Holiday Homes in Western Shore of Maryland

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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Holiday Homes in Western Shore of Maryland

Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

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

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Timekeeping and dining in a serene, stylish space with a dining area for two and a touch of greenery.

Canton’s Finest Luxury Stay: Walk to Park, Bars!

9.8 out of 10, Exceptional, (16)
"The host was great, the place was adorable and perfect for our stay. Very clean, had everything we needed and was close to everything. I highly recommend!"
The price is NZ$520
includes taxes & fees
28 July - 29 July
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Affordable Luxury Town Home in Federal Hill Baltimore.
Enjoy cooking in this well-equipped kitchen with a granite countertop, wooden cabinets, and modern appliances.

Affordable Luxury Town Home in Federal Hill Baltimore.

9.4 out of 10, Exceptional, (51)
"Our third stay at this property. Very clean and comfortable. Everything that you need is walking distance. House is well appointed and as pictured. "
Affordable Luxury Town Home in Federal Hill Baltimore.
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (112)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Entire House by the Fells Point, JHU.
Kitchen features a stainless steel stove, oven, and digital control panel, along with a coffee station and utensil holder.

Entire House by the Fells Point, JHU.

9.4 out of 10, Exceptional, (24)
"Home was clean and location was convenient. Had a great stay."
The price is NZ$577
includes taxes & fees
5 Aug - 6 Aug
Entire House by the Fells Point, JHU.
Cozy Annapolis Cottage
Relax on the outdoor deck surrounded by lush greenery and trees, featuring a sofa set, wicker chair, and small table.

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (12)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Enjoy cooking in this well-equipped kitchen with a dishwasher, sink, and range hood.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (14)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

Rising Sun Bay View Cottage
Charming Historic Annapolis Home With Two Off-street Parking Places!
Staircase leads to a warm and inviting interior with a fireplace and wooden door.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (189)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Stroll up to the charming entrance, where a brick pathway leads to a cozy home with a red door and inviting porch.

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

9.8 out of 10, Exceptional, (45)
"This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again. "
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is NZ$909
includes taxes & fees
25 Aug - 26 Aug
Edgewater/Mayo Gateaway w/ Hot Tub
Waterfront Wildlife Retreat on the Patuxent River
Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (166)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (65)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Charming single-story house with a front porch and well-manicured lawn.

Bayfront Maryland Retreat w/ Deck, Near Beaches!

9.8 out of 10, Exceptional, (9)
"Lovely, serene, comfortable, waterfront home. Conveniently close to the essentials, restaurants, pier, beach, markets, and more. "
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Pet-Friendly Annapolis Home: Walk to Beach!
Enjoy a peaceful seaside escape with a gentle sea and a rocky breakwater.

Pet-Friendly Annapolis Home: Walk to Beach!

9.2 out of 10, Wonderful, (13)
"Great neighborhood, relaxing proorrty with alot of outdoor seating"
Pet-Friendly Annapolis Home: Walk to Beach!
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Enjoy meals in the spacious dining area with a glass-top table and comfortable seating.

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

9.6 out of 10, Exceptional, (4)
"Nice house in a quiet, safe, residential neighborhood. Clean and comfortable. Easy access to all the attractions in Baltimore. "
The price is NZ$827
includes taxes & fees
28 July - 29 July
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
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

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

10/10 Excellent
"I liked staying in the Inner Harbor because it was so convenient to restaurants and shops."
Corless 2-night trip
Posted 8 hours ago
Renaissance Baltimore Harborplace Hotel