Vacation rentals in Cobb Island

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Top-rated vacation rentals in Cobb Island

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Guest favourite

Tiny homes in Saint Inigoes

4.98 out of 5 average rating, 294 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Sep. 15 – 22

$127 CAD per night

Guest favourite

Guest suite in Warsaw

4.98 out of 5 average rating, 107 reviews

The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private suite at the river's edge, features panoramic views of the Rappahannock River and farmland. Enjoy fiery sunsets and sunrises, starry night skies, eagles, ospreys and more. You can swim, fish, explore waterways by kayak, or bike in tranquil, rural surroundings. Savor your morning coffee on the balcony with sounds of songbirds, or relax by the river with a book and local wine. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

Jul. 23 – 30

$189 CAD per night

Guest favourite

Cottage in Leonardtown

4.97 out of 5 average rating, 126 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.

Apr. 9 – 16

$300 CAD per night

Guest favourite

Cottage in California

4.97 out of 5 average rating, 195 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.

Mar. 1 – 8

$155 CAD per night

Guest favourite

Loft in Lusby

5.0 out of 5 average rating, 315 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Mar. 14 – 21

$206 CAD per night

Guest favourite

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.

Oct. 3 – 10

$218 CAD per night

Guest favourite

Cabin in Colonial Beach

4.97 out of 5 average rating, 103 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.

Dec. 14 – 21

$227 CAD per night

Guest favourite

Guesthouse in Bushwood

4.92 out of 5 average rating, 144 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.

Mar. 19 – 26

$143 CAD per night

Guest favourite

Apartment in Lexington Park

5.0 out of 5 average rating, 316 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!

Dec. 26 – Jan. 2

$138 CAD per night

Guest favourite

Tiny homes in Solomons

4.95 out of 5 average rating, 541 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.

Dec. 25 – Jan. 1

$221 CAD per night

Guest favourite

Home in Colonial Beach

5.0 out of 5 average rating, 200 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.

Sep. 13 – 20

$257 CAD per night

Guest favourite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 263 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!

Oct. 24 – 31

$206 CAD per night