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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 93 Cottages in Southern Maryland with updated reviews, rates, and availability.

Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (25)
"Teresa was awesome. "
The price is AED 551
AED 1,145 total
includes taxes & fees
5 Jun - 6 Jun
Soul Oasis - home on the Chesapeake Bay
Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

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

9.2 out of 10, Wonderful, (20)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (34)
"The place was wonderful, clean and well stocked. It was a great place to stay - kudos to the hosts for an inviting atmosphere."
North Beach Cottage - Walk to Chesapeake Bay
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (134)
"Lovely, quiet, clean and comfy "
The price is AED 558
AED 899 total
includes taxes & fees
9 Jun - 10 Jun
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Piney Point, private , Beach Front Cottage
Property grounds

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (86)
"Wonderful hosts, beautiful property! Already planning next years visit! "
Piney Point, private , Beach Front Cottage
Discounted Summer & Fall Dates: The Hideaway in Hays Beach - Chesapeake Bay
Beach nearby, sun loungers, beach towels

Discounted Summer & Fall Dates: The Hideaway in Hays Beach - Chesapeake Bay

10.0 out of 10, Exceptional, (114)
"A wonderful place to just relax. We loved being able to walk on the beach as well as just sit in the backyard relaxing and chatting! House is clean and well-stocked and had different areas for gathering! "
Discounted Summer & Fall Dates: The Hideaway in Hays Beach - Chesapeake Bay
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

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

10.0 out of 10, Exceptional, (44)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (66)
"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.
2 Bedroom Cozy Beach Cottage with Beach Access
Fridge, microwave, oven, stovetop

2 Bedroom Cozy Beach Cottage with Beach Access

9.8 out of 10, Exceptional, (15)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Beach Access
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Marina

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

9.8 out of 10, Exceptional, (36)
"We had a great stay in this quiet beautiful house. Annapolis was close by and a fun time."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies
Aerial view

Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies

10.0 out of 10, Exceptional, (149)
"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
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beach nearby

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (14)
"We had a very nice time at this house. The neighborhood was very nice to walk in and we enjoyed watching the Bay."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Hays Beach House - Hot Tub - Private Beach
Smart TV, fireplace, books

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
Walk to Beach: Pet-Friendly Gem in Scotland!
Beach nearby

Walk to Beach: Pet-Friendly Gem in Scotland!

10.0 out of 10, Exceptional, (2)
"This cute and comfortable cottage had everything I could need. The community beach was lovely and spotted deer on my walks. It was just a quick drive to Point Lookout. I thoroughly enjoyed my stay!"
Walk to Beach: Pet-Friendly Gem in Scotland!
Cottage on the Potomac in Newburg: Shared Pier!
Miscellaneous

Cottage on the Potomac in Newburg: Shared Pier!

10.0 out of 10, Exceptional, (2)
"Our 5-night stay at this coastal getaway was nothing short of amazing! This charming VRBO property exceeded our expectations. The house was spotless, beautifully decorated, and equipped with everything we needed for a relaxing vacation. The open living space and modern kitchen made it easy to feel at home, and the cozy bedrooms ensured restful nights. The location was perfect for morning strolls and sunset views. The host was incredibly responsive and provided great local tips. This was the...
Cottage on the Potomac in Newburg: Shared Pier!
Waterfront Island Cottage with Loft and Private Pier
Miscellaneous

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
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (91)
"Great property right outside of north beach"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Property grounds

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

10.0 out of 10, Exceptional, (112)
"Perfect little getaway! Missy is wonderful to work with and the property was perfect for making memories over a holiday weekend with my family! Thanksgiving dinner, movies, games and cold plunges will be something we will always remember. Missy we would love to return!!!!"
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Miscellaneous

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

9.0 out of 10, Wonderful, (2)
"The owner was very nice "
The price is AED 735
AED 1,189 total
includes taxes & fees
9 Jun - 10 Jun
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Chesapeake Bay Vacation Rental w/ Boat Dock!
Interior

Chesapeake Bay Vacation Rental w/ Boat Dock!

8.0 out of 10, Very Good, (12)
"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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Frequently asked questions

How much do cottages in Southern Maryland cost?
Cottages in Southern Maryland range between AED 551 and AED 735 per night. These stays offer a chance to get in touch with nature — at a price you can afford. 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?
Southern Maryland has 93 cottages to choose from. Enter your destination and travel dates and lock in your next escape today.
Why book your cottage in Southern Maryland with Expedia?
Expedia has some excellent cottages in Southern Maryland, so get ready for a memorable stay close to nature. If you need to stick to a budget, choose how much you’d like to spend and the star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We’ll help you find the right digs whatever your bank balance or plans.