
Places to stay near Chesapeake Bay
Book unique holiday rentals, homes and more on Airbnb
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)

Cozy Oxford Getaway

Casa 1776 - Spacious Apartment | Heart of Downtown

Lux in heart of DC social scene, free parking!

Newly Renovated 1BR Condo Sleeps 2 - Unit 1

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

Luxury 1bd in Heart of Tysons
Family-friendly house rentals

Osprey's roost: Spring and summer 2025

Cove Point Beach Cabin

Newly Renovated Modern 3 bed 2 bath Water Front

Cozy Riverside Cottage in the Woods

Gorgeous Waterfront Home!

"Queen Bee “ WATERVIEW & WALK TO ACCESS the River

3 bedroom/2.5 bath Smith Island bungalow with dock

Top of the Chesapeake - Private Waterfront Home
Apartment rentals with air conditioning

Our Little Piece of Heaven

The Fish House

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

Beach Highway Hobby Farm

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

Peace Point - Waterfront, Secluded, Home w/hot tub

Peaceful Haven: nature, pool & charming town

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Private Guesthouse on Secluded Waterfront Farm

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Hutch's Bluff - Waterfront near Williamsburg

Hideaway on the Bay: Waterfront Vintage A Frame

Waterfront Cottage Getaway Pool/Kayaks/Fire Pit
Destinations to explore
- Waterfront rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Resort rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Flat rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Bethel Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Assateague Beach
- Haven Beach
- Outlook Beach
- Jamestown Settlement
- Sarah Constant Beach Park
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Kiptopeke Beach
- Chrysler Museum of Art
- Piney Point Beach
- Little Creek Beach
- Gargathy Beach
- Golden Horseshoe Golf Club
- Salt Ponds Public Beach
- 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