Photo by Meg Faller

Search Southern Maryland Cottage Rentals from CA $206

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Check prices for these dates

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Nov 20 - Nov 22
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Nov 27 - Nov 29
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Dec 11 - Dec 13
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Jan 8 - Jan 10

Our top choices for Southern Maryland cottages

A covered porch with a table and chairs, overlooking a grassy area and a body of water.

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

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $230
CA $380 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

2. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $207
CA $399 total
includes taxes & fees
Dec 1 - Dec 2
Soul Oasis - home on the Chesapeake Bay
A porch with a door, a window, and a grill table with chairs.

3. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $488
CA $770 total
includes taxes & fees
Nov 22 - Nov 23
Plum Point Cottage #14
Fire pit (2)

4. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $486
CA $811 total
includes taxes & fees
Nov 22 - Nov 23
Plum Point Cottage #15
A single-story house with a front porch, a small deck, and a wooden walkway leading to the door.

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (22 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is CA $317
CA $595 total
includes taxes & fees
Nov 22 - Nov 23
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A red house with a porch decorated with pumpkins and flowers.

6. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $729
CA $1,632 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront Cabin Near Solomons Island w/ Hot Tub
A covered patio with a table and chairs, large windows, and an American flag.

7. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
Plum Point Cottage #17
A house with a red door, a small porch, and a view of a river with a bridge in the background.

8. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $369
CA $510 total
includes taxes & fees
Nov 22 - Nov 23
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A single-story house with a porch, a wooden fence with a neon sign, and a welcome flag.

9. The Sugar Shack - charming, fully renovated 1930s cottage with AC

The Sugar Shack - charming, fully renovated 1930s cottage with AC
Colonial Beach
The price is CA $250
CA $461 total
includes taxes & fees
Dec 7 - Dec 8
The Sugar Shack - charming, fully renovated 1930s cottage with AC
A house with a gravel driveway leading to a dock by the water.

10. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (57 reviews)
"My family and I had a great time at this property fishing and crabbing. We also did a day trip to Westmoreland State Park, where we got to hike to Fossils Beach."
United States
Carmelita A.
The price is CA $250
CA $464 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Virginia Potomac Riverfront Cottage
A wooden deck with wicker furniture, a round table, and a fire pit.

11. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is CA $514
CA $901 total
includes taxes & fees
Nov 16 - Nov 17
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A single-story house with a front porch, a small deck, and a number '4' on the side.

12. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $492
CA $582 total
includes taxes & fees
Nov 16 - Nov 17
2 Bedroom Cottage at Coles Point Marina
A building with a black metal gate, a brick pathway, and greenery.

13. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is CA $642
CA $1,015 total
includes taxes & fees
Nov 15 - Nov 16
Secluded Cozy Cottage in Historic Downtown
A two-story house with a steep gable roof, large windows, and a front porch.

14. Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Aurora Highlands
10.0 out of 10, Exceptional, (44 reviews)
"Owner was very attentive and responsive to our needs. Home was cozy, close to the metro and restaurants. We enjoyed our stay and highly recommended!"
United States
Rick H.
The price is CA $271
CA $514 total
includes taxes & fees
Dec 7 - Dec 8
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
A wooden deck with a chair and a table, overlooking a lake with a grassy area and a fence.

15. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is CA $388
CA $462 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront Home Firepit BWI Marleycreek River
A two-story house with a garage, a front porch, and a well-maintained lawn.

16. Downtown DC Home w/ Furnished Patio!

Downtown DC Home w/ Furnished Patio!
3.0 star property
Southeast
The price is CA $806
CA $1,742 total
includes taxes & fees
Dec 3 - Dec 4
Downtown DC Home w/ Furnished Patio!
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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Learn more about Southern Maryland

Experience the family-friendly area of Southern Maryland—a scenic waterfront, sports teams, and sights from Running Hare Vineyard to Budds Creek Motocross Park.

See all hotels in Southern Maryland
A white house with a red roof and a white lighthouse.
Photo by Meg Faller
Open Photo by Meg Faller

Top reviews in Southern Maryland

An aerial view of a modern urban area with a large green space, a red double-decker bus, and contemporary buildings with glass facades.
The Watermark Hotel

The Watermark Hotel

The Watermark Hotel
Tysons

10/10 Excellent

Whenever I travel to DC I always stay at The Watermark. Tysons corner is perfectly situated and an easy drive to Dulles not to mention the convenient train ride to see the monuments and Smithsonian. Thank you,
Canada
Peter
Reviewed June 21, 2026
The Watermark Hotel

Frequently Asked Questions

How much do cottages in Southern Maryland cost?

Cottages in Southern Maryland range between CA $206 and CA $805 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 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.

How can I find cheap cottages in Southern Maryland?

An excellent way to locate cheap cottages in Southern Maryland is with Expedia's convenient filter tool. Refine your search results by budget, amenities and star rating to take advantage of awesome prices in just a few keystrokes.

What is there to do in Southern Maryland near my cottage?

There are many attractions to explore when vacationing in Southern Maryland. If you're thinking about a day or two in Upper Marlboro, Lake Presidential Golf Club shouldn't be missed.

Explore a world of travel with Expedia