiteK

Peacock Grand SPA Suite

Romantic Victorian Castle SuiteV

Cozy Santorini Room at Grandiflora Wine Garden!

Farmhouse Elegance: Historic Inn Retreat - 301

Romantic Victorian Castle SuiteJ

Armistead House - Room 302 (3rd Floor)

The Charlesworth Hotel and Restaurant on the Bay
Other great holiday rentals near Chesapeake Bay

Private romantic pet friendly waterfront cottage

The Crab House - a Private, Waterfront Guest House

Little Dipper -private beach,Kayaks & paddleboards

Good Vibe Villa, Tiny houseboat

Sunset Breezes - quiet waterfront retreat

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Waterfront Getaway - View of bay from your bed

White Point Cottage -- Quiet Waterfront Getaway
Quick stats about boutique hotel rentals near Chesapeake Bay
Total rentals
80 properties
Nightly prices starting at
€ 60 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
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