
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

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

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

Chapel Cottage HdG

Hot Tub Hideaway by Shark Tooth Shores

Poseidon - Beach Carriage House - 120 Years Old

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

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

19th Century Coastal Cottage with Modern Amenities

Relaxing Water Views - Mill Creek Cottage

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

"Bee Haven" Cottage Retreat

Cottage by the bay (private peaceful surroundings)

Charming Waterfront Home with Expansive Views

TooFine Lakehouse, pet friendly waterfront cottage
Private cottage rentals

Cozy cottage 3 blocks from beach

The Moore Cottage

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Charming Waterfront on Chesapeake Bay

Bell Farm Cottage LLC - quiet and peaceful

Levering Creek Cottage with Private Dock

Sarah's Creek Starlight

Waterfront Chesapeake Bay Sunrises & Private PIER!
Luxury cottage rentals

The Ladybug - arcade, dog-friendly, firepit, & EV

Comfy three bedroom cottage - easy beach access

Private Beach Access at The OV Beach House

Weems Creek Cottage, Annapolis Waterfront

Bay cottage 🏖on the beach. Stunning views🏝

Sea Salt Cottage: Tranquil Getaway 5 min to beach

The Potomac House: 13 acre riverfront property

Waterfront Bay Cottage w/ Your Own Private Beach
Quick stats about cottage rentals near Chesapeake Bay
Total rentals
360 properties
Nightly prices starting at
€ 43 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
- Beachfront rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Villa rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Cottage rentals United States
- 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
- Little Creek Beach
- Cape Charles Beachfront
- Piney Point Beach
- Sarah Constant Beach Park
- Wallops Beach