Holiday Homes in Shady Side

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Featured Holiday Homes in Shady Side

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous
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!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property
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
Property grounds
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.8 out of 10, Exceptional, (59)
"All positives, no negatives. We hope to stay in this beautiful home again!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop
Bay views with kayaks, bikes, fire pit, crabbing and more
9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
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
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (56)
"This house is so cute and comfortable. Everything was perfect and better than described. It is within walking distance of some delicious restaurants. Our host was amazing and answered all questions very quickly."
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!
Terrace/patio
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (17)
"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 AU$1,359
includes taxes & fees
18 Nov - 19 Nov
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop
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.
Exterior
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
Property grounds
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
Fridge, microwave, oven, stovetop
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!
Fridge, microwave, oven, stovetop
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!
Fridge, microwave, oven, stovetop
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 AU$905
includes taxes & fees
17 Nov - 18 Nov
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
Miscellaneous
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
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Terrace/patio
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
8.8 out of 10, Excellent, (19)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Point of interest
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
10.0 out of 10, Exceptional, (16)
"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Charming Annapolis WaterVIEW Home
Outdoor dining
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop
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
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (32)
"We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (106)
"We were in town for a sailing event and the house was in a perfect location for us. "
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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 Shady Side

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous
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
Fridge, microwave, oven, stovetop
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
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
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.