Cobb Island vacation rentals

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Top-rated vacation rentals in Cobb Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Colonial Beach

4.97 out of 5 average rating, 116 reviews

Sunnyside Up - Dog Friendly Waterfront Cottage

Our classic cottage has beautiful expansive views of the Potomac River. Wake up to stunning sunrises & enjoy coffee in our screened front porch, or sit & relax on our own private pier. Our home is equipped with comfortable linens, a fully stocked kitchen, Smart TV, Wi-Fi, & a secluded outdoor dining area with a gas grill, fire pit & fenced yard. We are just blocks away from the public beach, downtown shops, boardwalk, and restaurants. Golf cart rentals can be reserved thru local companies

Guest favorite

Home in Leonardtown

5 out of 5 average rating, 107 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Guest favorite

Cabin in Colonial Beach

4.95 out of 5 average rating, 133 reviews

Summer 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.

Guest favorite

Guesthouse in Bushwood

4.93 out of 5 average rating, 150 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.

Guest favorite

Rental unit in Lexington Park

5 out of 5 average rating, 352 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!

Guest favorite

Guesthouse in Colonial Beach

4.94 out of 5 average rating, 108 reviews

Delaney’s Compound- Great deals on longterm stays!

Delaney’s Compound includes a Guest House accommodating 2 - 3 people. Your pet is welcome with pre-approval & $75 fee. Great deals on long-term stays! The Guest House was built using lumber and other charming elements reclaimed from the original farmhouse outbuilding (circa 1889). There’s a cozy fireplace for snuggling and a second floor balcony for coffee or cocktails. Sparkling clean, fully furnished and ready to welcome you!

Guest favorite

Cottage in California

4.97 out of 5 average rating, 219 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that 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 featuring live concerts by top name bands.

Guest favorite

Home in Colonial Beach

4.97 out of 5 average rating, 144 reviews

Potomac View - riverfront, wraparound porch

Relax and unwind in this historic Victorian home with a wonderful wraparound porch and views of the river right across the street. This home is perfectly situated right off the Potomac River, peaceful and secluded from the main downtown area, yet close enough to walk to the public beaches and restaurants. Feel right at home in this 145 year old home, complete with its share of historic charm and modern updates.

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 601 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. 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.

Guest favorite

Cottage in Montross

4.98 out of 5 average rating, 133 reviews

Newly Renovated 2BR Waterfront Cottage with Dock

Escape to Mallard Cottage, our newly renovated home nestled along the picturesque Nomini Creek. Step onto the private dock for direct water access, where you can launch one of our paddleboards or kayaks for a day of exploration. Highlights include: ✔ 4 Outdoor Decks ✔ High-Speed Wi-Fi ✔ Central Heating & Air Conditioning ✔ Game Room ✔ Free Parking ✔ No Cleaning Fee

Guest favorite

Guest suite in Colonial Beach

4.88 out of 5 average rating, 108 reviews

Private entrance 2 bedroom suite in new home

Walk to a secluded beach or enjoy a fire in the fire pit on the grass outside your suite. Private unit with outside entrance in new home. Two queen bedded rooms plus a sofa that converts to a queen bed in the living room. Quiet area close to all the fun Colonial Beach has to offer.

Guest favorite

Guest suite in Montross

4.98 out of 5 average rating, 149 reviews

Loft in Montross

Furnished studio apartment above Montross Brewery and Beer Garden. ***note: the brewery itself is closed for the season—this doesn’t affect the loft*** Private, modern, clean, and secluded. We are Roxanne & Ben and although we live in Utah we are happy to host your stay!