Dorchester County vacation rentals

We found 452 vacation rentals — enter your dates for availability

Discover a selection of 119 homes, 14 apartments, and other vacation rentals in Dorchester County that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, like air conditioning and WiFi. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Dorchester County destinations on Vrbo

Holiday rentals with weekly discounts - Dorchester County

Showing deals for:Sep 18 - Sep 25

Find out more about Dorchester County

Why visit Dorchester County

  • Outdoor Adventures: Enjoy a variety of activities from kayaking to hiking, surrounded by stunning natural scenery.
  • Rich History: Delve into local heritage at historic sites that showcase the county's unique past.
  • Charming Neighborhoods: Explore quaint communities that offer a taste of suburban living and local culture.
  • Waterway Access: Relax by beautiful waterways, perfect for fishing, boating, and wildlife watching.
  • Diverse Accommodations: Choose from cozy cottages to modern apartments, ensuring a comfortable stay for every traveler.

Popular types of accommodation in Dorchester County

If you’re exploring vacation rentals in Dorchester County, you’ll find a variety of popular accommodations to suit your needs. From charming houses and cozy cottages to modern apartments, there’s something for everyone. Enjoy features like back porches for relaxation, granite counters for a touch of luxury, and easy access to local parks. Discover the perfect getaway that offers both comfort and convenience in this beautiful destination.

  • Houses: The top choice for visitors to Dorchester County, these homes offer plenty of space and comfort, perfect for families or groups looking to create lasting memories.
  • Cottages: A charming option for a cozy getaway, cottages provide a quaint atmosphere and often feature beautiful surroundings, ideal for couples or solo travelers.
  • Apartments: A practical choice for those seeking convenience, apartments offer a home-like feel with essential amenities for a comfortable stay.**

Top attractions in Dorchester County

Dorchester County, Maryland, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Visitors can explore beautiful islands, relax in urban parks, and delve into the area's rich history at local historic sites. Whether you're looking for a beach getaway or a cultural experience, Dorchester County has something for everyone, making it an ideal destination for your next vacation.

Things to do recommended for couples

For a romantic getaway in Dorchester County, visit Layton's Chance Vineyard and Winery. Enjoy a cozy wine tasting experience amidst beautiful scenery, perfect for couples seeking romance and entertainment. Savor the flavors of locally crafted wines while creating unforgettable memories together.

Things to do recommended for families

Families can explore the scenic beauty of the Blackwater National Wildlife Refuge, where kids can spot wildlife and enjoy hiking trails. Don't miss the chance to visit the Harriet Tubman Underground Railroad Visitor Center for an educational experience that highlights local history.

Things to do recommended for groups

Explore the unique offerings at Bay Country Shop, where your group can find local crafts and souvenirs. Enjoy the charm of Dorchester County while sampling local delicacies and shopping for handmade goods to remember your trip by.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Dorchester County

When traveling with a group, family, pets, or planning for extended stays, it's important to prioritize your preferences while searching. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Dorchester County with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Dorchester County with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, considering how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Dorchester County: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Dorchester County: If you're in search of vacation rentals with discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Dorchester County

Exploring Dorchester County, Maryland, offers a delightful blend of outdoor adventures and picturesque scenery. This charming county is perfect for romantic getaways and family-friendly activities. Discover quaint neighborhoods and suburban living, all while enjoying the nearby waterways and wildlife. With its great location, Dorchester County serves as a gateway to nearby counties, making it an excellent base for your vacation. Experience the warmth and hospitality of this beautiful region as you create unforgettable memories.

  • Cambridge: Nestled in the heart of Dorchester County, Cambridge is a charming city known for its inviting outdoor spaces and family-friendly atmosphere. Visitors can enjoy a stroll along the picturesque boardwalk or relax in the local recreational areas. Shopping enthusiasts will find delightful boutiques and stores in the city center. Notable attractions include nearby beaches and the scenic esplanade, making it an ideal spot for a fun-filled day in the sun.
  • Fishing Creek: This peaceful city offers a unique blend of outdoor adventure and stunning scenery. Fishing Creek is perfect for thrill-seekers and nature lovers alike. Engage in exhilarating motor racing or explore the local recreational areas that celebrate the great outdoors. The area is also home to beautiful beaches and a nearby island, making it a fantastic destination for those looking to escape into nature or enjoy some high-speed excitement at the local racetrack.
  • Vienna: A hidden gem in Dorchester County, Vienna is a quaint city that emphasizes outdoor exploration and family experiences. Visitors can immerse themselves in educational activities while enjoying the natural beauty of the area. The boardwalk and recreational spaces provide great opportunities for family fun. Nearby attractions include pristine beaches, a scenic island, and the stunning national park, ensuring that there’s something for everyone in this delightful city.

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next adventure? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo rental that fits your budget, utilize our handy filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for planning your trips. You can start new adventures, continue from where you last paused, or review and organize your travel plans. Your saved or booked properties will be neatly categorized into Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Dorchester County getaway

Experience the unique character of Dorchester County with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Dorchester County

Are you looking for things to do in the area? Venture out of your cozy vacation rental and check out everything that makes Dorchester County a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Layton's Chance Vineyard and Winery (10.7 mi / 17.2 km)
  • St. Michaels Winery (16.5 mi / 26.5 km)
  • Phillips Wharf Environmental Center (17 mi / 27.3 km)
  • Chesapeake Beach Water Park (26.2 mi / 42.1 km)
  • Running Hare Vineyard (29.8 mi / 48 km)
  • Easton Cycle and Sport (14.2 mi / 22.9 km)

Exploring the natural landscape of Dorchester County

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Dorchester County is a great place to get out in nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Long Wharf Park (0.3 mi / 0.6 km)
  • Gerry Boyle Park at Great Marsh (0.9 mi / 1.4 km)
  • Blackwater National Wildlife Refuge (10.6 mi / 17.1 km)
  • Cove Point Park (22.6 mi / 36.4 km)
  • Matoaka Beach (22.9 mi / 36.8 km)
  • Breezy Point Beach (23.9 mi / 38.4 km)

Transportation options to and around Dorchester County

If you prefer train travel, the main station is Cambridge Station.

Frequently asked questions

What is the best area to stay in Dorchester County when booking a vacation rental?
East New Market is one of the most popular neighborhoods to get a Vrbo vacation rental in Dorchester County. Consider our collection of relaxing properties and then go out and experience the best of this destination.
What is the most popular type of vacation rental accommodation in Dorchester County?
According to our data, cottages are the most desirable type of vacation rental in Dorchester County. But that goes without saying, everyone's idea of an epic stay can vary. Vrbo has vacation rentals in a variety of sizes and shapes, so you're sure to discover the perfect fit for you.
How much does it cost to rent a vacation rental in Dorchester County?
The average price for a vacation rental in Dorchester County is determined by a number of factors, such as property type, length of stay and season. Whether you're thinking about a sprawling villa with lots of bedrooms or an apartment just enough for two, just enter your dates of travel to discover some great-value stays.
How much does it cost to rent a beach house in Dorchester County?
Prices for beach houses in Dorchester County will vary depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to refine your search results by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Dorchester County?
Pack a travel bag and a bone for your puppy dog because Dorchester County has 39 properties that welcome pets with open arms. Let your happy hound enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
Are there large group vacation rentals in Dorchester County?
With 60 vacation rentals that can sleep 10 or more guests in Dorchester County, there's no need to hold back on your invites. From fun family vacations to events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.
Are there one-bedroom vacation rentals in Dorchester County?
Yes, you'll find 18 one-bedroom properties in Dorchester County to pick from. A one-bedroom vacation rental is an excellent option if it's just you and your other half or if you're traveling solo. Throw in more space, privacy and convenience compared to a regular hotel, and you've got yourself a memorable trip.
Can I find two-bedroom vacation rentals in Dorchester County?
Dorchester County has 10 two-bedroom vacation properties to pick from. Discover a vacation home with all the comfort and privacy you're looking for at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in Dorchester County?
Whether you want to keep up with the latest news, check emails or surf social media, there are 76 vacation homes with WiFi in Dorchester County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Dorchester County?
You'll have your pick of 115 vacation homes with air conditioning in Dorchester County offering that cool, cool breeze and extra level of comfort. Enter your travel dates and then take advantage of our filter tool to help you locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Dorchester County?
Age restrictions can vary across properties on Vrbo, so look at the rules of the vacation home in Dorchester County you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Dorchester County for?
How long you can book a vacation rental in Dorchester County varies according to the property. Just enter your selected travel dates to see a list of options offering extended stays. With tons of creature comforts like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Dorchester County.
Does Vrbo offer discounts for vacation homes in Dorchester County?
Whether you're after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous bargains and discounts on Vrbo. From weekend retreats to extended vacations, we've got you covered for your next Dorchester County escape.

More Vacation Ideas