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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Southern Maryland and around

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, (139)
"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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, (71)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Cozy Cottage with access to and partially obstructed views of the bay.
Beach nearby

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

9.0 out of 10, Wonderful, (26)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Terrace/patio

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

10.0 out of 10, Exceptional, (1)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!
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, (152)
"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
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (49)
"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
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Soul Oasis - home on the Chesapeake Bay
Sun-loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"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 €276
includes taxes & fees
18 Aug - 19 Aug
Soul Oasis - home on the Chesapeake Bay
2 Bedroom Cozy Beach Cottage with Water Access
Fridge, microwave, oven, stovetop

2 Bedroom Cozy Beach Cottage with Water Access

9.6 out of 10, Exceptional, (17)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Water Access
Walk to Beach: Pet-Friendly Gem in Scotland!
Beach nearby

Walk to Beach: Pet-Friendly Gem in Scotland!

10.0 out of 10, Exceptional, (3)
"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!
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Property grounds

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.
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Chesapeake Bay Vacation Rental w/ Boat Dock!
Interior

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!
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

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
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, (16)
"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
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Smart TV, books

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

9.6 out of 10, Exceptional, (4)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is €311
includes taxes & fees
2 Sept - 3 Sept
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Property grounds

WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

10.0 out of 10, Exceptional, (67)
"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
Property grounds

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
Cottage Located on the Patuxent River!
Sun-loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"The accommodations were superb and being on the water was amazing!"
The price is €317
includes taxes & fees
9 Aug - 10 Aug
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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Top Southern Maryland Hotel Reviews

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Holiday Inn Express Washington DC East - Andrews AFB by IHG

10/10 Excellent
"Great service "
Paul 2-night trip
Posted 2 days ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG

Frequently asked questions

How much do cottages in Southern Maryland cost?
Cottages in Southern Maryland range between €276 and €317 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.
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.