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Tracys Landing Holiday Rentals

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Holiday Rentals in Tracys Landing

Historic Row Home in Downtown Annapolis

The price is AU$951
includes taxes & fees
22 July - 23 July
Historic Row Home in Downtown Annapolis

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is AU$976
includes taxes & fees
22 July - 23 July
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is AU$1,198
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

❤️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 AU$542
includes taxes & fees
3 Aug - 4 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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 AU$477
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is AU$2,151
includes taxes & fees
28 July - 29 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,086
includes taxes & fees
21 July - 22 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is AU$802
includes taxes & fees
21 July - 22 July
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (2)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is AU$790
includes taxes & fees
21 July - 22 July
Charming Pet-Friendly Stay - Near Bay & Beaches.

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$741
includes taxes & fees
27 July - 28 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is AU$1,291
includes taxes & fees
22 July - 23 July
Charming Annapolis WaterVIEW Home

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$1,286
includes taxes & fees
21 July - 22 July
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$766
includes taxes & fees
20 July - 21 July
Neptune by the Water

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is AU$963
includes taxes & fees
29 July - 30 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AU$996
includes taxes & fees
5 Aug - 6 Aug
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is AU$738
includes taxes & fees
20 July - 21 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$701
includes taxes & fees
28 July - 29 July
The Cottage

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (7)
"Beautiful house in a great location to Main Street Annapolis. "
The price is AU$1,413
includes taxes & fees
23 July - 24 July
USNA Luxury Home, parking, pet friendly

Historic Row Home 1 Block from Gate 1 at USNA!

The price is AU$1,142
includes taxes & fees
31 July - 1 Aug
Historic Row Home 1 Block from Gate 1 at USNA!

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"We loved our stay! The property is lovely, well appointed and couldn’t be in a better location! We can’t wait to come back!"
The price is AU$1,004
includes taxes & fees
21 July - 22 July
Freshly renovated 3-story home 1 block from USNA!
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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Frequently asked questions

Can I find holiday rentals in Tracys Landing?

Yes, there are holiday rentals close to the most popular sights in Tracys Landing, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tracys Landing has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Tracys Landing is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Tracys Landing?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Tracys Landing stay.

What’s there to see and do in Tracys Landing?

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Shadyside Park. In the wider area, you’ll find Bayside History Museum and Rod n Reel Charter Fishing.

What’s a holiday rental in Tracys Landing like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Tracys Landing. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.