
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
ﺩ.ﺇ184 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
- Resort rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- House rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Villa rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Townhouse 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