
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

Mom's Cottage

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

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

Poseidon - Beach Carriage House - 120 Years Old

Old Log Cabin School House w/10 acres on the Bay

3 BR Bay Home w Private Dock & all the Amenities
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

Charming Waterfront Home with Expansive Views

Creeks End Farmhouse

TooFine Lakehouse, pet friendly waterfront cottage
Private cottage rentals

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Cozy cottage 3 blocks from beach

The Moore Cottage

Charming Waterfront on Chesapeake Bay

Chesapeake Bay Cottage

Levering Creek Cottage with Private Dock

Sarah's Creek Starlight

Weems Creek Cottage, Annapolis Waterfront
Luxury cottage rentals

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

Peaceful 5 bedroom cottage on the Eastern Shore...

Sandcastle directly ON the beach

Sanctuary on Sandpiper - Bayfront in Sandbridge

Cottage on the Bay - Kent Island

The Potomac House: 13 acre riverfront property

Waterfront Bay Cottage w/ Your Own Private Beach

Ebb & Flow Beach House - Lewes Bay Beach Retreat
Quick stats about cottage rentals near Chesapeake Bay
Total rentals
360 properties
Nightly prices starting at
$50 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
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Cottage rentals United States
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