Photo by Ann Sair

Search Southern Maryland Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Southern Maryland cottages

Exterior
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (39)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$254 nightly
The price is $269
Jan 4 - Jan 5, 2026
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Property grounds
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$268 nightly
The price is $284
Dec 26 - Dec 27
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Interior
Commute to Alexandria & DC: Home w/ Shared Yard

Commute to Alexandria & DC: Home w/ Shared Yard

Commute to Alexandria & DC: Home w/ Shared Yard
3.0 star property
Waldorf
$474 nightly
The price is $524
Dec 25 - Dec 26
Total with taxes and fees
Commute to Alexandria & DC: Home w/ Shared Yard
Exterior
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (8)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
$287 nightly
The price is $317
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$260 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Property grounds
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.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
$271 nightly
The price is $299
Dec 25 - Dec 26
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior
Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
$300 nightly
The price is $317
Dec 25 - Dec 26
Total with taxes and fees
Cottage Located on the Patuxent River!
House (3 Bedrooms) | Interior
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
$815 nightly
The price is $905
Dec 30 - Dec 31
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Exterior
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

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Aurora Highlands
10.0 out of 10, Exceptional, (28)
"Very nice accommodations; very attractive. Parking spot is a huge plus. Thanks for great stay!"
United States
Anonymous traveler
$286 nightly
The price is $327
Jan 6 - Jan 7, 2026
Total with taxes and fees
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Exterior
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
Colonial Beach
9.8 out of 10, Exceptional, (15)
"We love going to Colonial Beach. This house offered everything we were looking for in a mini vacation."
United States
Anonymous traveler
$406 nightly
The price is $452
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Dec 25 - Dec 26
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 26 - Dec 27
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Marina
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
$506 nightly
The price is $577
Jan 5 - Jan 6, 2026
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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.
View all properties
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

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

10/10 Excellent
"We went for the ice show and it didn’t disappoint. We usually go to Gaylord National in the summer but this year wanted to experience ICE Polar Express. The front desk staff was very accommodating as we initially had a room on the back end of the hotel because Atrium rooms weren’t available at the time of booking. We were able to transfer to an Atrium room on the morning of our second day. The view didn’t disappoint as usual. Next time my husband said we will see if we can book the Presidential Suite. Pricey yes, but well worth it! "
Lionel 3-night trip
Posted 2 days ago
Gaylord National Resort & Convention Center

Find out more about Southern Maryland

Southern Maryland Cottages information

Number of reviews
205
Accommodation
95 Cottages
Lowest Price
$269
Highest Price
$905

Frequently asked questions

How much do cottages in Southern Maryland cost?
Cottages in Southern Maryland range between $269 and $905 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 95 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