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Featured Cottages in Southern Maryland

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

10.0 out of 10, Exceptional, (122)
"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

Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies

10.0 out of 10, Exceptional, (155)
"As always, loved our stay here! One of our favorite places for fishing! "
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.

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

9.8 out of 10, Exceptional, (147)
"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

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

10.0 out of 10, Exceptional, (51)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

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

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (91)
"Wonderful hosts, beautiful property! Already planning next years visit! "
Piney Point, private , Beach Front Cottage

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

10.0 out of 10, Exceptional, (18)
"The house was very nice and had great amenities supplied by the owners. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

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 NZ$506
includes taxes & fees
9 Oct - 10 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2 Bedroom Cozy Beach Cottage with Water Access

9.6 out of 10, Exceptional, (19)
"Cottage was neat and tidy, close to decent eats, close to the beach, and was a lovely getaway."
2 Bedroom Cozy Beach Cottage with Water Access

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (33)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
The price is NZ$525
includes taxes & fees
6 Oct - 7 Oct
Soul Oasis - home on the Chesapeake Bay

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

10.0 out of 10, Exceptional, (124)
"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

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

10.0 out of 10, Exceptional, (14)
"Everything we needed, relaxing visit"
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Cottage on the Bay

8.0 out of 10, Very good, (2)
"We had a wonderful visit! The cottage was exceptionally equipped with towels, kitchen, beach chairs, wood for the fire pit, ect. "
Cottage on the Bay

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!

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

9.8 out of 10, Exceptional, (40)
"The house was very clean with all needed amentities plus. Mary was very responsive to any questions, including suggestions of local beaches. The view is incredible, especially late evening. Location wise, you are within 1-2 hours of several major cities. Will definitely plan to stay here for any future trips!"
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!
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
912
Accommodation
99 Cottages
Lowest Price
NZ$506
Highest Price
NZ$525

Frequently asked questions

How much do cottages in Southern Maryland cost?
Cottages in Southern Maryland range between NZ$506 and NZ$525 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 99 cottages to choose from. Enter your destination and travel dates and lock in your next escape today.
What is there to do in Southern Maryland near my cottage?
There are many attractions to explore when holidaying in Southern Maryland. If you're thinking about a day or two in Upper Marlboro, Lake Presidential Golf Club shouldn't be missed.

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