Search Vacation Homes in Western Shore of Maryland

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Compare 783 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, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.8 out of 10, Exceptional, (57)
"Enjoyed these accomodations! Spacious and comfortable. Accessible parking and lovely neighborhood!."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Bay views with kayaks, bikes, fire pit, crabbing and more
9.4 out of 10, Exceptional, (16)
"We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon."
Bay views with kayaks, bikes, fire pit, crabbing and more
Canton’s Finest Luxury Stay: Walk to Park, Bars!
9.6 out of 10, Exceptional, (8)
"Darling place located close to everything you need -- restaurants, coffee shops, drug stores, and Safeway. Quiet neighborhood to boot. The manager was very responsive to any questions. This place is a definite "yes"."
The price is AED 400
AED 1,032 total
includes taxes & fees
11 Nov - 12 Nov
Canton’s Finest Luxury Stay: Walk to Park, Bars!
USNA family Waterfront Paradise just minutes from Annapolis and Baltimore, MD.
USNA family Waterfront Paradise just minutes from Annapolis and Baltimore, MD.
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 AED 621
AED 806 total
includes taxes & fees
10 Nov - 11 Nov
House on the Gwynns Falls
Modern Farmhouse 3Br/3.5Bth Home ☆☆Close to Johns Hopkins University &Downtown☆☆
2.0 star property
10.0 out of 10, Exceptional, (2)
Modern Farmhouse 3Br/3.5Bth Home ☆☆Close to Johns Hopkins University &Downtown☆☆
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (19)
"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
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (55)
"We had an amazing time at the house and everyone staying with us had nothing but great things to say! Would highly recommend staying here for any occasion bringing you to Annapolis!"
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is AED 727
AED 3,191 total
includes taxes & fees
11 Nov - 12 Nov
3 Story Stunner in Murray Hill <1 mile from USNA!
Luxurious, Inner Harbor Federal Hill Townhome
9.0 out of 10, Wonderful, (17)
"We had a great time during our stay, we were able to walk to many attractions and restaurants during our stay. Tia was incredibly helpful and responsive leading up to and throughout our stay. Tia’s home had everything we needed for the weekend. Finding parking outside the home could be difficult in the evening, but was easily addressed by walking, Ubering or finding a paid lot close by. "
The price is AED 856
AED 1,714 total
includes taxes & fees
10 Nov - 11 Nov
Luxurious, Inner Harbor Federal Hill Townhome
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (135)
"Joie is a wonderful host!!! Communicating with her was easy & seamless, even as she was on vacation outside the US during our stay!! We attended my 40th reunion at the Naval Academy, and this location was perfect. Easy to get to, very close to grocery stores, etc, and fully stocked!! Highly recommend to others looking to enjoy Annapolis "
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (70)
"Beautiful clean house close to Annapolis. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
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
Waterfront Home on the Chesapeake Bay!
10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!
Edgewater/Mayo Getaway!
9.8 out of 10, Exceptional, (8)
"A great property for two families with young kids to stay. Children loved the big backyard and there was plenty of space for everyone to have their own place. We loved Beverly Triton Beach and it was easy to get downtown for the Sailboat Show as well."
The price is AED 797
AED 2,073 total
includes taxes & fees
17 Nov - 18 Nov
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
10.0 out of 10, Exceptional, (90)
"Gorgeous, serene and well-appointed property! It was very comfortable for our group of four women. Highly recommend for a family or friends."
La Maison - Stunning waterfront views with pool
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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (19)
"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
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Rooftop Deck Escape! Free Parking!
9.2 out of 10, Wonderful, (22)
"Good location, close to Light Street. House was nice, enjoyed the rooftop deck with fire table. "
The price is AED 364
AED 955 total
includes taxes & fees
2 Dec - 3 Dec
Rooftop Deck Escape! Free Parking!
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.