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

9.6 out of 10, Exceptional, (20)
"Completely enjoyed my stay at Olu’s property. The townhouse is cozy, clean and comfortable. Really appreciate the variety of drinks, coffee and snacks. Olu also left a Christmas basket with goodies. So thoughtful ! I always cook when I rent and there was a full complement of dishes, utensils and pots and pans. Everything you need to make meals.Although there were no football games during my stay, the parking pass would have definitely been utilized. So thoughtful to include the pass.I will...
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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. "
Rooftop Deck Escape! Free Parking!

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

10.0 out of 10, Exceptional, (206)
"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!

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

9.8 out of 10, Exceptional, (181)
"2nd time here and love it! "
The price is AU$334
includes taxes & fees
14 Jan - 15 Jan
'At Fells Point' CitySide - 'Tons better than a hotel!'

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (28)
"What a fantastic location, central to everything in the city. Parked the car and walked everywhere. The house is perfect!!"
The price is AU$1,049
includes taxes & fees
14 Jan - 15 Jan
Freshly renovated 3-story home 1 block from USNA!

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

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

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (57)
"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"
Recently Renovated Annapolis Home - Conveniently Located

Tranquility Awaits

10.0 out of 10, Exceptional, (14)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

9.4 out of 10, Exceptional, (29)
"10/10 would recommend. "
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Quirky Baltimore Townhome ~ 2 Mi to Inner Harbor

9.2 out of 10, Wonderful, (9)
"Great location within walking distance to Camden Yards!!"
Quirky Baltimore Townhome ~ 2 Mi to Inner Harbor

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (20)
"We had the best time at this rental — it was accessible, cozy, stocked with things like good toilet paper (silly, but we noticed and appreciated!), and in an amazing location! Absolutely recommend! "
Charming Historic Townhouse Steps From USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (48)
"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

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$1,046
includes taxes & fees
14 Jan - 15 Jan
Luxe Houseboat: Breathtaking Skyline 360 Views

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

10.0 out of 10, Exceptional, (12)
"It was an amazing stay and the owner is very responsive and kind. I would recommend this property 10/10 for anyone who is looking for a clean and spacious home! "
The price is AU$591
includes taxes & fees
14 Jan - 15 Jan
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

Cozy Modern Micro Apt in the Heart of Fells Point!

9.4 out of 10, Exceptional, (18)
"At first site I was Leary but a neighborhood garage owner befriended us and made sure we were safe by even setting up cones in the street to secure a parking space. The host Mr. Smith was very kind and patient and provided all the info we needed. The apartment was clean and had all the amenities we required. It was a challenge with the winding staircase for 3 senior ladies but we got along fine climbing them several times a day. I loved the historical feel of the brick and staircase.. Mr. Smith...
The price is AU$429
includes taxes & fees
21 Jan - 22 Jan
Cozy Modern Micro Apt in the Heart of Fells Point!

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
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, (2154)
"Great spot"
The price is AU$226
includes taxes & fees
20 Jan - 21 Jan
Renaissance Baltimore Harborplace Hotel

Hyatt Place Baltimore Inner Harbor

3.5 star property
8.2 out of 10, Very good, (1830)
"Staff was awesome. Great job. "
The price is AU$177
includes taxes & fees
2 Feb - 3 Feb
Hyatt Place Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4.0 star property
8.2 out of 10, Very good, (1636)
"Very good location for the game "
The price is AU$222
includes taxes & fees
20 Jan - 21 Jan
Hyatt Regency Baltimore Inner 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.