Cobb Island Vacation Rentals

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Our top choices for Cobb Island vacation rentals

Cheery, Peaceful Water Front Cabin on Winery Grounds

Cheery, Peaceful Water Front Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (58 reviews)
"Very quiet and great location."
United States
Cindy B.
$237 nightly
The price is $258
Feb 22 - Feb 23
Total with taxes and fees
Cheery, Peaceful Water Front Cabin on Winery Grounds

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.2 out of 10, Wonderful, (10 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
$282 nightly
The price is $314
Feb 22 - Feb 23
Total with taxes and fees
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (9 reviews)
"Stay was wonderful!"
United States
Karen H.
$286 nightly
The price is $290
Feb 22 - Feb 23
Total with taxes and fees
Sail Away

Easthaven: Game-Theme Waterfront Retreat+Fireplace

Easthaven: Game-Theme Waterfront Retreat+Fireplace
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
$415 nightly
The price is $452
Feb 22 - Feb 23
Total with taxes and fees
Easthaven: Game-Theme Waterfront Retreat+Fireplace

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
$300 nightly
The price is $317
Feb 21 - Feb 22
Total with taxes and fees
Cottage Located on the Patuxent River!

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic amenities, beautiful view, cosy yet spacious!"
United States
Aaron M.
$479 nightly
The price is $521
Feb 22 - Feb 23
Total with taxes and fees
River Refresh - Waterfront with Spa on Placid Bay

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
$344 nightly
The price is $375
Feb 21 - Feb 22
Total with taxes and fees
Coles Point Marina

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
$429 nightly
The price is $467
Feb 22 - Feb 23
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
$586 nightly
The price is $617
Mar 10 - Mar 11
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (14 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
$439 nightly
The price is $478
Feb 23 - Feb 24
Total with taxes and fees
Luxury Modern Waterfront Retreat

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$272 nightly
The price is $296
Feb 21 - Feb 22
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
Colonial Beach
9.8 out of 10, Exceptional, (15 reviews)
"We love going to Colonial Beach. This house offered everything we were looking for in a mini vacation."
United States
Anonymous traveler
$353 nightly
The price is $393
Feb 21 - Feb 22
Total with taxes and fees
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
$384 nightly
The price is $424
Feb 23 - Feb 24
Total with taxes and fees
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD
King George
$172 nightly
The price is $189
Mar 2 - Mar 3
Total with taxes and fees
Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

4-bedroom house in wonderful Colonial Beach

4-bedroom house in wonderful Colonial Beach
Colonial Beach
$506 nightly
The price is $563
Mar 2 - Mar 3
Total with taxes and fees
4-bedroom house in wonderful Colonial Beach

Come relax yourself a while

Come relax yourself a while
Mechanicsville
$532 nightly
The price is $587
Feb 23 - Feb 24
Total with taxes and fees
Come relax yourself a while

Sail Away To

Sail Away To
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"Perfect location and perfect property! The condo was great for our anniversary! The furnishings and amenities were top notch! We would go back again 100%. Recommend renting a golf cart. All of the places to eat are locally owned supporting small business in this community is a great feeling! The owner was so great to communicate with, so very helpful! "
United States
Katherine C.
$286 nightly
The price is $290
Feb 22 - Feb 23
Total with taxes and fees
Sail Away To
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Cobb Island Hotel Reviews

Find out more about Cobb Island

Everything you need to know about Cobb Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cobb Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cobb Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cobb Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cobb Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cobb Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $258 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cobb Island rentals

At Expedia, we put the best Cobb Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cobb Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cobb Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cobb Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Cobb Island?

Yes, we offer vacation rentals close to popular points of interest in Cobb Island, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Cobb Island?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : This vacation home rental outside of Cobb Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and an arcade game room so you can immerse yourself in your vacation.

How many vacation rentals are there in Cobb Island?

Expedia has 5 vacation rentals for your stay in Cobb Island.

What’s there to see and do in Cobb Island?

While you're exploring the area, Colonial Beach and Westmoreland State Park are a couple of picturesque spots to get outside and enjoy nature. Colonial Beach Historical Society and George Washington Birthplace National Monument are a couple of places you'll find in the larger area.

What’s a vacation rental in Cobb Island like?

A vacation rental is a private property where you can stay for a couple of days or more in Cobb Island. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for small groups.