Southern Maryland Cottages
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Cottages in Southern Maryland
![Cozy Cottage with access to and partially obstructed views of the bay.](https://images.trvl-media.com/lodging/75000000/74290000/74287500/74287426/18d4cc1d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy Cottage with access to and partially obstructed views of the bay.
![Soul Oasis - home on the Chesapeake Bay](https://images.trvl-media.com/lodging/94000000/93250000/93249900/93249890/w1015h683x5y0-2a4f1433_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Soul Oasis - home on the Chesapeake Bay
![Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing](https://images.trvl-media.com/lodging/31000000/30050000/30044100/30044084/b2852d76_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
![Private Beach Front Getaway at The Sunshine Beach Cottage.](https://images.trvl-media.com/lodging/69000000/68440000/68437600/68437545/8fb34648_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Private Beach Front Getaway at The Sunshine Beach Cottage.
![Hays Beach House - Hot Tub - Private Beach](https://images.trvl-media.com/lodging/94000000/93830000/93825000/93824932/4689d7bc_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hays Beach House - Hot Tub - Private Beach
![Enchanting West River Retreat](https://images.trvl-media.com/lodging/106000000/105710000/105701500/105701490/ab8fa8b9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Enchanting West River Retreat
![Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb](https://images.trvl-media.com/lodging/35000000/34010000/34006900/34006852/822a8c51_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
![Waterfront Cottage in Piney Point w/ Kayaks!](https://images.trvl-media.com/lodging/95000000/94680000/94674100/94674043/93ca6396_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Waterfront Cottage in Piney Point w/ Kayaks!
![2 Bedroom Cozy Beach Cottage with Beach Access](https://images.trvl-media.com/lodging/99000000/98530000/98524500/98524460/311ee870_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
2 Bedroom Cozy Beach Cottage with Beach Access
![Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/825de017_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
![Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
![Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/36d81978_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Southern Maryland Cottage Accommodation
You’re on the go every day, working hard and making that cash. But if you haven’t taken a holiday in months, it’s time to rethink your life choices. It’s time for you to look into Southern Maryland holiday cottages and take a day off—or ten days. Because once you’re all settled in, you won’t want to leave.
Words like charming, adorable, and delightful probably come to mind when you think of country cottages, set in lovely little towns the world over. The same applies to beach cottages—just replace the rolling hills with lapping waves. And while Southern Maryland cottages can’t be in every setting at once, you’ll find that the stunning scenery here is better than all the others combined. Cottages are the perfect retreat from everyday life, with serene surroundings both inside and out and that relaxed vibe that can come only from knowing everything is taken care of. Southern Maryland has an equally charming vibe, and that’s why so many travellers love it.
“Don’t worry, be happy” should be your motto on your next holiday. Well, friend, in Southern Maryland, that’s not just the motto of visitors; the locals are living that theme every day. So take a break from that presentation you’re working on and make a different graph instead—of Wotif’s low prices on over Southern Maryland cottage accommodation options. It’s about time you got to kick back, and we don’t mean putting your feet up at your desk.
Southern Maryland Cottages essential information
Accommodation | 76 Cottages |
---|---|
Lowest Price | NZ$126 |
Highest Price | NZ$563 |
Popular accommodation | Cozy Cottage with access to and partially obstructed views of the bay., Soul Oasis - home on the Chesapeake Bay, Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing, Private Beach Front Getaway at The Sunshine Beach Cottage., Hays Beach House - Hot Tub - Private Beach, Enchanting West River Retreat, Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb, Waterfront Cottage in Piney Point w/ Kayaks!, 2 Bedroom Cozy Beach Cottage with Beach Access, Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK, Relaxing, peaceful house in Calvert County, Md close to beach towns and DC., Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch. |
More Cottages
More accommodations in Southern Maryland
Top trending hotels in Southern Maryland
![Gaylord National Resort & Convention Center](https://images.trvl-media.com/lodging/2000000/1780000/1777200/1777196/65072f6b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
Gaylord National Resort & Convention Center
More destinations for you
^Eligibility requirements and conditions apply