Search Western Shore of Maryland Cottage Rentals from CA $207

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Aug 15 - Aug 17
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Browse Select Western Shore of Maryland Cottages

The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
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)
"The accommodations were superb and being on the water was amazing!"
The price is CA $416
CA $498 total
includes taxes & fees
Aug 5 - Aug 6
Cottage Located on the Patuxent River!
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!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
House w/Water Views of Rock Creek 2BA 2BA Cottage
Relax in this serene outdoor space with a wicker sofa, glass table, and wooden bench.

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (29)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Perfect location for USNA Commissioning Week
Relax in this open-plan living area featuring a central island, dining space, and comfortable seating.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
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, (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
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Situated by a serene body of water, this bench offers a tranquil view of the surrounding shoreline.

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (29)
"Peaceful, quiet venue with hiking trails and a beautiful location! My family and I enjoyed the lovely home and downtown Annapolis where we savored delicious seafood and quality family-time. The hosts were responsive and the home was charming! Thank you for the terrific experience!"
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Situated in a serene, environment, this charming house offers a welcoming entrance and a tranquil atmosphere.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (213)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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, (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
The Yellow Cottage on Harness Creek
Traditional house with a front porch surrounded by lush gardens and flowering plants.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (161)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
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
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Enjoy serene sunsets over a peaceful lake or sea from a tranquil beach with a tree and rocks.

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and stainless steel appliances.

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
House (3 Bedrooms) | Interior

Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!

3.0 star property
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is CA $620
CA $1,023 total
includes taxes & fees
Aug 5 - Aug 6
Secluded Cozy Cottage in Historic Downtown
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Relax on the dock with Adirondack chairs and enjoy the serene view.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is CA $496
CA $910 total
includes taxes & fees
Aug 5 - Aug 6
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Relax under a thatched umbrella in a serene outdoor setting surrounded by lush greenery.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
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 Western Shore of Maryland Hotel Reviews

The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

10/10 Excellent
"Convenient location. Very nice how it seems secluded to being in your vehicle for valet which is convenient. Quiet atmosphere. Bed is comfortable but could give better or more pillows as they were very flat. "
Lauren 1-night trip
Posted 12 hours ago
The Royal Sonesta Harbor Court Baltimore