Cobb Island vacation rentals

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Top-rated vacation rentals in Cobb Island

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Guest favorite

Home in Newburg

4.92 out of 5 average rating, 103 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 4.5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The one acre lot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos & a fabulous sleeping loft for the kids!

Oct 4 – 11

G$43,251 GYD per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 123 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Sep 13 – 20

G$38,040 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 192 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

May 21 – 28

G$18,544 GYD per night

Guest favorite

Cottage in Colonial Beach

4.91 out of 5 average rating, 115 reviews

Shore Cottage Getaway - Water access

Enjoy relaxing at your cozy "Shore Cottage." Two bedroom one full bath cottage sleeps 4-6 people. Owners bedroom has queen size bed and Tv. Second bedroom has a Full size mattress bunk bed. Fully equipped kitchen and back deck grillin'! Enjoy relaxing on your front porch across from Monroe Bay. Walk to your private beach on the Potomac River. Also enjoy free access to your local marina on Doctor Point, where you can kayak, boat and even fish. Minutes from the winery, restaurants and parks!

Sep 16 – 23

G$34,691 GYD per night

Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 119 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Sep 11 – 18

G$28,706 GYD per night

Guest favorite

Cabin in Colonial Beach

4.97 out of 5 average rating, 100 reviews

Spring Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Aug 5 – 12

G$30,285 GYD per night

Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 143 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Jan 22 – 29

G$18,619 GYD per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 313 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Mar 22 – 29

G$18,368 GYD per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 536 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Nov 7 – 14

G$29,825 GYD per night

Superhost

Home in Colonial Beach

4.84 out of 5 average rating, 128 reviews

*WATERFRONT BEACH HOUSE PARADISE*

Come enjoy a true piece of paradise at Colonial Beach! With 3 bedrooms and 2 bathrooms, there's plenty of room for you to enjoy a long weekend away. Wake up to the rising sun and enjoy a cup of coffee on the deck before taking a stroll down to the beach. Watch the ducks and occasional swan swim by as the sun sets over the water. You'll never want to leave!

Sep 9 – 16

G$36,021 GYD per night

Guest favorite

Home in Colonial Beach

4.99 out of 5 average rating, 198 reviews

Beach Blonde Cottage

Coastal farmhouse style cottage recently renovated and on "The Point" in Colonial Beach. Located 3 blocks from the water on a quiet street. Downtown attractions are close enough to walk, bike or access by golf cart. Dahlgren per diem welcome.

Jan 28 – Feb 4

G$33,010 GYD per night

Guest favorite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 261 reviews

Bayview Bungalow

Escape the pace of city life to relaxed and charming Colonial Beach! Come down with your boat and tie up at the dock or get some remote work done with super fast wifi. This space is newly remodeled and ready to be experienced now!

Nov 18 – 25

G$26,329 GYD per night