
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

The Grand Delphey: Downtown Artist Retreat

Casa 1776 - Spacious Apartment | Heart of Downtown

Lux in heart of DC social scene, free parking!

Beach Condo Block Off Boardwalk

Luxury Riverfront Condo w/ sunrise & sunset views

Private Apt-Old Town Alexandria-Self Check In
Family-friendly house rentals

Soul Oasis - home on the Chesapeake Bay

Cove Point Beach Cabin

1891 Coastal Charmer: fully renovated farmhouse

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Waterfront Farmhouse Meets Modern Luxury

Spacious Gorgeous Waterfront Home with Sunset View

Beach Please! River cottage w/private beach & dock

White Point Cottage -- Quiet Waterfront Getaway
Apartment rentals with air conditioning

Our Little Piece of Heaven

The Fish House

2nd floor studio apartment

Stunning Sunsets on Breton Bay, Seaside apartment

Private cozy cottage - center of Chestertown .

Serenity Suite on Chesapeake Bay

Beach Highway Hobby Farm

Charming Studio in the heart of St. Michael's, MD.
Other great holiday rentals near Chesapeake Bay

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

A "True" Chesapeake Bay Waterfront Experience!

Waterfront Barn Loft with Modern Cabin Vibe

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Lakeside Studio Retreat.

Waterfront Cottage in Colonial Beach at Placid Bay
Quick stats about holiday rentals near Chesapeake Bay
Total rentals
6.9K properties
Total number of reviews
272K reviews
Family-friendly rentals
4.6K properties are a good fit for families
Pet-friendly rentals
2.7K properties allow pets
Rentals with a pool
840 properties have a pool
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Destinations to explore
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Flat rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Assateague Beach
- Haven Beach
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Jamestown Settlement
- Outlook Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- James River Country Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Little Creek Beach
- Piney Point Beach
- Sarah Constant Beach Park
- Wallops Beach