
Places to stay near Chesapeake Bay
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Top-rated holiday rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
Popular amenities for holiday rentals near Chesapeake Bay
Other top sights near Chesapeake Bay
Apartment rentals with wifi

The Bird's Nest in Historic Occoquan (Mins to DC)

Dewey Beach Condo 2BR+sofa bed. Walk to the beach!

Cozy Oxford Getaway

Casa 1776 - Spacious Apartment | Heart of Downtown

Newly Renovated 1BR Condo Sleeps 2 - Unit 1

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

Direct Oceanfront close to Northside Park!

The Hideaway By The Bay OCMD
Family-friendly house rentals

Tiny House at Good Earth, near Bethany Beach

Cove Point Beach Cabin

Newly Renovated Modern 3 bed 2 bath Water Front

Camp Rappahannock - Deltaville Waterfront Living

Cozy Riverside Cottage in the Woods

"Queen Bee “ WATERVIEW & WALK TO ACCESS the River

Gorgeous Waterfront Home!

3 bedroom/2.5 bath Smith Island bungalow with dock
Apartment rentals with air conditioning

Our Little Piece of Heaven

Walk to famous Tiki Bar on Solomons Island!

Stunning Sunsets on Breton Bay, Seaside apartment

Private cozy cottage - center of Chestertown .

Historic St. Mary's City, MD

Serenity Suite on Chesapeake Bay

Little Cove Cottage, Couples Retreat/Mathews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
Other great holiday rentals near Chesapeake Bay

Riverfront Chalet Kayak/Canoe, pier, breakfast!

A "True" Chesapeake Bay Waterfront Experience!

The Laughing King Retreat Honeymoon Island Cottage

Private Guesthouse on Secluded Waterfront Farm

Good Vibe Villa, Tiny houseboat

Beach Please! River cottage w/private beach & dock

Kent Island Waterfront Home with Amazing Sunsets

Waterfront Getaway - View of bay from your bed
Destinations to explore
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
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- Rentals with an EV charger Chesapeake Bay
- Rentals with a patio Chesapeake Bay
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- Townhouse rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
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- Family-friendly rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
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- Resort rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Assateague Beach
- Kingsmill Resort
- Outlook Beach
- Haven Beach
- Jamestown Settlement
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Kiptopeke Beach
- Wilkins Beach
- Wallops Beach
- Piney Point Beach
- Little Creek Beach
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Yurt Rentals United States
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