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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, (209)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
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

9.8 out of 10, Exceptional, (71)
"Great location in quiet neighborhood."
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, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes

House on the Gwynns Falls

8.6 out of 10, Excellent, (10)
"Mary was a very gracious host and very accommodating when we added a 6th person at the last minute. She was always very responsive when I messaged her and greeted us with a warm welcome when we arrived. The house is a beautiful historic home tucked away in quiet neighborhood "
The price is AED 621
AED 806 total
includes taxes & fees
4 Apr - 5 Apr
House on the Gwynns Falls

Affordable Luxury Town Home in Federal Hill Baltimore.

9.6 out of 10, Exceptional, (39)
"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

10.0 out of 10, Exceptional, (159)
"The house was awesome, the view couldn’t have been better. Loved everything about it, quiet and peaceful and it is on a dead end short road with wildlife in the yard in the morning, deer, fox, blue heron, bald eagle, geese and ducks, just fabulous. Will definitely be going back soon I hope."
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

9.8 out of 10, Exceptional, (70)
"This property is lovely. So close to my daughter it’s a perfect weekend getaway. "
Sweet Bamboo Beach Cottage

Cozy 2BR Retreat with Free Parking & Prime Location

9.6 out of 10, Exceptional, (24)
"Great trip- thank you! "
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

19 Mi to Baltimore: Townhome in Maryland City

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
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, (59)
"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.

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."
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

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (138)
"We enjoyed our stay as much as the 1st time. Great spot for an Annapolis getaway! House is comfortable and location is ideal. Gracious and responsive host."
Your Annapolis Adventure Starts Here!!

Charming Home: Parking, Sleeps 10, WFH Space

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was great. Fit the 8 of us perfectly. Parking is on the street and first come first served so you may not be right in front of the rental. Arming and disarming the alarm was easy. We had one issue and the agent was easy to reach and help troubleshoot the issue. "
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
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

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

10.0 out of 10, Exceptional, (209)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Cozy and blocks from M&T Stadium/Camden Yards

9.6 out of 10, Exceptional, (31)
"We needed a place to stay for a conference that was cheaper than the expensive hotel the conference was in. This place was perfect. Close location, clean, easy to book and access. Parking is expensive so be ready for that. Cheapest is 22/day. Still cheaper than the hotel by far. "
The price is AED 349
AED 921 total
includes taxes & fees
6 Apr - 7 Apr
Cozy and blocks from M&T Stadium/Camden Yards

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
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.