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Sonic Drive-In offers classic American fast food with 100% pure beef burgers, hand-made onion rings, and real ice cream, all served with friendly carhops on roller skates in a nostalgic drive-in setting. It's a fun, quick, and convenient dining experience with a retro vibe.
The Nauti Goose offers savory seafood and refreshing drinks with stunning waterfront views on the North East River, featuring lively weekend entertainment and a welcoming nautical atmosphere perfect for dining, socializing, or special events. Dock your boat and enjoy the vibrant, relaxed vibe year-round.
Schaefer's Canal House offers fresh Maryland seafood classics like crab cakes and oysters, served with stunning views of the Chesapeake & Delaware Canal from its cozy dining room and veranda. It's a welcoming waterfront spot perfect for boaters and locals alike.
Chesapeake Inn Restaurant & Marina offers an upscale waterfront dining experience in historic Chesapeake City, featuring fresh seafood, sushi, and brick-oven pizzas with stunning views of the Chesapeake and Delaware Canal. Its lively deck and elegant dining room make it perfect for casual meals or special occasions.
Wawa offers made-to-order hoagies, fresh coffee, and a variety of hot breakfast and dinner options in a casual, 24-hour convenience store setting with ample seating. It’s a beloved East Coast chain known for quick, tasty meals anytime.
Prime 225 offers an elegant dining experience in historic Chesapeake City, featuring the finest prime steaks, fresh seafood, and carefully selected wines in a warm and inviting atmosphere.
UnWined on the Water offers a relaxed waterfront dining experience with a diverse menu of American and seafood dishes, complemented by an extensive wine list and craft cocktails. Its spacious outdoor patio is perfect for enjoying meals with your dog by your side.
Olive Garden offers hearty Italian-American classics in a warm, family-friendly setting, known for its fresh soups, endless breadsticks, and generous portions that bring a comforting taste of Italy to every meal.
The Bayard House Restaurant offers fresh, flavorful seafood in a historic 18th-century setting right on the Chesapeake City waterfront, complete with scenic canal views and a charming, classic ambiance. Its blend of rich history and delicious cuisine creates a memorable dining experience.
Sonny’s Italian Market and Deli serves up classic Italian-American favorites like award-winning hoagies and cheesesteaks in a welcoming, casual setting that caters to all tastes, including vegetarian options.
North East Community Park offers scenic waterfront views, a playground, picnic pavilions, and the unique Upper Bay Museum showcasing local maritime history. It’s perfect for families, nature lovers, and anyone seeking a peaceful spot to relax or kayak on the North East River.
Woodlands Camping Resort offers a family-friendly getaway with spacious wooded sites, a large swimming pool, playground, and plenty of outdoor activities like hiking and sports courts, perfect for campers seeking relaxation and fun in nature year-round. Veterans are honored here with a special memorial area.
Charlestown Manor Beach and Campground offers a peaceful waterfront escape with clean facilities, perfect for swimming, kayaking, fishing, and relaxing picnics. It’s ideal for outdoor lovers seeking both adventure and tranquility in a friendly, scenic setting.
Bohemia River State Park offers peaceful trails through diverse habitats and scenic river views, perfect for nature lovers, bird watchers, and paddlers seeking a quiet outdoor escape. Its gentle terrain and upcoming kayak launch make it ideal for families and beginners.
Brantwood Regional Park offers a fun playground with unique swings, slides, and a zip line, plus a paved story trail perfect for families and kids who love adventure and outdoor play. Nature lovers will enjoy the walking paths and nearby pond.
Meadow Park offers a lively mix of sports courts, a playground, and a community garden perfect for families and active visitors looking to enjoy outdoor fun and fitness in a friendly neighborhood setting.
Elk Neck State Forest offers peaceful hiking through diverse trails, birdwatching in a nationally recognized Important Bird Area, and unique outdoor experiences like archery and shooting ranges. Nature lovers and outdoor enthusiasts will enjoy its scenic beauty and variety of activities.
The Ben Cardin C&D Canal Trail offers a scenic, paved route along the canal perfect for biking, walking, and wildlife viewing. Ideal for families and outdoor enthusiasts seeking peaceful nature views and easy access to charming Chesapeake City’s shops and eateries.
The C & D Canal Museum offers a fascinating glimpse into the history and engineering of one of America’s most important sea-level canals, featuring original canal engines and detailed exhibits. History buffs and curious travelers will enjoy exploring this hidden gem in charming Chesapeake City.

Guests love the hot tub, private beach and dock plus plenty of water activities like kayaks. They praise the peaceful waterfront location with stunning views, the spotless home and the hosts' very responsive concierge service. Perfect for large family gatherings.
Quiet hours are from 10 PM to 8 AM. We kindly ask that you refrain from hosting parties or creating excessive noise during your stay, as we strive to maintain a peaceful environment for both our guests and neighbors. Amplified outdoor sounds are strictly prohibited.
This home contains features that may be difficult for elderly and guests with mobility challenges - including climbing a set of stairs to access additional levels.
This home follows a strict maximum occupancy rule of 20 guests. Please make sure that the total number of guests accompanying you (including both children and adults) doesn’t exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.
This is a pet-free hypoallergenic space. No pets are allowed inside the home to maintain a hypoallergenic area as much as possible for our guests’ comfort.
Parties & Events
Hosting parties and events is not allowed in this home without prior approval. Please reach out to Concierge with your request.
Early Check-In
There are no early check-ins allowed in this home without prior approval.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 5, 2025 | $1067 | Available |
| Dec 6, 2025 | $1067 | Available |
| Dec 7, 2025 | $1067 | Available |
| Dec 8, 2025 | $1067 | Available |
| Dec 9, 2025 | $1067 | Available |
| Dec 10, 2025 | $1067 | Available |
| Dec 11, 2025 | $1067 | Available |
| Dec 12, 2025 | $1067 | Available |
| Dec 13, 2025 | $1067 | Available |
| Dec 14, 2025 | $1067 | Available |
| Dec 15, 2025 | $1067 | Available |
| Dec 16, 2025 | $1067 | Available |
| Dec 17, 2025 | $1067 | Available |
| Dec 18, 2025 | $1067 | Available |
| Dec 19, 2025 | $1067 | Available |
| Dec 20, 2025 | $1067 | Available |
| Dec 21, 2025 | $1067 | Not Available |
| Dec 22, 2025 | $1067 | Not Available |
| Dec 23, 2025 | $1067 | Not Available |
| Dec 24, 2025 | $1067 | Not Available |
| Dec 25, 2025 | $1067 | Not Available |
| Dec 26, 2025 | $1319 | Not Available |
| Dec 27, 2025 | $1279 | Not Available |
| Dec 28, 2025 | $1178 | Not Available |
| Dec 29, 2025 | $1200 | Not Available |
| Dec 30, 2025 | $1192 | Not Available |
| Dec 31, 2025 | $1231 | Not Available |
| Jan 1, 2026 | $1067 | Not Available |
| Jan 2, 2026 | $1067 | Not Available |
| Jan 3, 2026 | $1067 | Not Available |
| Jan 4, 2026 | $950 | Available |
| Jan 5, 2026 | $950 | Available |
| Jan 6, 2026 | $950 | Available |
| Jan 7, 2026 | $950 | Available |
| Jan 8, 2026 | $950 | Available |
| Jan 9, 2026 | $950 | Available |
| Jan 10, 2026 | $950 | Available |
| Jan 11, 2026 | $950 | Available |
| Jan 12, 2026 | $950 | Available |
| Jan 13, 2026 | $950 | Available |
| Jan 14, 2026 | $950 | Available |
| Jan 15, 2026 | $950 | Available |
| Jan 16, 2026 | $950 | Available |
| Jan 17, 2026 | $950 | Available |
| Jan 18, 2026 | $950 | Available |
| Jan 19, 2026 | $950 | Available |
| Jan 20, 2026 | $950 | Available |
| Jan 21, 2026 | $950 | Available |
| Jan 22, 2026 | $950 | Available |
| Jan 23, 2026 | $950 | Available |
| Jan 24, 2026 | $950 | Available |
| Jan 25, 2026 | $950 | Available |
| Jan 26, 2026 | $950 | Available |
| Jan 27, 2026 | $950 | Available |
| Jan 28, 2026 | $950 | Available |
| Jan 29, 2026 | $950 | Available |
| Jan 30, 2026 | $950 | Available |
| Jan 31, 2026 | $950 | Available |
| Feb 1, 2026 | $980 | Available |
| Feb 2, 2026 | $980 | Available |
| Feb 3, 2026 | $980 | Available |
| Feb 4, 2026 | $980 | Available |
| Feb 5, 2026 | $980 | Available |
| Feb 6, 2026 | $980 | Available |
| Feb 7, 2026 | $980 | Available |
| Feb 8, 2026 | $980 | Available |
| Feb 9, 2026 | $980 | Available |
| Feb 10, 2026 | $980 | Available |
| Feb 11, 2026 | $980 | Available |
| Feb 12, 2026 | $980 | Available |
| Feb 13, 2026 | $980 | Available |
| Feb 14, 2026 | $980 | Available |
| Feb 15, 2026 | $980 | Available |
| Feb 16, 2026 | $980 | Available |
| Feb 17, 2026 | $980 | Available |
| Feb 18, 2026 | $980 | Available |
| Feb 19, 2026 | $980 | Available |
| Feb 20, 2026 | $980 | Available |
| Feb 21, 2026 | $980 | Available |
| Feb 22, 2026 | $980 | Available |
| Feb 23, 2026 | $980 | Available |
| Feb 24, 2026 | $980 | Available |
| Feb 25, 2026 | $980 | Available |
| Feb 26, 2026 | $980 | Available |
| Feb 27, 2026 | $980 | Available |
| Feb 28, 2026 | $980 | Available |
| Mar 1, 2026 | $1067 | Available |
| Mar 2, 2026 | $1067 | Available |
| Mar 3, 2026 | $1067 | Available |
| Mar 4, 2026 | $1067 | Available |
| Mar 5, 2026 | $1067 | Not Available |