Search Cottages in Southern Maryland

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Compare 76 Cottages in Southern Maryland with updated reviews, rates, and availability.

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is AED 551
AED 1,141 total
includes taxes & fees
1 Dec - 2 Dec
Soul Oasis - home on the Chesapeake Bay

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (11)
"Adorable cottage with updated amenities. A great retreat for friends or a family!! "
Updated North Beach Cottage: Pet Friendly!

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (10)
"This was the perfect cottage for our family's fall getaway to St. Mary's! The host was wonderfully communicative and the cottage was perfectly appointed for our little get away. We will definitely be back!"
2 Bedroom Cozy Beach Cottage with Beach Access

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Sunrise Waterfront Cottage with Dock & Kayaks!

9.6 out of 10, Exceptional, (20)
"We had a great time here. The property was exactly what we were looking for. It was remote and quite. We loved the dock and water access. We fished off the dock two days. Pulled in a couple of medium sized Red fish and a few other smaller varieties. This would be a great fishing spot with small kids. Beds were super comfortable. "
Sunrise Waterfront Cottage with Dock & Kayaks!

Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H

9.6 out of 10, Exceptional, (90)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H

Enchanting West River Retreat

10.0 out of 10, Exceptional, (7)
"Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again. "
Enchanting West River Retreat

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is AED 514
AED 1,071 total
includes taxes & fees
1 Dec - 2 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach

Waterfront Cottage in Piney Point w/ Kayaks!

7.6 out of 10, Good, (4)
"First, this was a last minute booking, due to our inability to stay at our original rental. Becky was responsive to our needs so we could vacate our previous rental without delay. Next, what I loved about this property, and something you do not get very often is the amount of living, relaxing space there is in this rental. Several areas for groups of people to spread out, watch TV, look at the water, play games, often times while there are several bedrooms, there are precious few places for...
Waterfront Cottage in Piney Point w/ Kayaks!

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more. "
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (86)
"This house is beautiful and has everything anyone could ask for. The scenery is spectacular too. We enjoyed sitting outside watching the sun set, just listening to the water and enjoying a fire on the beach. The kitchen is any cook's dream! The owners are wonderful and communicated with us wonderfully. We would give it a 10 rating if possible and will certainly be back. One of our best vacations!"
Piney Point, private , Beach Front Cottage

Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

10.0 out of 10, Exceptional, (4)
"What a wonderful quick getaway weekend from DC! The quiet neighborhood, front row river views, and wonderful hospitality was unmatched! What a great way to get to know St Mary’s County!"
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

10.0 out of 10, Exceptional, (14)
"My husband and I and our grown kids and dog stayed for 3 weeks at Rodo Beach House. The weather was mostly beautiful. The house is lovely and had everything we needed, including comfy beds! The owner is friendly and easy to contact. We had great fires in the firepit. Comfortable outside chairs around the fire pit as well as on the beach. The bay is incredibly clean, and the small private beach is perfect for people and dogs. The neighborhood, beach and surroundings are private, quiet and...
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (27)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay

WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

10.0 out of 10, Exceptional, (62)
"We had a great time, cottage adorable and updated."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is AED 1,194
AED 1,441 total
includes taxes & fees
27 Nov - 28 Nov
Cottage Located on the Patuxent River!
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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Other property types in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is AED 551
AED 1,141 total
includes taxes & fees
1 Dec - 2 Dec
Soul Oasis - home on the Chesapeake Bay
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.

Frequently asked questions

How much do cottages in Southern Maryland cost?
Expect to pay between AED 514 and AED 1,194 per night for cottages in Southern Maryland. No matter your budget, a fantastic stay is only a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southern Maryland?
Explore our 76 cottages in Southern Maryland and reserve your favorite. Whether you’re thinking about a family vacay or a break with friends, your perfect stay is just clicks away with Expedia.
Why book your cottage in Southern Maryland with Expedia?
Reserving a cottage in Southern Maryland is as easy as clicking on your travel dates and picking your ideal place for a getaway in nature. From luxurious retreats to low-cost stays and cottages that include perks like free WiFi, Expedia has something for all styles. As for terrific deals? We’ve got your back!
How can I find cheap cottages in Southern Maryland?
An excellent way to uncover cheap cottages in Southern Maryland is with Expedia’s useful filter tool. Tailor your search results by budget, amenities and star rating to land awesome bargains in just a few keystrokes.