
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

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

Room with Balcony/View

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

Cozy Santorini Room at Grandiflora Wine Garden!

Farmhouse Elegance: Historic Inn Retreat - 301

Carroll Valley Stay | Golf View Double Room

Romantic Victorian Castle SuiteJ

Armistead House - Room 302 (3rd Floor)

The Charlesworth Hotel and Restaurant on the Bay

Armistead House - Room 201 (2nd Floor)

Armistead House - Room 301 (3rd Floor)
Other boutique hotel holiday rentals

The Laughing King Retreat, Cedar Island Suite

Elegant King Room Near Convention Center & Museums

Classified Moto - The El Mayor Room

Charming, renovated loft at Quiet Sun Resort

Four Eleven York Suite Two Bed Room

#1 Place to Stay by TripAdvisor & Bfast 4 Foodies

ARC Hotel, View King

Excellent Choice! Enjoy Outdoor & Indoor Pools!
Quick stats about boutique hotel rentals near Chesapeake Bay
Total rentals
80 properties
Nightly prices starting at
€ 59 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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