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Browse Select Southern Maryland Cottages

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Terrace/patio

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
Cottage Located on the Patuxent River!
Exterior

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 CA $416
CA $498 total
includes taxes & fees
Aug 4 - Aug 5
Cottage Located on the Patuxent River!
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Exterior

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
Hays Beach House - Hot Tub - Private Beach
Terrace/patio

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
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior

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

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 CA $225
CA $483 total
includes taxes & fees
Sep 2 - Sep 3
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
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Terrace/patio

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 CA $248
CA $413 total
includes taxes & fees
Aug 4 - Aug 5
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Updated North Beach Cottage: Pet Friendly!
Exterior

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"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.
Beach nearby

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

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
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
Soul Oasis - home on the Chesapeake Bay
Exterior

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 CA $207
CA $433 total
includes taxes & fees
Aug 5 - Aug 6
Soul Oasis - home on the Chesapeake Bay
2 Bedroom Cozy Beach Cottage with Beach Access
Exterior

2 Bedroom Cozy Beach Cottage with Beach Access

9.6 out of 10, Exceptional, (17)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Beach Access
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.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Exterior

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
Chesapeake Bay Vacation Rental w/ Boat Dock!
Outdoor dining

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!
North Beach Cottage - Walk to Chesapeake Bay
Exterior

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
Waterfront Island Cottage with Loft and Private Pier
Exterior

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!
Terrace/patio

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.
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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
"Customer Service is exceptional"
Srikant 1-night trip
Posted 2 days ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG