Search Cottages in Western Shore of Maryland

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Western Shore of Maryland and around

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!
The Heron's Nest at Atlantic Marina
Enjoy the ocean view from this outdoor space with a deck and columned roof.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
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, (162)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Relax on the spacious outdoor deck with a comfortable sofa and bench, surrounded by lush greenery and a wooden railing.

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
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Enjoy al fresco dining and social gatherings on this shaded deck with a grill and comfortable seating.

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
Cozy cabin nestled in a forest setting, featuring a front entrance with a door and stairs.

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 €277
includes taxes & fees
18 Aug - 19 Aug
Soul Oasis - home on the Chesapeake Bay
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 €704
includes taxes & fees
7 Sept - 8 Sept
Secluded Cozy Cottage in Historic Downtown
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Situated in a wooded area, this house features a front porch and a well-maintained lawn.

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!
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Stunning two-story house with a gabled roof and inviting front porch, set amidst a beautifully maintained garden.

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
North Beach Cottage - Walk to Chesapeake Bay
Stunning two-story house with a central entrance, flanked by windows, and a charming dormer window above.

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
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (6)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Stroll up to this charming two-story home with a welcoming front porch and garage, set amidst a beautifully manicured lawn.

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!
Cottage Located on the Patuxent River!
Set amidst lush greenery, this charming single-story building offers a serene retreat.

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 €318
includes taxes & fees
11 Aug - 12 Aug
Cottage Located on the Patuxent River!
Updated North Beach Cottage: Pet Friendly!
Cozy home with a gabled roof and a welcoming front porch.

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!
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Relax on the deck surrounded by a lush lawn and a majestic tree, with a table and chairs perfect for outdoor dining.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is €585
includes taxes & fees
11 Aug - 12 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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!
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Situated in a serene garden, this charming shed offers a simple, functional space.

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

8.8 out of 10, Excellent, (5)
"My wife and I stayed at this property for a few days and loved it! The owner was very responsive and was very accommodating. I could really feel the pride in ownership of this cottage that the owner has. There was a very informative welcome booklet with easy to follow instructions for the home and with information about the area. The cottage is centrally located between North Beach and Chesapeake Beach, so it was the best of both words. We can't wait to go back!"
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Ruscincy’s Rest "minutes drive to Orioles stadium"
Exterior

Ruscincy’s Rest "minutes drive to Orioles stadium"

Ruscincy’s Rest "minutes drive to Orioles stadium"
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

Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

10/10 Excellent
"Close johns Hopkins "
Jacqueline 2-night trip
Posted 8 hours ago
Hyatt Place Baltimore Inner Harbor

Frequently asked questions

How much do cottages in Western Shore of Maryland cost?
Prepare to pay between €277 and €704 per night for cottages in Western Shore of Maryland. No matter your budget, a wonderful stay is just clicks away on Expedia. 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 Western Shore of Maryland?
Western Shore of Maryland has 74 cottages to choose from. Click on your travel dates, enter your destination and plan your perfect trip today.
Why book your cottage in Western Shore of Maryland with Expedia?
Booking a cottage in Western Shore of Maryland is as easy as working out your travel dates and picking your ideal place for outdoor recreation and relaxation. From upmarket retreats to low-cost stays and cottages that come with amenities like a kitchenette, Expedia has something for all tastes and styles. As for irresistible deals? We've got them too!