Cobb Island vacation rentals

We found 126 vacation rentals — enter your dates for availability

Discover a selection of 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.

Holiday rentals with weekly discounts - Cobb Island

Showing deals for:Aug 28 - Sep 4

Image gallery for Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Property grounds
9.8 out of 10, Exceptional, (155 reviews)
Exceptional
(155 reviews)

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Newburg

9% off
Price is $208
$1,457 for 7 nights
All fees included
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

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Find out more about Cobb Island

Why visit Cobb Island

  • Outdoor Adventures: Cobb Island is perfect for nature lovers, offering national and state parks for hiking, fishing, and exploring.
  • Charming Atmosphere: Experience the quaint, friendly vibe of the island, ideal for relaxation and family-friendly activities.
  • Beautiful Beaches: Enjoy summer fun on the sandy shores, perfect for lounging and soaking up the sun.
  • Cozy Accommodations: Choose from private homes, cottages, and seaside apartments for a comfortable stay.
  • Rich Local Culture: Explore the historical charm of nearby regions, adding depth to your vacation experience.

Popular types of accommodation in Cobb Island

Planning a getaway to Cobb Island? You're in for a treat. This charming destination offers a variety of vacation rentals, including houses, cozy cottages, and seaside apartments. Enjoy the convenience of laundry facilities and explore the best of Maryland with our selection of beach house and cottage rentals. Start your adventure by finding the perfect place to stay on your Cobb Island retreat.

  • Houses: The top choice for travelers in Cobb Island, offering spacious accommodations perfect for families or groups.
  • Cottages: These charming retreats provide a cozy atmosphere, ideal for a relaxing getaway by the water.
  • Apartments: Conveniently located, these rentals offer the comforts of home and easy access to local attractions.
  • Cabins: A popular option for nature lovers, these rustic spots blend comfort with the great outdoors.
  • Villas: Luxurious and spacious, villas provide a high-end experience for those seeking elegance and comfort.**

Top attractions near Cobb Island

Cobb Island, Maryland, is an ideal destination for outdoor enthusiasts and beach lovers. Visitors can explore a variety of attractions, including national and state parks, marinas, and urban parks. Whether you're seeking family-friendly activities or cultural experiences, Cobb Island offers numerous opportunities to enjoy its beautiful scenery and outdoor adventures, making it a perfect getaway for travelers looking to relax and connect with nature.

  • Westmoreland State Park: Nestled 7 miles from Cobb Island, this park boasts stunning scenery and outdoor adventures. Enjoy hiking trails, picnicking, and breathtaking views of the Potomac River, making it perfect for nature lovers.
  • Colonial Beach: Located 6 miles away, this charming town features a lively atmosphere with beautiful beaches, shops, and restaurants, offering a perfect blend of relaxation and local culture.
  • George Washington Birthplace National Monument: Just 7 miles from Cobb Island, this museum celebrates the life of the first president with historical exhibits and scenic landscapes, immersing visitors in American heritage.

Things to do recommended for couples

For a romantic getaway in Cobb Island, enjoy a sunset stroll along the waterfront, savoring fresh seafood at local eateries. Explore the serene beauty of the island by renting a kayak or simply relax on the beach, soaking in the tranquil atmosphere together.

Things to do recommended for families

Families visiting Cobb Island can enjoy kayaking on the Potomac River, exploring nature trails at the nearby parks, and indulging in fresh seafood at local eateries. Don't miss the chance to see stunning sunsets along the beach, making it a memorable family getaway.

Things to do recommended for groups

Groups visiting Cobb Island can enjoy fishing excursions on the Potomac River, savor local seafood at charming waterfront restaurants, and explore the scenic beauty of nearby parks. Don’t miss the opportunity for a group kayaking adventure to experience the tranquility of the island's surroundings.

*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 Cobb Island

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • 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. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Cobb Island with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Cobb Island: For many families, a vacation isn’t truly enjoyable without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer amenities like food 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 with special offers 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Cobb Island

Cobb Island, Maryland, offers a delightful escape for those seeking beach vibes and a charming town atmosphere. With its serene outdoor spaces and friendly locals, this picturesque island is perfect for summer fun. Explore nearby regions that boast historical charm and family-friendly activities, making it an ideal destination for relaxation and adventure. Whether you're lounging on the beach or strolling through quaint neighborhoods, Cobb Island promises a memorable vacation experience.

  • Colonial Beach: Located 7 miles from Cobb Island, Colonial Beach is a charming city that offers a delightful blend of outdoor activities and scenic views. Travelers are drawn to its beautiful boardwalk and recreational areas, making it the perfect spot for a romantic getaway. Highlights include the picturesque beach and serene lake, which provide ample opportunities for relaxation and family fun. For those seeking adventure, motor racing events add an exciting twist to your visit, making Colonial Beach a must-see destination.
  • Avenue: Just 4 miles from Cobb Island, Avenue is a quaint city that captivates visitors with its stunning scenery and beach experiences. This area is perfect for outdoor enthusiasts, with access to the beautiful bay and river nearby. Travelers can indulge in recreational activities or take part in educational experiences while enjoying the coastal landscape. Avenue's inviting atmosphere, coupled with its local beaches, makes it an ideal spot for a peaceful day in nature, complete with picturesque views and fun-filled adventures.
  • Bushwood: Also located 4 miles from Cobb Island, Bushwood is a vibrant city known for its outdoor experiences and sporting events. Visitors can explore the local recreational areas and enjoy shopping at nearby centers. The attractive river and lake provide great spots for both relaxation and activities, while urban parks offer a perfect setting for picnics and leisurely strolls. Bushwood is an excellent destination for those who appreciate a blend of sports and natural beauty, ensuring a memorable vacation experience.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Moreover, extending your stay can lead to fantastic savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We’re here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can easily create new trips, continue planning from where you last stopped, or manage your travel arrangements. You'll find your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/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)
  • Wicomico Shores Golf Course (8.6 mi / 13.9 km)
  • Breton Bay Golf Course (9.5 mi / 15.4 km)
  • Port of Leonardtown Winery (10.6 mi / 17.1 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)
  • Rappahannock River Valley National Wildlife Refuge (18.3 mi / 29.4 km)
  • Cedar Island (10.8 mi / 17.4 km)
  • St. Mary's River State Park (15.9 mi / 25.6 km)

Frequently asked questions

What is the best area to stay in Cobb Island, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Cobb Island, Maryland, the area surrounding the island itself is a fantastic choice. This charming locale is known for its serene waterfront views and a close-knit community atmosphere. One of the highlights of staying here is the opportunity to explore the nearby rivers, where fishing and boating are popular activities.

Additionally, the island offers beautiful parks and nature walks, superb for those who enjoy the outdoors. Nearby, you can visit places like the historic St. Clements Island State Park, which is not only a scenic spot for picnics and hiking but also holds significant historical value as the site of Maryland's first settlement.

While the exact number of properties may vary, Cobb Island features a selection of cozy vacation rentals that cater to different tastes and budgets. This makes it easy for visitors to find a comfortable place to stay while enjoying the tranquil charm and natural beauty of the area.
How much does it cost to rent a vacation home in Cobb Island?
Prices for vacation rentals in Cobb Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cobb Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cobb Island vacation house rentals?
You can find great discounts on house rentals in Cobb Island on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Cobb Island?
In Cobb Island, vacation houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties typically feature spacious layouts, with multiple bedrooms and well-equipped kitchens, providing a comfortable home-like atmosphere for families and groups. Many rentals also offer outdoor spaces, such as decks or patios, where guests can relax and enjoy the serene waterfront views.
Are there any family house rentals in Cobb Island?
In Cobb Island, Maryland, there are several family-friendly house rentals available, great for a memorable getaway. This quaint island offers a peaceful atmosphere and a close-knit community feel, making it an ideal spot for families. Many of the properties feature spacious living areas, full kitchens for preparing family meals, and outdoor decks or yards where children can play and enjoy the fresh air.

Located near the water, many homes provide easy access to fishing, kayaking, and other water activities, ideal for families looking to bond over outdoor adventures. Visitors can also explore nearby attractions, such as local parks and scenic waterfront views, ensuring that there's something for everyone.
Can I find long-stay vacation rentals in Cobb Island?
A long-stay vacation rental in Cobb Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Cobb Island?
In Cobb Island, travelers can find several pet-friendly house rentals that cater to those looking to enjoy a waterfront getaway with their furry companions. Many of these rentals come equipped with essential amenities such as fully stocked kitchens, outdoor spaces for relaxation, and comfortable living areas that make for a cozy stay.

The island itself offers a tranquil atmosphere, great for those seeking a peaceful retreat. Nearby points of interest include scenic views of the Potomac River, where you can enjoy fishing or kayaking, providing great opportunities for outdoor activities with pets. While exploring Cobb Island, visitors can also find pet-friendly cafes and parks that welcome four-legged friends, ensuring that both guests and their pets can enjoy the beautiful surroundings together.
Are there any remote work vacation rentals in Cobb Island?
In Cobb Island, Maryland, there are several vacation rentals available that cater to remote work needs. Many of these properties offer essential amenities such as free Wi-Fi and internet services, ensuring that guests can stay connected while enjoying the serene surroundings. You can expect comfortable living spaces equipped with dedicated work areas, making it easy to balance work and relaxation.

Additionally, many rentals in Cobb Island provide a peaceful environment, ideal for focus, and often feature outdoor spaces where you can unwind after a productive day. The charming waterfront views and tranquil atmosphere further enhance the experience, making it a great choice for those looking to work remotely while enjoying a getaway. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cobb Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cobb Island with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cobb Island?
In Cobb Island, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the views. Additional amenities that are commonly found include dining areas for family meals, blenders for smoothies or morning coffee, and onsite parking for convenience.
When is the best time to visit Cobb Island for a vacation rental?
The most popular time to visit Cobb Island is during the vibrant summer months of June through August, when travelers flock to this charming destination for its warm weather and outdoor activities. July stands out as the peak month, offering ideal conditions for beach outings, fishing, and enjoying the laid-back island lifestyle alongside fellow vacationers.

During this season, you can expect pleasant temperatures ranging from the mid-70s to low 90s Fahrenheit, creating a comfortable environment for water sports and sunbathing. The island's picturesque surroundings provide ample opportunities for sightseeing, including beautiful waterfront views and local dining experiences that highlight the region's seafood.

For those seeking a more budget-friendly option, consider planning your visit in November. This month offers a unique charm as the crowds diminish, allowing for peaceful exploration of the island's natural beauty and a chance to enjoy local attractions without the bustling summer atmosphere.

Ultimately, the best time to book a vacation rental in Cobb Island depends on your preference for lively summer activities or a more tranquil retreat in the off-peak season.
How early should I book a Cobb Island vacation rental?
Book your Cobb Island vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cobb Island, Maryland, United States of America?
Cobb Island, Maryland, offers a unique blend of natural beauty and outdoor activities. One of the main attractions is the serene waterfront, which is great for fishing, kayaking, and boating, allowing visitors to enjoy the scenic views of the Potomac River. The island itself is relatively small and features charming residential areas, making it a peaceful retreat for those looking to escape the hustle and bustle of city life.

Nearby, the Cobb Island Marina is a great spot for both locals and visitors to engage in water activities or simply relax by the dock. The island's proximity to the larger St. Mary's County also provides access to additional attractions, such as historic sites and nature reserves. Travelers can explore the nearby Point Lookout State Park, which offers hiking trails and birdwatching opportunities, as well as a glimpse into Civil War history.
Can I change or cancel my Cobb Island home rental booking on Vrbo?
To find Cobb Island vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cobb Island vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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