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Featured Cottages in Southern Maryland

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (73)
"Everything was as advertised. Clean and tidy. Easy to find. Had everything we needed while visiting some state parks. Kids loved the beach and already asked to go back"
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

9.8 out of 10, Exceptional, (145)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (5)
"The owner was very nice "
The price is AU$462
includes taxes & fees
3 Sept - 4 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies

10.0 out of 10, Exceptional, (155)
"We enjoyed fishing on the dock and the house was clean/comfortable. Would stay here again."
Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies

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

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (3)
"The house was in a perfect location. Close to the beach and restaurants. The home was very comfortable, cozy and thoughtfully decorated. We will definitely be back!"
Quick walk to the beach! Fire pit, Corn hole, Games & More!

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (32)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is AU$487
includes taxes & fees
2 Sept - 3 Sept
Soul Oasis - home on the Chesapeake Bay

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

10.0 out of 10, Exceptional, (12)
"Everything we needed, relaxing visit"
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"
Hays Beach House - Hot Tub - Private Beach

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (39)
"Beautiful, charming house! The owner was wonderful! She had a lovely card waiting for us with a handwritten note. Really warm welcome! Also great location!"
North Beach Cottage - Walk to Chesapeake Bay

WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

10.0 out of 10, Exceptional, (68)
"We had a great time, cottage adorable and updated."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

Waterfront Island Cottage with Loft and Private Pier

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was everything we hoped for and more. Impeccably clean, beautifully maintained, and the view was just breathtaking — even better than the photos. The host was incredibly responsive and helpful, which made our stay even more seamless and enjoyable. Every detail was perfect, and we loved every minute. We’ll definitely be back and highly recommend this gem!! Thanks, Allen. "
Waterfront Island Cottage with Loft and Private Pier

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

9.6 out of 10, Exceptional, (91)
"We had a great time at this place. Close enough to walk to town if necessary would definitely book again for a weekend getaway."
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (41)
"The accommodations were superb and being on the water was amazing!"
The price is AU$547
includes taxes & fees
2 Sept - 3 Sept
Cottage Located on the Patuxent River!

Dock Access: Waterfront Cottage in Avenue!

Dock Access: Waterfront Cottage in Avenue!

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (118)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10.0 out of 10, Exceptional, (122)
"Host is awesome, available to answer questions and just excited for her guests to enjoy their stay! "
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Chesapeake Bay Vacation Rental w/ Boat Dock!

7.8 out of 10, Good, (14)
"Had a lovely relaxing stay with swimming, kayaking, and quality time with family. Looking forward to another stay in the future."
Chesapeake Bay Vacation Rental w/ Boat Dock!
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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Top Southern Maryland Hotel Reviews

Find out more about Southern Maryland

Find out more about Southern Maryland

Southern Maryland Cottages information

Number of reviews
Accommodation
99 Cottages
Lowest Price
AU$462
Highest Price
AU$547

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Southern Maryland cost?
Rates for cottages in Southern Maryland range between AU$462 and AU$547 per night. No matter your budget, you're sure to find a perfect place to get in tune with nature. This price was 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?
Choose from 99 cottages in Southern Maryland. Whether you're travelling with the family, as a couple or with a group of best friends, Expedia is here to help you find an ideal place.
What is there to do in Southern Maryland near my cottage?
The most important travel accessory for your Southern Maryland trip is an epic itinerary! Prince Georges Stadium, Belair Mansion and Allen Pond Park are among the top sights if you're off to Bowie. La Plata also has lots of fantastic attractions, such as Port Tobacco Players. Need more ideas for your to-do list? Drop by Hawthorne Country Club and College of Southern Maryland too.