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Cottages in Chesapeake Beach

Our top choices for Chesapeake Beach cottages

6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Interior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Front of property

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Walk to Beach: Charming Maryland Home w/ Yard!
House (2 Bedrooms) | Interior

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Exterior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage (2 Bedrooms) | Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very Good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
House (4 Bedrooms) | Interior

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Updated North Beach Cottage: Pet Friendly!
Cottage (3 Bedrooms) | Front of property

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Bayfront Gem w/ Amazing Water Views + Pond!
Front of property

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Tranquil Port Republic Home w/ Water Views!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
House (1 Bedroom) | Interior

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bayfront Maryland Retreat w/ Deck, Near Beaches!
House (3 Bedrooms) | Front of property

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Waterfront Home w/ Hot Tub in Bozman Village!
House (4 Bedrooms) | Interior

Waterfront Home w/ Hot Tub in Bozman Village!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!
Water-view Deale Home: Walk to Marina, Restaurants
House (5 Bedrooms) | Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
Waterfront Cambridge Home: Pool & Dock!
House (4 Bedrooms) | Interior

Waterfront Cambridge Home: Pool & Dock!

3.0 star property
Waterfront Cambridge Home: Pool & Dock!
Coastal Edgewater Home w/ Private Hot Tub!
House (5 Bedrooms) | Interior

Coastal Edgewater Home w/ Private Hot Tub!

3.0 star property
Coastal Edgewater Home w/ Private Hot Tub!
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
House (2 Bedrooms) | Interior

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

3.0 star property
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Walk to Beach: Elegant Escape in Lusby!
House (4 Bedrooms) | Interior

Walk to Beach: Elegant Escape in Lusby!

3.0 star property
Walk to Beach: Elegant Escape in Lusby!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Beach Hotel Reviews

Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

10/10 Excellent
"For what we paid, it was a great hotel. It was clean and quiet. There was ample parking and the front desk was professional. Its not luxury but I didnt pay for luxury. Felt it was worth it and its near alot of things. Not walkable, but its drivable. Near other hotels. "
Melone 1-night trip
Posted 2 days ago
Wingate by Wyndham Waldorf/Washington DC Area

Find out more about Chesapeake Beach

Find out more about Chesapeake Beach

Chesapeake Beach Cottages information

Number of reviews
4
Accommodation
32 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Chesapeake Beach with Expedia?
Expedia has some terrific cottages in Chesapeake Beach, so start planning for an unforgettable stay on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a pool or a kitchen. We'll help you find the perfect digs whatever your plans or style of travel.
How can I find cheap cottages in Chesapeake Beach?
The easiest way to score cheap cottages in Chesapeake Beach is with Expedia's useful filter tool. Narrow down your search by budget, star rating and amenities to land excellent rates with only a few clicks.
What is there to do in Chesapeake Beach near my cottage?
The perfect travel accessory is a well-planned to-do list. Breezy Point Beach is a good place to begin your sightseeing in Chesapeake Beach.

Explore a world of travel with Expedia

Explore a world of travel with Expedia