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

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Calloway Drive Retreat | House in Shady Side

9.2 out of 10, Wonderful, (5)
"We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier."
Calloway Drive Retreat | House in Shady Side

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

Private Waterfront Woods | Dock, Kayaks, Views

9.8 out of 10, Exceptional, (15)
"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

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, (72)
"House is exceptionally clean. Hosts are very responsive to questions. House is very well supplied and convenient to most of Annapolis. House is as advertised. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (13)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (3)
"From communication to check-in and cleanliness, this VRBO has plenty of room and modern amenities. What put this over the top was that a party member left the wallet at the VRBO, and the renters went and retrieved the wallet and met us to return it. They went above and beyond to help us. It has a good backyard and can park 3-4 cars in the driveway; this VRBO has everything. Easily five stars"
Brand New Spacious Luxury Home

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (31)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is HK$645
HK$2,027 total
includes taxes & fees
5 Jan - 6 Jan 2025
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

10.0 out of 10, Exceptional, (102)
"Awesome House Awesome neighborhood Awesome Host(ess). 10 out of 10"
The price is HK$3,110
HK$4,033 total
includes taxes & fees
12 Jan - 13 Jan 2025
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Walk to Everything House

10.0 out of 10, Exceptional, (74)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (27)
"Felt like home as soon as we walked in...except it was CLEANER than home :-) Comfortable, spacious, well-stocked. Hosts were attentive & quick to answer messages. Great experience!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (12)
"Great place, wonderful location "
Bennett House (entire):Haven in Historic Annapolis

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (29)
"We loved our weekend here! The house was just as described. Location was perfect to be able to walk to everything downtown, yet far enough away that it was quiet. Loved the charm of the house, bed was very comfortable, and it had everything we needed. We would definitely return! "
Historic Annapolis Home 1.5 blocks from center of town.

Serene waterfront sunsets in this sprawling historic Annapolis home

9.8 out of 10, Exceptional, (27)
"We had such a wonderful Father’s Day weekend, at this lovely property! The views are beautiful, the house was laid out perfectly for our large family, and everyone enjoyed fishing off the dock."
Serene waterfront sunsets in this sprawling historic Annapolis home

Private Waterfront Retreat with Pool, Hot Tub and Game Room

10.0 out of 10, Exceptional, (23)
"The home was wonderful! So clean and spacious! Very modern beachhouse style home with an amazing view. We loved waking up every morning to see the sunrise. Host was very accommodating and professional. 5/5! Highly recommend this property!"
Private Waterfront Retreat with Pool, Hot Tub and Game Room

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (4)
"We stayed here for four days over July 4th holiday. The house is clean, modern, updated and looked new on the inside. Well equipped with linens, towels, bath products, appliances and accessories. Conveniently located to Herrington Harbor marina for events and weddings. Huge fenced backyard which was great for kids and pets to run around. There were a couple of minor issues with the AC (due to a storm power outage) and the guests before us also didn’t take out their trash so the can was full. But...
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Pet-Friendly Annapolis Home: Walk to Beach!

10.0 out of 10, Exceptional, (5)
"I took my family down for the weekend to see the Navy football game. The house was perfect and as described. The outside space was just as nice as inside and the neighbors were friendly too. We will absolutely rent here again. "
Pet-Friendly Annapolis Home: Walk to Beach!
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!

10.0 out of 10, Exceptional, (205)
"A great experience all around"
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, (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

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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.