Cobb Island vacation rentals

We found 135 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Cobb Island that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for spending time at your vacation home, which might include a garden and WiFi. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Find out more about Cobb Island

Find out more about Cobb Island

Why visit Cobb Island

  1. Outdoor Adventures: Enjoy various activities like bird watching and ocean trips, perfect for nature lovers.
  2. Romantic Getaway: Cobb Island offers a tranquil setting ideal for couples looking to unwind together.
  3. Cultural Events: Participate in local festivities like the Cobb Island Day Festival to experience community spirit.
  4. Scenic Shores: Relax on beautiful beaches and explore the stunning natural beauty of the island.
  5. Charming Accommodations: Choose from cozy cottages and vacation homes for a comfortable stay.

Popular types of accommodation in Cobb Island

Planning a getaway to Cobb Island? Start by exploring the top accommodation options for your stay, including houses, charming cottages, and comfortable apartments. Whether you're searching for cobb island hotels, a relaxing resort, or simply checking hotel availability, we've got you covered. Enjoy the beauty of the island while finding the perfect place to call home during your visit!

  • Houses: The top choice for visitors to Cobb Island, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option that provides a cozy and inviting atmosphere, perfect for a peaceful getaway.
  • Apartments: A convenient choice for guests seeking a self-contained living space with essential amenities.
  • Cabins: These rustic retreats are perfect for those who appreciate nature and a serene environment.
  • Condos: A modern and stylish option, great for travellers wanting a bit of luxury during their stay.**

Top attractions in Cobb Island

Cobb Island, Maryland, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore local attractions like national and state parks, marinas, and urban parks, ideal for family and cultural experiences. Don't miss the chance to enjoy bird watching, participate in the Cobb Island Day Festival, take a guided tour of Cobb Island, or embark on an exciting ocean trip. This charming destination offers a variety of activities to create unforgettable memories.

  1. Westmoreland State Park: Nestled 11.3km from Cobb Island, this national park offers breathtaking scenery, diverse wildlife, and numerous outdoor activities like hiking and kayaking, making it perfect for adventure seekers.
  2. Colonial Beach: Located 9.7km away, this charming town boasts a vibrant atmosphere with quaint shops, dining options, and a lovely waterfront, ideal for those looking to soak in local culture.
  3. Bayside Marina: Just 11.3km from Cobb Island, this marina features stunning beach views and opportunities for boating and fishing, catering to outdoor enthusiasts and adventure lovers alike.

Things to do recommended for couples

For a romantic getaway in Cobb Island, explore nearby wineries like Ingleside Vineyards and Port of Leonardtown Winery, both 17.7km away, offering enchanting atmospheres. Don't miss Hague Winery, located 19.7km away, providing delightful experiences perfect for couples seeking memorable moments together.

Things to do recommended for groups

Experience the thrill of motor racing at Maryland International Raceway, just 16.1km away, or enjoy a round of golf at Cameron Hills Golf Links, located 24.1km from Cobb Island. Don't forget to explore Cecil's Old Mill, a charming store 30.6km away for unique finds.

What do I need to keep in mind when booking a vacation in Cobb Island

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cobb Island with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Cobb Island with young kids: Travelling with young children can be a bit demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Cobb Island: For many families, a trip isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Cobb Island: If you're in search of vacation rentals offering discounts for stays of a month or more, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Cobb Island

Cobb Island, Maryland, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Explore the tranquil beauty of this small island, where friendly locals create a welcoming atmosphere. Nearby, discover the allure of Little Cobb Island and enjoy family-friendly activities. Whether you're relaxing on the scenic shores or delving into the area's rich history, Cobb Island promises an unforgettable vacation experience filled with natural beauty and a sense of community.

  • Colonial Beach: Located 11.3km from Cobb Island, Colonial Beach is a delightful waterfront city known for its stunning outdoor experiences and romantic ambiance. The vibrant boardwalk invites visitors for leisurely strolls while enjoying picturesque views of the Potomac River. Families will appreciate the recreational areas and the inviting family beach, perfect for sunbathing and swimming. For thrill-seekers, the local motor racing events offer an exhilarating experience. Colonial Beach is an ideal spot for those seeking a blend of relaxation and adventure amidst scenic surroundings.
  • Leonardtown: Situated 19.3km from Cobb Island, Leonardtown is a charming city rich in scenic beauty and outdoor adventure. Visitors can explore its recreational areas, which provide ample opportunities for hiking and nature walks. The city's proximity to the national state park enhances the outdoor experience, offering trails and breathtaking views. Leonardtown’s vibrant community also features educational venues that celebrate local history and culture, making it a great destination for those looking to expand their knowledge while enjoying the great outdoors. The nearby beaches and lakes provide additional opportunities for relaxation and exploration.
  • Avenue: Just 6.4km from Cobb Island, Avenue is a quaint city that offers a perfect escape for outdoor enthusiasts and couples seeking romance. The area is known for its scenic landscapes, with beautiful beaches and a serene lake that invite visitors to unwind. The recreational areas are perfect for picnicking and leisurely activities, while motor racing events add a thrilling dimension to your visit. Avenue also boasts educational attractions, providing insights into the local culture and history, making it a well-rounded destination for all types of travellers.

Best time to go to Cobb Island

If you're planning a trip to Cobb Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
February39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low
March46.2°F (7.9°C)Light RainMostly SunnyAverageSlightly Low
April56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
May65.5°F (18.6°C)Light RainMostly SunnyAverageAverage
June73.8°F (23.2°C)Light RainMostly SunnyModerately HighSlightly High
July78.6°F (25.9°C)Light RainMostly SunnyModerately HighSlightly High
August76.5°F (24.7°C)Light RainMostly SunnyModerately HighSlightly High
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October59.9°F (15.5°C)Light RainMostly SunnyModerately LowAverage
November48.2°F (9.0°C)Light RainMostly SunnyModerately LowAverage
December41.5°F (5.3°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming trip? Being flexible with your travel dates can help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for you to plan your trips, resume your previous work, or manage your travel arrangements. Here, you can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Cobb Island getaway

Experience the unique character of Cobb Island with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Cobb Island

Are you searching for attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Cobb Island a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Maryland International Raceway (9.9 mi / 15.9 km)
  • Ingleside Vineyards (11.4 mi / 18.4 km)
  • Ingleside Vineyards (11.7 mi / 18.9 km)
  • Caledon State Park (17.8 mi / 28.6 km)
  • Wicomico Shores Golf Course (8.6 mi / 13.9 km)
  • Breton Bay Golf Course (9.5 mi / 15.4 km)

Exploring the natural landscape of Cobb Island

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

  • St. Clement's Island State Park (6.1 mi / 9.8 km)
  • Colonial Beach (6.4 mi / 10.2 km)
  • Westmoreland State Park (7.4 mi / 11.8 km)
  • St. Mary's River State Park (15.9 mi / 25.6 km)
  • Rappahannock River Valley National Wildlife Refuge (18.3 mi / 29.4 km)
  • Cooksey Island (9.5 mi / 15.3 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Cobb Island?
Houses are the most popular kind of vacation rental in Cobb Island, according to our data. Even if you have something different in mind, Vrbo has vacation homes in many shapes and sizes. Explore our options to find your perfect Cobb Island pad.
How much does it cost to rent a vacation rental in Cobb Island?
Property type, length of stay and time of year are some factors that can affect the price of a vacation home. Simply enter your dates of travel to find your ideal escape. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Cobb Island?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside escape. Enter your Cobb Island travel dates to view your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you need.
What are popular rental amenities in Cobb Island?
When it comes to rental amenities that guests are on the lookout for in Cobb Island, a nearby river, a nearby waterfront and a barbecue grill are at the top of the list. With Vrbo vacation homes, you’ll discover options to suit your style and taste, whether you’re going on a vacation with relatives, friends or even pets.
What are the top attractions for families in Cobb Island?
Give the kiddos a good time at these exciting family-friendly attractions in Cobb Island:

  • St. Clements Island State Park
  • New Towne Neck State Park

Are there vacation rentals with WiFi in Cobb Island?
Cobb Island has two vacation rentals with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to scrolling social media, these Vrbo homes make it easy to get online.
How old do you have to be to rent a vacation rental in Cobb Island?
You’ll need to check with the Cobb Island vacation property you’re considering on Vrbo as the age limit differs. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Cobb Island for?
The amount of time you can rent a Cobb Island vacation rental for varies depending on the property. Just put in your travel dates to find options that offer long-term stays. They include everything you need to make your extended vacation more convenient and enjoyable, such as kitchens and backyards. Some Vrbo vacation homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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