
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

Waterfront Cottage & Guesthouse Near Cambridge

Riverside Haven w/ Hot Tub

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

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

A "True" Chesapeake Bay Waterfront Experience!

Ft. Smallwood Overlook. Waterfront with Kayaks!

Creeks End Farmhouse

TooFine Lakehouse, pet friendly waterfront cottage
Private cottage rentals

The Little Anchor Cottage, St. Michaels, MD

Cozy cottage 3 blocks from beach

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Charming Waterfront on Chesapeake Bay

Cottage on the Bay - Kent Island

Weems Creek Cottage, Annapolis Waterfront

Waterfront Chesapeake Bay Sunrises & Private PIER!

Chesapeake Bay Beach Cottage
Luxury cottage rentals

Peaceful 5 bedroom cottage on the Eastern Shore...

Sandcastle directly ON the beach

Comfy three bedroom cottage - easy beach access

Newly Renovated Summer Paradise-Pool-Tennis-Garden

Bay cottage 🏖on the beach. Stunning views🏝

Very cosy and nicely appointed Waterfront Cottage

The Good Vibe Cottage

The Potomac House: 13 acre riverfront property
Quick stats about cottage rentals near Chesapeake Bay
Total rentals
360 properties
Nightly prices starting at
$69 CAD 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
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Loft rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Condo rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse 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
- Wilkins Beach
- Little Creek Beach
- Sarah Constant Beach Park