Cobb Island holiday homes

We found 128 holiday rentals — enter your dates for availability
Discover a selection of 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:18 Dec - 25 Dec

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

Great River Views, walk to Beach !

Colonial Beach

8% off
NZ$4,865
for 7 nights, 1 home
NZ$695 per night
includes taxes & fees
Great River Views, walk to Beach !
Interior
Living area
Exterior
Outdoor dining
Exceptional
(22 reviews)

Bayview Breeze w/screened porch

Colonial Beach

8% off
NZ$5,010
for 7 nights, 1 home
NZ$716 per night
includes taxes & fees
Bayview Breeze w/screened porch
Interior
Property grounds
Room
Exterior
Exceptional
(25 reviews)

Breton Bay Family Getaway

Leonardtown

10% off
NZ$7,766
for 7 nights, 1 home
NZ$1,109 per night
includes taxes & fees
Breton Bay Family Getaway
Living area
Interior
Exterior
Living area
Exceptional
(37 reviews)

Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly

Colonial Beach

8% off
NZ$3,279
for 7 nights, 1 home
NZ$468 per night
includes taxes & fees
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
Adorable waterfront cottage with spacious yard
Warm and Homey with Beautiful River Front Views
Open concept kitchen
Waterfront Horizons
Exceptional
(29 reviews)

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Cobb Island

8% off
NZ$4,711
for 7 nights, 1 home
NZ$673 per night
includes taxes & fees
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Room
Exterior
Dining
Property grounds
Exceptional
(37 reviews)

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

Colonial Beach

8% off
NZ$2,640
for 7 nights, 1 home
NZ$377 per night
includes taxes & fees
Cottage on The Point! Bring your bikes & golf cart, and your pets!
Interior
Property grounds
Dining
Private kitchen
Wonderful
(8 reviews)

Windswept Getaway

Newburg

9% off
NZ$3,758
for 7 nights, 1 cottage
NZ$537 per night
includes taxes & fees
Windswept Getaway
Kitchen and Dining Area
Kitchen view of dining room & sitting area
Dining Room
Lounge chairs for catching rays
Exceptional
(99 reviews)

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach

12% off
NZ$4,530
for 7 nights, 1 home
NZ$647 per night
includes taxes & fees
Inviting and Serene Home on Monroe Bay Creek
Exterior
Property grounds
Private kitchen
Private kitchen
Wonderful
(6 reviews)

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

Colonial Beach

8% off
NZ$1,701
for 7 nights, 1 cottage
NZ$243 per night
includes taxes & fees
Cabernet Cottage on Water at Monroe Bay Winery, tiny container cottage

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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)
  • 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 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)
  • St. Mary's River State Park (15.9 mi / 25.6 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)
  • Abell's Wharf (10.8 mi / 17.3 km)

Frequently asked questions

What is the best area to stay in Cobb Island when booking a holiday rental?
Cobb Island is a charming destination offering a delightful escape for those looking to enjoy the tranquillity of the Maryland waterfront. The best area to consider for a holiday rental is the waterfront neighbourhood, where you can find a range of properties that offer stunning views of the Potomac River. This area is particularly appealing for those who relish the idea of waking up to panoramic vistas and the soothing sounds of nature.Within this neighbourhood, you'll find several lovely attractions to enhance your stay. The Cobb Island Marina is a fantastic spot for boating enthusiasts and those wanting to immerse themselves in the local fishing culture. Additionally, the nearby St. George Island offers beautiful beaches and walking trails, superb for leisurely strolls or picnics with loved ones.The number of properties available in this picturesque area varies, but you can generally expect a selection ranging from cosy cottages to spacious homes, all designed to accommodate different group sizes, ensuring a comfortable and enjoyable stay.
What is the most popular type of holiday rental accomodation in Cobb Island?
In Cobb Island, holiday houses are the most popular type of holiday rental, with around 16 available. These properties are typically spacious and well-equipped, featuring multiple bedrooms, fully stocked kitchens, and outdoor decks or patios ideal for enjoying the picturesque views of the surrounding waters. Additionally, there are several charming cottages that provide a cozier, more intimate atmosphere, superb for couples or smaller families.
Are there any family house rentals in Cobb Island?
In Cobb Island, Maryland, there are several family-friendly house rentals available, making it an excellent choice for families seeking a relaxing getaway. The area features charming homes that often come equipped with spacious living rooms, fully stocked kitchens for preparing meals together, and outdoor spaces where children can safely play. Many properties also offer amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.The island itself is a peaceful retreat, surrounded by beautiful waterways and nature, great for outdoor activities. Nearby, families can enjoy the scenic waterfront, where fishing and boating opportunities abound.
Are there pet-friendly house rentals in Cobb Island?
In Cobb Island, there are several pet-friendly house rentals available, making it an excellent choice for those wishing to bring their furry companions along. Many of these holiday homes offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.The area itself is known for its scenic waterfront views and relaxed atmosphere, superb for leisurely strolls with pets. Nearby, the Cobb Island Marina provides opportunities for boating and fishing, and there are several parks where you can take your dog for a walk or simply enjoy nature.
Are there any remote work holiday rentals in Cobb Island?
In Cobb Island, Maryland, there are around 20 remote work-friendly holiday rentals available, making it a suitable destination for those looking to balance work and relaxation. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, ensuring that you can stay connected throughout your stay. Guests can expect comfortable living spaces with dedicated work areas, making it easy to manage remote work tasks.Cobb Island's serene environment is ideal for unwinding after a day's work. The area offers picturesque views of the Chesapeake Bay, and you can often find properties with outdoor spaces where you can enjoy the fresh air. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Cobb Island?
In Cobb Island, popular rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the serene surroundings. Additionally, amenities like blenders and dining areas enhance the convenience and comfort of the accommodations. Onsite parking is another common feature, ensuring easy access for those travelling by car.
When is the best time to visit Cobb Island for a holiday rental?
The peak season for visiting Cobb Island is during the summer months of June to August, with July being particularly popular among holidaymakers seeking a relaxing getaway. During this time, visitors can relish in warm temperatures averaging around 25 to 30 degrees Celsius, superb for enjoying outdoor activities like boating, fishing, and sunbathing on the picturesque shores.The summer months bring a vibrant setting to the island, with families and friends gathering to create unforgettable memories. Cobb Island's scenic landscapes and tranquil waters provide an ideal setting for sightseeing and leisurely strolls along the waterfront.For those looking for a more budget-friendly experience, consider planning your visit in November. This quieter month offers a more relaxed pace, allowing you to explore the island's natural beauty without the crowds. You can enjoy peaceful walks along the beach and take in the serene surroundings, all while benefiting from potentially lower rental rates.Ultimately, the best time to visit Cobb Island depends on whether you prefer the lively summer vibe or the calm and tranquillity of the off-season.
What are the top attractions in Cobb Island?
Cobb Island, a quaint community located along the Potomac River, offers a peaceful retreat with its scenic waterfront views and outdoor activities. One of the main attractions is the Cobb Island Marina, which provides opportunities for boating, fishing, and enjoying the serene river scenery. The island is also known for its charming local eateries, where visitors can savour fresh seafood and experience the friendly atmosphere of the community.Nature enthusiasts will appreciate the nearby shores and marshlands, great for birdwatching and exploring the natural beauty of the area. The island's tranquil environment makes it an ideal spot for those seeking a quiet getaway, with lovely walking paths and spots to enjoy the sunset over the water.
Are all fees included in the Cobb Island holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Cobb Island holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Cobb Island holiday homes?
You can find great discounts on holiday homes in Cobb Island on Bookabach, 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.
Can I change or cancel my Cobb Island holiday home booking on Bookabach?
To find Cobb Island holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Cobb Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Cobb Island holiday home?
Book your Cobb Island holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cobb Island?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Cobb Island to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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