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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Tracys Landing Vacation Homes

Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

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

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

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

10.0 out of 10, Exceptional, (113)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Relax by the pool surrounded by lush greenery and vintage bicycles.

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.2 out of 10, Wonderful, (25)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Overlooking the marina, the city skyline reflects off the calm water, offering a serene urban experience.

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $172
CA $444 total
includes taxes & fees
Aug 13 - Aug 14
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Cozy Annapolis Cottage
Relax on the outdoor deck surrounded by lush greenery and trees, featuring a sofa set, wicker chair, and small table.

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (13)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
Charming Historic Annapolis Home With Two Off-street Parking Places!
Staircase leads to a warm and inviting interior with a fireplace and wooden door.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (190)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Stroll up to the charming entrance, where a brick pathway leads to a cozy home with a red door and inviting porch.

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

9.8 out of 10, Exceptional, (45)
"Great location to the academy and shopping"
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $159
CA $429 total
includes taxes & fees
Aug 11 - Aug 12
Relax on Kent Island in 3 Bedroom Home w/Waterview
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is CA $261
CA $779 total
includes taxes & fees
Aug 18 - Aug 19
Edgewater/Mayo Gateaway w/ Hot Tub
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Enjoy a room with a sliding glass door leading to a balcony offering a water view.

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (16)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (119)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Historic Annapolis Home 1.5 blocks from center of town.
Stroll through the charming outdoor corridor to a cozy patio area with comfortable seating and a scenic view.

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (39)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.
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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Top Tracys Landing Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"The only issue was no clean up or fresh towels for the second night "
James 2-night trip
Posted 7 hours ago
DoubleTree by Hilton Hotel Annapolis