Cottage vacation rentals in Southern Maryland

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Top-rated cottage rentals in Southern Maryland

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Guest favorite

A serene outdoor seating area features four Adirondack chairs arranged around a wooden platform, facing a calm, reflective body of water. The scene is framed by trees and showcases a vibrant sunset with hues of orange and pink over the horizon.

Cottage in Cambridge

4.97 out of 5 average rating, 141 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Great for winter remote work! Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Guest favorite

The kitchen area features a dark countertop and white cabinetry, complemented by three high-backed stools at the island. Modern light fixtures hang above, creating a well-lit space. Black appliances and open shelving add functionality, while a dining area with a wooden table is visible in the background.

Cottage in Warsaw

4.94 out of 5 average rating, 113 reviews

Modern 2 Bdrm Cottage in Historic River Community

Remodeled river cottage available in historic, quaint Sharps. Explore this old fishing village by land or water, and enjoy perusing local artwork and farm stands. Framed by a marsh/old marina, open fields, and the Rappahanock River across the street, this unique property is just the getaway you’ve been looking for! Bicycles and paddle boards on site. Escape to a slower pace, picturesque views, and birder’s paradise, watch the osprey and eagles sail past!

Top guest favorite

Two Adirondack chairs are positioned beside a wooden dock, shaded by a large umbrella. The view overlooks calm water surrounded by greenery, creating a serene environment. A small table is present between the chairs, enhancing the inviting outdoor seating area.

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

An outdoor grilling area is featured with a stainless steel grill positioned beside a wooden staircase. Colorful flowerpots hang nearby, adding a touch of greenery. A hose is coiled beside the grill, with nearby picnic tables visible in the background.

Cottage in Colonial Beach

4.93 out of 5 average rating, 168 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Top guest favorite

A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.

Cottage in California

4.97 out of 5 average rating, 232 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

Cottage in Deale

4.82 out of 5 average rating, 178 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

Top guest favorite

A cottage entrance is framed by trees, leading to a spacious outdoor area that opens up to a view of the water. Sunlight filters through the trees, highlighting the inviting natural surroundings.

Cottage in Hague

4.99 out of 5 average rating, 147 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Guest favorite

A sandy beach stretches along the Chesapeake Bay, where two colorful lounge chairs are positioned near the water's edge. Lush greenery and a manicured lawn are visible in the background, complemented by nearby cottages that offer a serene atmosphere.

Cottage in Deale

4.96 out of 5 average rating, 158 reviews

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

Top guest favorite

An outdoor deck features comfortable seating with two rocking chairs and an outdoor sofa, arranged around a propane fire pit. A vibrant orange umbrella provides shade, overlooking the tranquil water of Nomini Creek, with lush greenery and a private dock in the background.

Cottage in Montross

4.98 out of 5 average rating, 152 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

Guest favorite

The exterior of the cottage features a welcoming entrance with a white door and a porch supported by white columns. Symmetrical windows on either side enhance the facade. The garden includes low shrubs, and a gravel pathway leads to the entrance, framed by well-maintained grass.

Cottage in Leesburg

4.93 out of 5 average rating, 229 reviews

The Cottage at Stone Tower Winery

The Cottage at Stone Tower Winery is a fully renovated, one-bedroom house located only an hour from DC, 30 minutes from Dulles Airport, and 15 minutes from Leesburg. The home is perfectly situated to enjoy a peaceful stay in the country and serves as an ideal location to explore the Northern Virginia wine region and historic Loudoun County.

Guest favorite

Cottage in Colonial Beach

4.96 out of 5 average rating, 101 reviews

Hawthorn Cottage Great In-town Location!

Just steps away from the beach and within walking distance to shops, restaurants and all the towns amenities, Hawthorn Cottage has everything to make our guests feel right at home. This beautifully decorated cottage in the waterfront town of Colonial Beach, Virginia is the perfect destination for those in search of a peaceful retreat.

Guest favorite

The cottage exterior showcases charming blue shingles and a welcoming front porch, furnished with a bench and four chairs. A spacious deck offers outdoor seating and is surrounded by lush greenery and flower beds, enhancing the warm ambiance of the property.

Cottage in Tracys Landing

4.89 out of 5 average rating, 364 reviews

Charming Waterfront on Chesapeake Bay

Perched on a bank overlooking expansive views of the Chesapeake Bay, our shingled cottage is a comfortable country retreat with exposed beams and cathedral ceilings. It is less than an hour to Annapolis and Washington DC. Save on your first Airbnb stay (some restrictions apply): https://abnb.me/e/i9PHYamHUN

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What guests are saying

Waterfront Cottage with Beautiful Sunset Views

4.94 out of 5 average rating, 31 reviews6 months ago

We absolutely loved Phillip’s incredibly charming and cozy cottage! The interior is gorgeous and the exterior waterfront view will take your breath away! We spent a lot of time fishing on the dock and loved eating our bountiful catch! Lots to explore nearby in the quaint small towns of the Northern Neck! Phillip was very quick to respond to my many questions and always offered local recommendations which we really appreciated! We did a quick run to Walmart to get firewood for the outdoor pit, bait and $9 camping chairs. The chairs made our dock fishing more comfortable than the built-in dock bench. My advice is run, don’t walk, to secure a reservation at this stunning waterfront oasis! We can’t wait to return! K Helms, Clifton, VA

Cottage in Lancaster

What guests are saying

The Garden Cottage of Colonial Beach

4.9 out of 5 average rating, 39 reviews9 months ago

This is our yearly spot to visit for our family beach trip, and it again did not disappoint. IMO this home provides one of the best values you will find, with a full kitchen, multiple bedrooms, and plenty of room to spread out. It is also walkable to the beach and restaurants, and the hosts treat us (and everyone) like family. Just book it and you won’t regret it!

Cottage in Colonial Beach

What guests are saying

Weems Creek Cottage, Annapolis Waterfront

4.98 out of 5 average rating, 112 reviews2 weeks ago

What a beautiful off the beaten path place to stay. You are within walking distance of restaurants, coffee, and grocery. But feel like you’re miles away. That’s the effect the cabin has on you. There is a beautiful waterfront that you can enjoy from just about every area of the home. Jim was more than helpful. He really went above and beyond over most host. We would definitely Stay again. It’s the perfect spot if you need to relax.

Cottage in Annapolis

What guests are saying

Cottage on Cabin Creek

4.95 out of 5 average rating, 61 reviews2 months ago

My husband and I traveled here for a night away from our children and work responsibilities. We were looking for some place that was private and on the water. This place was both and it did not disappoint! The loft was cozy and spacious and we loved looking out the windows at the water and rain. It was very clean and there were plenty of towels and blankets and other special touches. Janelle communicated with us ahead of time to make sure she was ready for our arrival and she was kind and responsive throughout the process. We also found it easy to get into Easton for dinner at The Stewart, which was a treat, and then return back to the cabin. I would stay here again in a heartbeat -- but hopefully for longer next time.

Cottage in East New Market

What guests are saying

Quiet Coastal Cottage Escape with Water Views

4.9 out of 5 average rating, 101 reviews4 months ago

We used Lindsey's location as a home away from home while our employee was stationed on a long-term project. It was very nice to have a spot that was flexible and cozy for him to stay in lieu of a hotel. Lindsey was flexible with us and very communicative and open to our questions and requests. Thank you so much, Lindsey!

Cottage in North Beach

What guests are saying

Harbor Cottage

4.97 out of 5 average rating, 37 reviews1 month ago

The home and property were peaceful and quiet. We especially loved the spacious, (all weather) sunny enclosed porch. The kitchen and family room were comfy and had everything we needed. We walked the neighborhood with our dogs and the beach was beautiful as well as relaxing. Such a wonderful weekend get away.

Cottage in Montross

What guests are saying

Waterfront Chesapeake Bay Sunrises w/Private PIER!

4.99 out of 5 average rating, 153 reviews3 weeks ago

Heather’s place is a little paradise on the water. Peaceful, quiet, and perfect for some real rest and relaxation. The house was exactly as described—spotless, all new, and super comfortable inside, with beautiful outdoor spaces to enjoy. Annapolis is just a short 25-minute drive away if you’re looking for great food and things to do. Communication with Heather was easy and fast. I’d come back anytime I’m in the area again!

Cottage in Edgewater

What guests are saying

River + Beach Front Cottage 4 BR ADA Northern Neck

5 out of 5 average rating, 31 reviews6 months ago

We had a wonderful long weekend here! The house is well-equipped and David was even able to secure fishing and crabbing gear so our two kids could try to catch dinner. It is a quiet street of cottages with friendly neighbors in a gorgeous location - the view is so calming. We enjoyed exploring the local area (love the coffee shop and brewery in Montross), kayaking, swimming, and relaxing on the big screened porch. A feature here that you don’t always have at the shore is a great sandy beach! Can’t wait to come back for another getaway.

Cottage in Kinsale

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