
Cottage rentals near Chesapeake Bay
Find and book unique cottages on Airbnb
Top-rated cottage rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
Popular amenities for cottage rentals near Chesapeake Bay
Cottage rentals with a hot tub

Block to Private Beach, Screened deck, Hot Tub

Riverside Haven w/ Hot Tub

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Chapel Cottage HdG

Poseidon - Beach Carriage House - 120 Years Old
Pet-friendly cottage rentals

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

19th Century Coastal Cottage with Modern Amenities

Relaxing Water Views - Mill Creek Cottage

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

"Bee Haven" Cottage Retreat

A "True" Chesapeake Bay Waterfront Experience!

Ft. Smallwood Overlook. Waterfront with Kayaks!

TooFine Lakehouse, pet friendly waterfront cottage
Private cottage rentals

Cozy cottage 3 blocks from beach

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Charming Waterfront on Chesapeake Bay

Chesapeake Bay Cottage

Private Beach Access at The OV Beach House

Weems Creek Cottage, Annapolis Waterfront

Waterfront Chesapeake Bay Sunrises & Private PIER!

Historic Ware River Cottage at Glebefield
Luxury cottage rentals

Sandcastle directly ON the beach

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Sanctuary on Sandpiper - Bayfront in Sandbridge

Cottage on the Bay - Kent Island

Rodo Beach Cottage - Dog Friendly Private Beach wi

Sunset Lagoon Home

Very cosy and nicely appointed Waterfront Cottage

The Good Vibe Cottage
Quick stats about cottage rentals near Chesapeake Bay
Total rentals
360 properties
Nightly prices starting at
$64 SGD before taxes and fees
Total number of reviews
27K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Resort rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Villa rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Flat rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Loft rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Cottage rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Assateague Beach
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Piney Point Beach
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Little Creek Beach
- Wilkins Beach
- Sarah Constant Beach Park