Search Vacation Homes in Western Shore of Maryland

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Compare 947 Vacation Homes in Western Shore of Maryland with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"We stayed at the host property for a long weekend in town for a family baby shower nearby. We were totally impressed with the cleanliness of the location, spacious accommodations and responsiveness of the host. There is a weekend farmers market and we wound up getting fresh produce to cook and some great food and desserts to eat. Parking was a breeze and the nearby park was wonderful for our daily walks. Highly recommended! 10 out of 10!!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes

House on the Gwynns Falls

8.6 out of 10, Excellent, (11)
"The house is a gem. Very unique older home. Very comfortable and welcoming. Renovations are almost complete. The house is pet friendly. The location is perfect if you enjoy hiking trails, friendly neighbors and a view of the falls. "
The price is SAR 634
SAR 819 total
includes taxes & fees
27 Apr - 28 Apr
House on the Gwynns Falls

Affordable Luxury Town Home in Federal Hill Baltimore.

9.6 out of 10, Exceptional, (40)
"Great house super clean, comfortable beds! The backyard was super cute and comfy if you like outside. only downsides are there’s not parking in the front of the house, had to park BLOCKS away. the front door also got stuck a few times making me think the door was locked but other then that great location and everything! "
Affordable Luxury Town Home in Federal Hill Baltimore.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"We came out from Hawaii to see my Daughter and Grand Daughters.The over all experience from start to finish at the property was easy and flawless. Some days it was just my wife and I and other days it was with my grand daughters spending the night, they also enjoyed the stay. There is plenty of room. The property has an excellent view and we saw some wild life. We would stay at this property again and would highly recommend it to others.A hui hou,"until we meet again," Mark and Tamara"
Waterfront Wildlife Retreat on the Patuxent River

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "
Historic Annapolis Home 1.5 blocks from center of town.

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"Needed a little quiet time, and the fresh air. Had a nice time. The house is clean,stocked with basic essentials. The beds are comfortable, that is super important to me, I also enjoyed the color choices and decorations. Tracy was prompt and thorough. I’d stay again . "
Sweet Bamboo Beach Cottage

Cozy 2BR Retreat with Free Parking & Prime Location

9.6 out of 10, Exceptional, (28)
"We were in Baltimore for a short get away and to see a baseball game at Camden and this was a perfect spot! Sky was very accommodating and the property was well set up for our stay. We were able to park right by the house and walk to Camden yards and the inner harbor. It has pretty much all the kitchen tools you might need and even has a lovely outdoor space too. Definitely recommend! Thanks!"
Cozy 2BR Retreat with Free Parking & Prime Location

Stylish 3BD 2BA Rancher Near BWI, FT Meade, Live Casino, Baltimore!

Stylish 3BD 2BA Rancher Near BWI, FT Meade, Live Casino, Baltimore!

19 Mi to Baltimore: Townhome in Maryland City

6.0 out of 10, (1)
"Enjoyed the location. Property is nice, but with a few issues. I wouldn't stay here again.The guest contact responded quickly to our early check in request. She told me to contact her with any concerns. After checking in, we could not get ceiling fans to work - so I sent her a text. She never responded. I contacted her after we left because I’d forgotten some clothing. Again - she never responded. My son lives nearby and could have picked up my clothes for me - but now I guess I get to buy...
19 Mi to Baltimore: Townhome in Maryland City

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (60)
"My husband and I took our boys ten and twelve over easter break. The property was very private. The expansive views of the yard looking out to the bay we're beautiful. The house was really clean and nicely decorated . The master bedroom had great views and the bed was amazing. It might be to buy the mattress! We were unable to put our boat in. Due to the water levels and the sludge. But we found a boat launch only ten minutes away. All in all, if you want a very relaxing vacation, this is it....
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Entire House by the Fells Point, JHU.

9.8 out of 10, Exceptional, (21)
"Typical row house with lots of stairs but very clean & comfortable. Loved having a pack & play for our 2 year old granddaughter. Host was very nice. Would stay again."
The price is SAR 465
SAR 884 total
includes taxes & fees
27 Apr - 28 Apr
Entire House by the Fells Point, JHU.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Charming Home: Parking, Sleeps 10, WFH Space

2.0 star property
10.0 out of 10, Exceptional, (6)
"We were there for a conference and use the house for saving cost and team building. "
Charming Home: Parking, Sleeps 10, WFH Space

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"This house was just like the listing: clean, bright, and beautiful. The beds were comfortable and the kitchen was well-appointed. Even though it rained and we couldn't use the fire pit, the bird-watching was excellent! "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Cozy home away from home

7.8 out of 10, Good, (6)
"Property was as listed and was cleanl"
Cozy home away from home
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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Other property types in Western Shore of Maryland

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (23)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

One bedroom at Baltimore Covention Ctr

4.0 star property
One bedroom at Baltimore Covention Ctr
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.