Western Shore of Maryland Holiday Rentals

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Holiday Rentals 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)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
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

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (10)
"We only stayed one night but the house was perfect for our needs. The main family room/kitchen area was perfect for all of us to comfortably sit together, and the bedroom layout was great for two families (two “wings”). The hosts were super responsive and accommodating. Would just suggest two hairdryers (one in each bathroom - if there was a second, we did not see it) and shower soap. The bed in the primary bedroom was very comfortable and everything went smoothly. "
The price is AU$849
includes taxes & fees
1 Dec - 2 Dec
Edgewater/Mayo Getaway!

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$607
includes taxes & fees
8 Dec - 9 Dec
Luxury 4 bed King Suite! Mins to Towson!

2BR Luxury Apartment Rooftop Pool & Gym

9.4 out of 10, Exceptional, (20)
"Overall it was pleasant. There as one little glitch, but it was out of your control. An evaluation due to a kitchen fire on the sixteenth floor. 27 flights of floors was very overwhelming. My 85 year old husband required assistance from the last 5 flights."
2BR Luxury Apartment Rooftop Pool & Gym

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (175)
"Super cute department. Has everything that you need and is very comfortable. Lots of super cute touches. In an awesome neighborhood, super walkable and close to all of the fun things and Fells Point."
The price is AU$319
includes taxes & fees
23 Dec - 24 Dec
'At Fells Point' CitySide - 'Tons better than a hotel!'

Distinguished Apartment Rooftop Deck

3.0 star property
8.8 out of 10, Excellent, (6)
"I would def come back again for the views this place has to offer. Great stay with all the amenities I needed. Thank you! "
Distinguished Apartment Rooftop Deck

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$1,402
includes taxes & fees
4 Dec - 5 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!

Rooftop Deck Escape! Free Parking!

9.0 out of 10, Wonderful, (23)
"Good location, close to Light Street. House was nice, enjoyed the rooftop deck with fire table. "
The price is AU$434
includes taxes & fees
26 Nov - 27 Nov
Rooftop Deck Escape! Free Parking!

2-story, riverfront home with private dock, inviting deck & dog-friendly yard

9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard

Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown

10.0 out of 10, Exceptional, (24)
"It was an amazing time and everything was lovely in the house!"
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown

'At Fells Point' Courtyard - Your historically restored apartment

9.6 out of 10, Exceptional, (79)
"The place was just as expected, the neighborhood is cute and quiet, the pub next door is great, and the water is a short walk away. Will likely stay here again. "
The price is AU$371
includes taxes & fees
23 Dec - 24 Dec
'At Fells Point' Courtyard - Your historically restored apartment

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$626
includes taxes & fees
25 Nov - 26 Nov
Downtown Home - Close to Topgolf, Ravens Stadium, Orioles Park, UM Baltimore

Luxe Houseboat: Breathtaking Skyline 360 Views

10.0 out of 10, Exceptional, (12)
"Gorgeous floating home - wonderful windows to appreciate the fabulous water views Excellent rooftop space - comfy bed and sleep sofa - beautifully appointed kitchen and bathroom "
The price is AU$1,179
includes taxes & fees
23 Dec - 24 Dec
Luxe Houseboat: Breathtaking Skyline 360 Views

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

10.0 out of 10, Exceptional, (10)
"Beautiful home"
The price is AU$558
includes taxes & fees
19 Dec - 20 Dec
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
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 types of properties in Western Shore of Maryland you may be interested in

Renaissance Baltimore Harborplace Hotel

4.0 star property
8.6 out of 10, Excellent, (2180)
"Clean and close to the Harbor"
The price is AU$183
includes taxes & fees
23 Dec - 24 Dec
Renaissance Baltimore Harborplace Hotel

Hyatt Place Baltimore Inner Harbor

3.5 star property
8.2 out of 10, Very good, (1754)
"Restaurant on the bottom of the hotel was amazing"
The price is AU$174
includes taxes & fees
23 Dec - 24 Dec
Hyatt Place Baltimore Inner Harbor

Holiday Inn Baltimore BWI Airport, an IHG Hotel

3.0 star property
9.2 out of 10, Wonderful, (1009)
"always a pleasure staying here. everyone is very pleasant and tends to your needs. bed is most comfirtable too!! I would reccommend this hotel to all !!"
The price is AU$180
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Baltimore BWI Airport, an IHG Hotel
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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