
Holiday houses in Chesapeake City
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Top-rated holiday rentals in Chesapeake City
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The Mint Cottage in Chesapeake City
The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Hygge Haven: A cozy apartment in a canal-side town
Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

Summer Season @ Old Lock View Chesapeake City MD
*We are Pet Friendly* Named for one of the original C&D Canal Locks, Old Lock View is a true breath of fresh air! Enjoy this recently renovated spacious older home with spacious rooms, plenty of off-street parking. Move from the indoor comfort to the outdoor entertaining patio with gazebo, BBQ grill, year-round outdoor firepits and patio table/chairs. Every detail has been thought of for your comfort. No parties Stay here when in town to attend family events like weddings and graduations etc.

Persimmon Pastures
A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Upper Chesapeake Getaway
Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Waterfront Retreat for Weekends and More!
NEW: 1-Hour south of the Philadelphia World Cup Games (FIFA)!!! Nature at its finest: Find peace and tranquility in this waterfront home with breathtaking water views from all freshly decorated rooms. Enjoy the water traffic on the C&D Canal along with the multitude of wildlife living in the area. Launch your kayak, canoe or row boat from the boat ramp. Relax here in the evenings while spending the day visiting the University of Delaware or other local Cecil County venues.

Waterfront Log Cabin with Hot Tub
Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Countryside-Stablehouse-Cozy for 2-March Discounts
Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

The Bohemia Charmer
Take it easy at this unique and tranquil getaway. In the Hack's Point Community, on the shores of the Bohemia River, this home will give you plenty of opportunities to relax, no matter the season. This home has the closest proximity to the community beach and pier, and it also exudes historic charm with a stunning 2-story fireplace, hardwood & stone flooring, and built-ins. ***There is no guest access to the pier for storage or day-use of boats***

Sunset River Shack -amazing waterfront view
Sunset River Shack is both Nauti and Nice!This awesome Nauti -Boho styled waterfront cottage has fantastic water views overlooking the Elk River on the Upper Chesapeake Bay. Sunsets all year long. The cottage is newly renovated and perfect for a romantic getaway, family vacay, boating trip, girls getaway, or no occasion at all. You'll never want to leave! Enjoy Chesapeake Bay life at Sunset River Shack.

Bohemia Bungalow
Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.
Popular amenities for Chesapeake City holiday rentals
Other great holiday rentals in Chesapeake City

Grandma’s Cottage

Riverfront Haven @ Hances Point

Casa Domino: A Peaceful Waterfront Retreat

Captain’s Cottage Retreat

Catching Sunsets on the Bay

Waterfront House on the Upper Chesapeake Bay

Tiny Bay House on Delaware Bay/2 Min Walk to Beach

Historic Chesapeake City Stay
When is the best time to visit Chesapeake City?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 AUD | $284 AUD | $372 AUD | $259 AUD | $289 AUD | $287 AUD | $297 AUD | $294 AUD | $388 AUD | $304 AUD | $305 AUD | $291 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 25°C | 24°C | 21°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Chesapeake City?
Accommodations in Chesapeake City are often found within the historic district, where you can enjoy canal views and walkable access to shops, restaurants, and the waterfront. Some stays are located in restored historic homes.
What are the best things to do in Chesapeake City with kids?
Chesapeake City has family-friendly trails along the canal, hands-on displays at the canal museum, and opportunities for ice cream breaks or casual waterfront dining. Look for seasonal art fairs and water activities designed for younger visitors.
What are some of the best things to do in Chesapeake City?
Chesapeake City has historic canal-side walks, galleries, and unique boutiques. Explore the Chesapeake and Delaware Canal Museum, relax at local eateries, or join a boat tour for scenic water views.
How is the weather in Chesapeake City?
Chesapeake City experiences cold winters near 26–41°F (-4–5°C) and warm, humid summers averaging 68–87°F (20–31°C). Spring and fall are milder, making outdoor activities and canal strolls more comfortable.
When is the best time to visit Chesapeake City?
Late spring and early fall are often recommended, with temperatures around 53–78°F (12–26°C) and comfortable weather for outdoor strolls and patio dining. Seasonal festivities and changing foliage add to the area's charm.
What are the best places to visit in Chesapeake City?
Chesapeake City has the Chesapeake and Delaware Canal Museum, local art galleries, and waterfront parks with views of passing boats. The historic district features restored buildings and boutique shops.
What are some hiking trails in Chesapeake City?
Chesapeake City has scenic canal paths suitable for walking, running, or cycling, with views of water traffic and native plants. Local parks around town also feature easy trails for a relaxed outdoor experience.
What are some family activities we can do in Chesapeake City?
Families can explore small parks, visit interactive exhibits at the Chesapeake and Delaware Canal Museum, or enjoy a boat tour together. Seasonal festivals and canal-side picnics are also frequently suggested.
What are some of the best day trip ideas from Chesapeake City?
Nearby, you can explore nature trails in regional parks, tour area wineries, or visit neighboring riverfront towns known for their arts scenes. The region also has seasonal farms and birdwatching locations.
Are there any pet friendly accommodations available in Chesapeake City?
Chesapeake City has pet-friendly stays, especially in the historic district and around the waterfront. Some properties provide outdoor space, making it easy for guests and their pets to relax together.
What are some local tips for visiting Chesapeake City?
Wear comfortable shoes for exploring the historic district’s brick walkways, and consider timing your visit with a boat parade or open-air market. Canal-side dining is a favorite local experience, especially in mild weather.
What is Chesapeake City known for?
Chesapeake City is known for its historic canal, charming 19th-century architecture, and vibrant arts and dining scene. Its location along the Chesapeake and Delaware Canal attracts boaters and history enthusiasts.
What are the best hidden gems to explore in Chesapeake City?
Explore the side streets for local artisan studios, quiet canal overlooks, and historic buildings with original architectural details. Around town, less-trafficked parks and vintage shops are often mentioned by locals.
What are the best foods to try in Chesapeake City?
Frequently suggested foods include locally inspired crab cakes, fresh seafood, and classic American comfort dishes. Many restaurants feature dishes rooted in the Chesapeake Bay region’s culinary traditions.
What should I bring for a trip to Chesapeake City?
Pack comfortable walking shoes for the historic district, a light jacket for evenings near the water, and an umbrella due to occasional rain. A camera is handy for capturing canal views and historic details.
What is the nightlife in Chesapeake City like?
Chesapeake City’s nightlife centers around cozy taverns, waterfront restaurants, and occasional live music venues. Evenings are relaxed, with canal views and local food often part of the experience.
What are the most popular events or festivals in Chesapeake City?
Chesapeake City hosts canal-related boat parades, antique or craft fairs, and seasonal celebrations, especially in spring and winter. Many people enjoy visiting during holiday markets and local art events.
Are there family friendly vacation rentals in Chesapeake City?
Chesapeake City has family-friendly vacation rentals, especially in the historic district and near the waterfront. Many places provide spacious layouts, kitchens, and amenities for comfortable group stays.
Quick stats about holiday rentals in Chesapeake City

Total holiday rentals
Explore 30 holiday rentals in Chesapeake City

Nightly prices starting at
Chesapeake City holiday rentals start at $125 AUD per night before taxes and fees

Verified guest reviews
Over 1,870 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake City holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Chesapeake City rentals

5 Average rating
Chesapeake City stays are highly rated by guests—averaging 5 out of 5!
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