Cobb Island vacation rentals

We found 128 vacation rentals — enter your dates for availability

Escape to the enchanting charm of Cobb Island, where lush parks and pristine beaches invite adventure and relaxation alike. This idyllic destination boasts a friendly atmosphere perfect for families and groups, offering cozy accommodations ranging from seaside apartments to charming cottages. Explore nearby attractions like Westmoreland State Park and Colonial Beach, where rich history and vibrant culture await. A vacation rental here provides the comfort and space of home, ensuring unforgettable memories for everyone.

Holiday rentals with weekly discounts - Cobb Island

Showing deals for:Dec 25 - Jan 1

A view of the livingroom from the kitchen.
Every guest says, "Bigger than it looks"..2200 square feet on one level!
Great kitchen with views of the river and easy access to outside grill
Dining area
Exceptional
(90 reviews)

Great River Views, walk to Beach !

Colonial Beach

8% off
$361
$2,526 for 7 nights
All fees included
Great River Views, walk to Beach !
Exterior
Living area
Outdoor dining
Interior
Exceptional
(22 reviews)

Bayview Breeze w/screened porch

Colonial Beach

9% off
$366
$2,564 for 7 nights
All fees included
Bayview Breeze w/screened porch
Exterior
Property grounds
Room
Dining
Exceptional
(25 reviews)

Breton Bay Family Getaway

Leonardtown

11% off
$597
$4,178 for 7 nights
All fees included
Breton Bay Family Getaway
Comfortable Family Dining
Warm and Homey with Beautiful River Front Views
Adorable waterfront cottage with spacious yard
Waterfront Horizons
Exceptional
(30 reviews)

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Cobb Island

9% off
$366
$2,565 for 7 nights
All fees included
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Private kitchen
Property grounds
Room
Interior
Wonderful
(8 reviews)

Windswept Getaway

Newburg

9% off
$295
$2,063 for 7 nights
All fees included
Windswept Getaway
Interior
Exterior
Room
Dining
Exceptional
(37 reviews)

Cottage on The Point! Bring your bikes & golf cart, and your pets!

Colonial Beach

9% off
$202
$1,414 for 7 nights
All fees included
Cottage on The Point! Bring your bikes & golf cart, and your pets!
Private kitchen
Property grounds
Exterior
Room
Wonderful
(6 reviews)

Cabernet Cottage on Water at Monroe Bay Winery, tiny container cottage

Colonial Beach

9% off
$127
$890 for 7 nights
All fees included
Cabernet Cottage on Water at Monroe Bay Winery, tiny container cottage

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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)
  • Budds Creek Motocross Park (10.1 mi / 16.2 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)

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:

  • 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)
  • Chapel Point State Park (17.4 mi / 28.1 km)
  • Rappahannock River Valley National Wildlife Refuge (18.3 mi / 29.4 km)
  • St. Clement's Island State Park (6.1 mi / 9.8 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.
What are the most popular vacation rentals in Cobb Island?
The most popular vacation rentals in Cobb Island are houses and cottages. These property types make up the majority of available options, offering guests ample space, privacy, and a comfortable base for their stay. Guests often choose these for their ability to accommodate families and groups, providing a true home-away-from-home experience with room to relax and enjoy the island's tranquil atmosphere.
What amenities do vacation rentals in Cobb Island usually offer?
Vacation rentals in Cobb Island typically offer a range of amenities designed for a comfortable stay. You'll often find fully equipped kitchens, laundry facilities, and convenient parking. Many properties also include high-speed internet access, air conditioning, and televisions for entertainment. Guests can also enjoy outdoor areas, with some rentals featuring balconies, patios, or yards for relaxing outside.
Are there family-friendly vacation rentals in Cobb Island?
Yes, vacation rentals in Cobb Island offer around 5 family-friendly options, primarily consisting of houses and cottages. These properties provide the space and amenities families need for a comfortable trip. You'll often find features like fully equipped kitchens for meal preparation, laundry facilities, and outdoor play areas. Many also include games and barbecue grills, perfect for family gatherings and creating lasting memories.
Are there pet-friendly vacation rentals in Cobb Island?
Yes, a selection of pet-friendly vacation rentals is available in Cobb Island, with houses being the primary property type. These rentals understand the importance of traveling with your furry companions. You can expect amenities such as a yard, providing a convenient outdoor space for pets to enjoy during your stay.
What are the best areas for group vacation rentals in Cobb Island?
Cobb Island offers several vacation rentals well-suited for groups, with a few properties designed to accommodate larger parties. These are predominantly houses and cottages, providing ample space for everyone to gather and relax. You'll find amenities like fully equipped kitchens for shared meals, multiple bedrooms and bathrooms, and spacious outdoor areas perfect for socializing and enjoying the island's atmosphere.
What are the best luxury vacation rentals in Cobb Island?
Cobb Island features a selection of several luxury vacation rentals, primarily houses, offering an elevated stay experience. These upscale properties often come with premium amenities designed for comfort and indulgence. You might find features such as private pools, hot tubs, and jetted bathtubs for ultimate relaxation. Many also boast scenic views and private outdoor spaces like balconies or terraces, perfect for enjoying the tranquil surroundings.
Are there any budget-friendly vacation rentals in Cobb Island?
Yes, Cobb Island offers a selection of several budget-friendly vacation rentals, with cottages and some houses providing great value. These properties are ideal for guests looking for an affordable yet comfortable stay. You'll often find essential amenities like fully equipped kitchens, laundry facilities, and free parking, which can help reduce overall trip costs. Choosing a rental with these features allows you to save on dining out and other expenses, making your vacation more economical.
Are there any vacation rentals in Cobb Island with a hot tub?
Yes, a selection of vacation rentals in Cobb Island offers hot tubs, typically found in houses. These properties provide a relaxing amenity for guests to unwind after a day of exploring. You might find hot tubs integrated with jetted bathtubs, offering a soothing experience during your stay.
Are there any short-term vacation rentals in Cobb Island for a weekend getaway?
Yes, vacation rentals in Cobb Island are well-suited for weekend getaways, offering a selection of houses and cottages. These properties provide a comfortable and private base for a two or three-night trip. You can easily settle in and enjoy the island's scenic beauty, local seafood restaurants, and nearby attractions, making it a perfect destination for a quick escape.
Are there any remote work vacation rentals in Cobb Island?
Yes, vacation rentals in Cobb Island offer options for remote work, with several properties available for longer stays. These rentals often include essential amenities like high-speed internet, fully equipped kitchens, and laundry facilities, providing a comfortable setting for productivity. Choosing a house or cottage allows for a dedicated space to work while enjoying the tranquil island environment.
How much does a Cobb Island vacation rental cost?
A vacation rental in Cobb Island typically costs an average of $492 per night, with prices starting from around $410 per night. The cost can vary based on the property type, with cottages sometimes offering more budget-friendly options compared to larger houses. Prices also tend to be higher during the peak season from May to July, especially in June, and may offer better value during the quietest season from October to December.
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.

More Vacation Ideas