
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

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Sunset River Shack -amazing waterfront view

Riverside Haven w/ Hot Tub

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

Hot Tub Hideaway by Shark Tooth Shores

Chapel Cottage HdG

Poseidon - Beach Carriage House - 120 Years Old

Old Log Cabin School House w/10 acres on the Bay
Pet-friendly cottage rentals

19th Century Coastal Cottage with Modern Amenities

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

"Bee Haven" Cottage Retreat

A "True" Chesapeake Bay Waterfront Experience!

Ft. Smallwood Overlook. Waterfront with Kayaks!

Charming Waterfront Home with Expansive Views

TooFine Lakehouse, pet friendly waterfront cottage

Historic Ware River Cottage at Glebefield
Private cottage rentals

The Little Anchor Cottage, St. Michaels, MD

Cozy cottage 3 blocks from beach

The Moore Cottage

Cottage with a view!

Chesapeake Bay Cottage

Levering Creek Cottage with Private Dock

Sarah's Creek Starlight

Waterfront Chesapeake Bay Sunrises w/Private PIER!
Luxury cottage rentals

Peaceful 5 bedroom cottage on the Eastern Shore...

Waterfront Cottage 3BR 2 BA, Pier, Sunsets,Kayaks

Clarendon: Metro Dog-friendly 40" Roku Park Patio

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Sanctuary on Sandpiper - Bayfront in Sandbridge

Cottage on the Bay - Kent Island

Weems Creek Cottage, Annapolis Waterfront

Sea Salt Cottage: Tranquil Getaway 5 min to beach
Quick stats about cottage rentals near Chesapeake Bay
Total rentals
360 properties
Nightly prices starting at
G$10,449 GYD 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
- Beach house rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- House rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Condo rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Kid-friendly rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Kingsmill Resort
- First Landing State Park
- Buckroe Beach and Park
- Assateague Beach
- Grandview Beach
- Haven Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Jamestown Settlement
- Kiptopeke Beach
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Piney Point Beach
- Wilkins Beach
- Little Creek Beach
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Wallops Beach
- Chrysler Museum of Art
- Cabins United States
- Treehouses United States
- Tiny Houses United States
- Beach Houses United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom