Holiday Homes in Western Shore of Maryland

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Featured Holiday Homes in Western Shore of Maryland

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (10)
"TVs don’t work. Tile by fridge broken. Dangerous. House is awesome. Hot tub works great. If fixed we will be back for Skibs games. Cheers. Ty !! "
The price is AU$836
includes taxes & fees
1 Dec - 2 Dec
Edgewater/Mayo Getaway!

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

House on the Gwynns Falls

10.0 out of 10, Exceptional, (4)
"Mary's home is lovely! She is welcoming and kind and the check-in process is simple. I would stay at the home in the future."
The price is AU$342
includes taxes & fees
30 Nov - 1 Dec
House on the Gwynns Falls

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

10.0 out of 10, Exceptional, (16)
"Perfect place for Ravens Game. Walking distance to stadium. Super clean. Nice neighbors. Responsive host. "
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

The GRACE Villa - a homey affair!

9.2 out of 10, Wonderful, (7)
"The house a was clean and beautiful, very cozy with plenty of room. The pool was a little cloudy and the the bottom of the pool was coming up and it wasn't filtering the water Right. Over all I would love to stay at this home again wasn't filtering right.beautiful and warm but wasa"
The GRACE Villa - a homey affair!

Private Waterfront Woods | Dock, Kayaks, Views

10.0 out of 10, Exceptional, (14)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views

Luxury 4 bed King Suite! Mins to Towson!

8.4 out of 10, Very good, (9)
"We had a wonderful time with friends and family. The location was great and the home was really nice. Thank you."
The price is AU$603
includes taxes & fees
8 Dec - 9 Dec
Luxury 4 bed King Suite! Mins to Towson!

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

9.8 out of 10, Exceptional, (59)
"This condo was absolutely perfect. It is super cute and clean. Three bedrooms as advertised. Very quiet area. We love the fact that it has a piano. We would definitely love to stay here again. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA

Stylish 4-bedroom whole house with plenty of parking

9.2 out of 10, Wonderful, (15)
" It was great "
Stylish 4-bedroom whole house with plenty of parking

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (12)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house for a fun weekend. Super clean and comfortable. Withing walking distance of good restaurants and stadiums. Will definately look to book this location again when we are back in Baltimore."
Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,357
includes taxes & fees
9 Dec - 10 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (11)
"The Bennett House not only lived up to its pictures online, the cleanliness, abundance of extra special touches, communication with the host, and more surpassed our expectations. The beds were extra comfy, the kitchen, fully stocked, the bathrooms, adorned with the fluffiest white towels and extra toiletries . . . and I can't say enough about the front porch. Even though clouds cloaked the sky when we arrived and when we left, sunshine streamed through our Annapolis trip because of the Bennett...
Bennett House (entire):Haven in Historic Annapolis

Downtown Home - Close to Topgolf, Ravens Stadium, Orioles Park, UM Baltimore

7.8 out of 10, Good, (8)
"The property had many rooms, and the back yard was nice. Other than that it had a musty smell/ smelled like cats when we first entered. The ceiling in the basement was maybe 6/7 ft high where we had to duck while walking around. The air conditioning was set on 70 with a lock, which was fine, BUT it didn’t work in the top two rooms where the temp was well over 90 during the day. It’s a good place to stay for one or two nights but if you plan on doing longer I wouldn’t recommended it. I will say...
The price is AU$635
includes taxes & fees
8 Dec - 9 Dec
Downtown Home - Close to Topgolf, Ravens Stadium, Orioles Park, UM Baltimore
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

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

10.0 out of 10, Exceptional, (16)
"Perfect place for Ravens Game. Walking distance to stadium. Super clean. Nice neighbors. Responsive host. "
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.
Beautiful view of the beach with palm trees

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