Book a Southern Maryland Cottage

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Relax on the lakeside deck with two comfortable lounge chairs and a shaded area.

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

9.8 out of 10, Exceptional, (137)
"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
Cottage Located on the Patuxent River!
Walk along the beach to the wooden pier, where the calm waters await.

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"A gorgeous property perfect for a quiet getaway from the city noise. The cottage is very charming, and perfect for two people. Very clean, accommodating, private and peaceful. The private beach is beyond charming and the local spots are amazing. We recommend the frying pan and highly HIGHLY recommend the spider hall farm stand (get the apple cobbler). Nonetheless the cottage is truly amazing and a perfect get away. "
The price is NZ$611
includes taxes & fees
22 July - 23 July
Cottage Located on the Patuxent River!
1 min Walk to Beach July 20-29 Available: Hideaway in Hays Beach Chesapeake Bay
Enjoy cooking in this well-equipped kitchen with a double oven, large refrigerator, and shelf.

1 min Walk to Beach July 20-29 Available: Hideaway in Hays Beach Chesapeake Bay

10.0 out of 10, Exceptional, (116)
"It was a great stay!"
1 min Walk to Beach July 20-29 Available: Hideaway in Hays Beach Chesapeake Bay
Private Beach Front Getaway at The Sunshine Beach Cottage.
Enjoy the serene ocean view from the comfort of your indoor space.

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (70)
"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 Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Relax in this inviting space with a sofa, coffee table, and potted plant, offering views of the outdoors through large windows.

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 NZ$628
includes taxes & fees
23 July - 24 July
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Relax in a serene outdoor setting with a tranquil body of water and lush green surroundings.

WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

10.0 out of 10, Exceptional, (66)
"We had a great time, cottage adorable and updated."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Hays Beach House - Hot Tub - Private Beach
Enjoy the ocean view from the deck, featuring a comfortable seating area with a table and chairs.

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
Updated North Beach Cottage: Pet Friendly!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large island, and a sink.

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (16)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Cozy Cottage with access to and partially obstructed views of the bay.
Guests can enjoy a serene beach scene with a clear view of the ocean.

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

9.2 out of 10, Wonderful, (25)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Enjoy a serene lakeside escape with a picnic table and access to a pebbly beach.

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

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is NZ$502
includes taxes & fees
22 July - 23 July
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Relax in a serene outdoor space surrounded by lush greenery and trees, featuring a fire pit and comfortable seating.

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!
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, oven, and microwave, along with a large sink and gold faucet.

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

10.0 out of 10, Exceptional, (48)
"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
Soul Oasis - home on the Chesapeake Bay
Escape to a serene beach paradise surrounded by lush greenery and the soothing sound of gentle waves.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (30)
"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 NZ$526
includes taxes & fees
27 July - 28 July
Soul Oasis - home on the Chesapeake Bay
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Escape to a serene retreat surrounded by lush greenery and mature trees, where a peaceful porch beckons.

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

10.0 out of 10, Exceptional, (11)
"Everything we needed, relaxing visit"
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Relax by the pool surrounded by lounge chairs and outdoor seating.

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
2 Bedroom Cozy Beach Cottage with Beach Access
Enjoy cooking in this well-equipped kitchen with a water dispenser and nearby seafood restaurant.

2 Bedroom Cozy Beach Cottage with Beach Access

9.8 out of 10, Exceptional, (16)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Beach Access
North Beach Cottage - Walk to Chesapeake Bay
Enjoy a game of pool in this room with a pool table and expansive views of the backyard through large windows.

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
Chesapeake Bay Vacation Rental w/ Boat Dock!
Enjoy ocean views from the deck, featuring a bench and flat-screen TV.

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!
Waterfront Island Cottage with Loft and Private Pier
Relax by the serene lake with a peaceful grassy area, dock, and scenic views.

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
Dock Access: Waterfront Cottage in Avenue!
Fridge, microwave, stovetop, coffee/tea maker

Dock Access: Waterfront Cottage in Avenue!

Dock Access: Waterfront Cottage in Avenue!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 "
Joe 2-night trip
Posted 1 day 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 NZ$502 and NZ$628 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 98 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.