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

Outdoor Explorer's Dream Studio,James River Park

Annapolis Guesthouse - Completely Separate Space

Cozy Carriage House

Carriage House near Navy Stadium, parking, pets

The Shady Bear Cabin

Private Luxury Retreat Close to everything!

Bonfield Bungalow

Woodland Retreat
Guest house rentals with a patio

Casita Del Ray — Alexandria Studio Apartment

BlueBird Nest

Creekside Guesthouse - Dock and Pool on 10 acres

Little Green Guesthouse

Fox Cottage *Pet Friendly*

DC Treehouse - Charming, private 1-bdrm ADU in DC

Sunny Guesthouse steps from Towson!

"Lofty Cottage" Adorable 1-Bedroom Guest House
Guest house rentals with a washing machine and dryer

Sunny, Stylish Carriage House with a View

Private Art-Filled Guesthouse near Naval Academy

Luxurious 1Bed Carriage House, 1.5 Blocks to Metro

Private Country Guesthouse Getaway Minutes from UD

"L'auberge du Cape Saint Claire"

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

Chesapeake Bay Escape | Cozy Retreat

Capitol Hill Carriage House
Other guest house holiday rentals

Heron’s Landing II

La Casita

NEWLY Renovated -- Waterfront Getaway

The Garden Studio

Studio on the Bay.

Chesapeake Birdhouse Studio

Annapolis Loft Apartment- separate space

2 Level Guest House-Spotless & Private-Parking
Quick stats about guest house rentals near Chesapeake Bay
Total rentals
160 properties
Total number of reviews
11K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
- House rentals Chesapeake Bay
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- Guest house rentals United States
- Virginia Beach Oceanfront
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- Kingsmill Resort
- First Landing State Park
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- Assateague Beach
- Grandview Beach
- Haven Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Jamestown Settlement
- Kiptopeke Beach
- Sarah Constant Beach Park
- Norfolk Botanical Garden
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- Golden Horseshoe Golf Club
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- Chrysler Museum of Art
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