Cobb Island holiday lettings

We found 126 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Cobb Island that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Cobb Island

Showing deals for:6 Mar - 13 Mar

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Miscellaneous
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Windswept Getaway

Newburg, MD

8% off
Price is £1,694
for 7 nights, 1 cottage
£242 per night
includes taxes & fees
Windswept Getaway

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Cobb Island getaway

Learn about the unique charm of Cobb Island with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to discover attractions to see during your stay? Venture out of your holiday home and experience everything that makes Cobb Island a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 fun outdoor activities or just want to spend some time taking in the scenery, Cobb Island is a great place to get outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Colonial Beach (6.4 mi / 10.2 km)
  • Westmoreland State Park (7.4 mi / 11.8 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)
  • The Sands (6.1 mi / 9.9 km)

Frequently asked questions

What is the best area to stay in Cobb Island when booking a holiday rental?
When considering a holiday rental in Cobb Island, Maryland, the best area to stay is near the waterfront. This location not only offers stunning views of the Potomac River but also provides easy access to a variety of outdoor activities. The charming atmosphere of the waterfront area creates a peaceful retreat, great for those looking to unwind amidst nature.

One of the top attractions in this region is the Cobb Island Marina, where visitors can enjoy boating, fishing, and kayaking. The marina serves as a hub for water-based activities and is ideal for those who wish to explore the scenic waterways or simply relax by the shore. Additionally, the nearby St. George Island is a wonderful spot for a day trip, offering beautiful beaches and opportunities for wildlife watching.
How much does it cost to rent a holiday home in Cobb Island?
Prices for holiday 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 holiday 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 holiday rental accomodation in Cobb Island?
In Cobb Island, holiday houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties typically feature spacious layouts, offering multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the serene waterfront views. Many rentals are located in quiet neighbourhoods, making them ideal for families or groups looking to relax and enjoy the natural beauty of the island.
Are there any family house rentals in Cobb Island?
In Cobb Island, Maryland, there are several family-friendly house rentals available, ensuring that visitors have a comfortable stay. This charming locale offers spacious properties that often include amenities such as full kitchens, ideal for preparing family meals, and outdoor areas superb for children to play. Many homes feature cosy living rooms and some even provide access to private docks, which can be a delightful feature for families looking to enjoy water activities.
Can I find long-stay holiday rentals in Cobb Island?
A long-stay holiday rental in Cobb Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cobb Island?
In Cobb Island, there are several pet-friendly house rentals available that cater to those travelling with their furry companions. The island offers a serene waterfront setting, great for a relaxing getaway. Many of the holiday homes feature spacious layouts, modern kitchens, and outdoor spaces where pets can roam freely.
Are there any remote work holiday rentals in Cobb Island?
In Cobb Island, Maryland, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as Wi-Fi, desks, and desk chairs, allowing for a comfortable and productive work environment. The island itself offers a serene atmosphere, surrounded by water and natural beauty, making it an ideal location for those looking to balance work with relaxation. Additionally, the nearby waterfront provides opportunities for leisure activities, enhancing the overall experience for remote workers seeking a peaceful retreat. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cobb Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cobb Island with parking available—perfect for families or travellers 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 rental amenities include essential kitchen facilities, making it convenient for guests to prepare their own meals. Most rentals feature a fully equipped kitchen with a dishwasher, microwave, and necessary cookware, dishware, and utensils. Additionally, dining tables are commonly available, providing a comfortable space for families or groups to enjoy meals together.
When is the best time to visit Cobb Island for a holiday rental?
The best time to visit Cobb Island for a holiday rental is during the summer months, particularly in July. This vibrant period attracts travellers, all drawn to the picturesque waterfront and the array of outdoor activities available. With temperatures typically hovering in the mid-20s Celsius, it's an ideal time for beachgoers to enjoy swimming, fishing, and kayaking in the calm waters of the Chesapeake Bay.

June through August marks the peak season, where you can immerse yourself in the lively atmosphere of Cobb Island. During these months, the community is bustling with events, and the mild evenings are superb for leisurely strolls along the shore or picnics by the water. The charm of the island truly shines with locals and visitors gathering for summer festivities, making it a wonderful time to connect with others.

For those looking for a more budget-friendly option, consider visiting in November. While this is outside the main tourist season, it offers a great experience with fewer crowds and a chance to witness the island's tranquil beauty as the leaves change. You can enjoy peaceful walks along the beach and relish the serene ambiance that Cobb Island has to offer.
How early should I book a Cobb Island holiday rental?
Book your Cobb Island holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Cobb Island home rental booking on Vrbo?
To find Cobb Island holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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