
Cottage rentals near Chesapeake Bay
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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

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

*Cottage @ Firefly Cellars* VA Wine Country escape

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

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

Poseidon - Beach Carriage House - 120 Years Old

3 BR Bay Home w Private Dock & all the Amenities
Pet-friendly cottage rentals

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

19th Century Coastal Cottage with Modern Amenities

Relaxing Water Views - Mill Creek Cottage

A "True" Chesapeake Bay Waterfront Experience!

TooFine Lakehouse, pet friendly waterfront cottage

Romantic Stone Cottage Circa 1869-75 acres to Hike

Historic Ware River Cottage at Glebefield

Newly Renovated 2BR Waterfront Cottage with Dock
Private cottage rentals

Cozy cottage 3 blocks from beach

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Charming Waterfront on Chesapeake Bay

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Weems Creek Cottage, Annapolis Waterfront

Creeks End Farmhouse

Waterfront Chesapeake Bay Sunrises & Private PIER!

Waterfront Cottage on the Potomac River
Luxury cottage rentals

Miracle on the James Cottage

Sandcastle directly ON the beach

Private Beach Access at The OV Beach House

Amazing, Secluded Luxury waterfront cottage!

Rodo Beach Cottage - Dog Friendly Private Beach wi

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
$85 NZD 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
- Bed and breakfasts Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- House rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay 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
- Chrysler Museum of Art
- Golden Horseshoe Golf Club
- James River Country Club
- Cape Charles Beachfront
- Wilkins Beach
- Wallops Beach
- Sarah Constant Beach Park