Search Vacation Homes in Western Shore of Maryland

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 941 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!
Miscellaneous

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

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place 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
Property grounds

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

9.6 out of 10, Exceptional, (75)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
House on the Gwynns Falls
Outdoor dining

House on the Gwynns Falls

8.8 out of 10, Excellent, (12)
"Mary was great to deal with, very accommodating, and happily welcomed our dog. It was super convenient when visiting dear friends nearby."
The price is AEDĀ 621
AEDĀ 942 total
includes taxes & fees
12 May - 13 May
House on the Gwynns Falls
Affordable Luxury Town Home in Federal Hill Baltimore.
Fridge, microwave, oven, stovetop

Affordable Luxury Town Home in Federal Hill Baltimore.

9.6 out of 10, Exceptional, (41)
"Our 4th time at this property. Manager is responsive and accommodating. The home is comfortable, clean and well appointed. Excellent location in safe, walkable neighborhood. Free street parking. Highly recommend. "
Affordable Luxury Town Home in Federal Hill Baltimore.
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"Clean and nice location. Worked perfectly for our visit to the area to spend time with our daughter, son-in-law, and two perfect grandsons. Thank you for sharing your beautiful home and location. "
Waterfront Wildlife Retreat on the Patuxent River
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

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.
Interior

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"This house was in a fantastic location! It is within walking distance to downtown Annapolis and anything you might need or want. It is a cute little home with all of your needed comforts. "
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (74)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage
Cozy 2BR Retreat with Free Parking & Prime Location
Aerial view

Cozy 2BR Retreat with Free Parking & Prime Location

9.6 out of 10, Exceptional, (29)
"Awesome Host and Beautiful home. I will stay again"
Cozy 2BR Retreat with Free Parking & Prime Location
Stylish 3BD 2BA Rancher Near BWI, FT Meade, Live Casino, Baltimore!
Fridge, microwave, oven, stovetop

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
Terrace/patio

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 Iā€™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
View from property

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio

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

9.8 out of 10, Exceptional, (60)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Entire House by the Fells Point, JHU.
Fridge, microwave, oven, stovetop

Entire House by the Fells Point, JHU.

9.8 out of 10, Exceptional, (21)
"Home was clean and location was convenient. Had a great stay."
Entire House by the Fells Point, JHU.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

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

10.0 out of 10, Exceptional, (114)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Charming Home: Parking, Sleeps 10, WFH Space
Fridge, microwave, oven, stovetop

Charming Home: Parking, Sleeps 10, WFH Space

2.0 star property
10.0 out of 10, Exceptional, (6)
"A great place to stay with homie accommodations.Would definitely use again if traveling through Baltimore."
Charming Home: Parking, Sleeps 10, WFH Space
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"The home is absolutely beautiful and Dina is a great host. My family and I have full intentions of coming back!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

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

2.0 star property
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Cozy home away from home
Fridge, microwave, oven, stovetop

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
Lobby

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
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (22)
"Perfect family get away with a great view!"
The price is AEDĀ 511
AEDĀ 1,094 total
includes taxes & fees
11 May - 12 May
Soul Oasis - home on the Chesapeake Bay
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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.