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Compare 489 Vacation Homes in Tracys Landing with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (73)
"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

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

9.8 out of 10, Exceptional, (38)
"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

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

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

10.0 out of 10, Exceptional, (206)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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 SAR 556
SAR 2,393 total
includes taxes & fees
12 Jan - 13 Jan
Freshly renovated 3-story home 1 block from USNA!

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"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

9.6 out of 10, Exceptional, (18)
"This property worked well for our large family. Most houses that sleep larger numbers don't come with a kitchen stocked for corresponding large numbers. But this kitchen was very well stocked with plenty of dishes and larger pots/pans for larger groups. "
Private Waterfront Woods | Dock, Kayaks, Views

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (62)
"Perfect location. Close to the big cities but far enough away to relax. Lots of shopping close by. Very clean. Trent is an excellent communicator. We highly recommend and will definitely consider staying here again in the future. We picked it because I grew up in Crofton and my mom lives close by. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is SAR 193
SAR 833 total
includes taxes & fees
13 Jan - 14 Jan
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

10.0 out of 10, Exceptional, (14)
"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (33)
"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 SAR 193
SAR 833 total
includes taxes & fees
13 Jan - 14 Jan
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (41)
"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...
The Lazy Crab Beach House - Free beach passes

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

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.

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

9.8 out of 10, Exceptional, (28)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

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

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

Serene waterfront sunsets in this sprawling historic Annapolis home

9.6 out of 10, Exceptional, (28)
"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

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

10.0 out of 10, Exceptional, (5)
"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!
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 Tracys Landing

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

9.8 out of 10, Exceptional, (38)
"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

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

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