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Tracys Landing Holiday Rentals

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Holiday Rentals in Tracys Landing

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)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
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)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
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, (217)
"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
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
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, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,349
includes taxes & fees
2 Dec - 3 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

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

9.8 out of 10, Exceptional, (35)
"We had a wonderful time with beautiful views at this property. There's no better way to celebrate a special birthday in the comfort and luxury of this waterfront property in MD! Will definitely consider again for future. "
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$365
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in 3 Bedroom Home w/Waterview
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
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (100)
"We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
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)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (71)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AU$689
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
USNA Quintessential Charm ~ Downtown Annapolis.
Fridge, microwave, oven, stovetop

USNA Quintessential Charm ~ Downtown Annapolis.

9.8 out of 10, Exceptional, (6)
"We really enjoyed this property. It was clean and tidy. Checking in was simple. Parking was straightforward once we noticed the markers giving us clear instructions. The kitchen has everything you need. I stayed in the downstairs bedroom, and the bed and pillows were very comfortable. The downstairs shower is small, but the water pressure is good. Everyone who stayed upstairs enjoyed the amenities. Definitely will try to rent this again for the next time we visit Annapolis."
USNA Quintessential Charm ~ Downtown Annapolis.
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (136)
"My family and I love staying here! It's clean, beautiful, spacious, and comfortable. It's home away from home. I love all the special touches--lots of cozy blankets, the beautiful decor, the comfortable beds. And, of course, it's close to anything you want to do in Annapolis or the surrounding areas. During this stay, we were able to enjoy the patio, which was especially wonderful to be able to do in November. My favorite spot is the sitting area next to the kitchen; it's a perfect place to...
Your Annapolis Adventure Starts Here!!
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (38)
"The Lazy Crab was such a delightful home to visit. The kitchen was fully stocked and the house had everything any traveler could need, including a washer and dryer! It was evident that the owners put a lot of love into making sure guests enjoyed their stay. I highly recommend! You will feel right at home."
The Lazy Crab Beach House - Free beach passes
Mid-Century Modern and Marvelous on the Bay
Property grounds

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
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 types of properties in Tracys Landing you may be interested in

Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1831)
"My husband and I stayed at the Governor Calvert House for 3 nights. We were able to book an extra night and were even able to check in earlier, with no fee, if we wanted! The staff was friendly, the Inn was ADORABLE, and we loved how accessible it was to everything. Truly felt like a Hallmark movie experience. The only negatives that we had were that there were no microwaves accessible to guests - none in the room or lobby, and no laundry facility. These are minor inconveniences, but still...
The price is AU$246
includes taxes & fees
23 Dec - 24 Dec
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Exterior

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

2.5 star property
6.4 out of 10, (1549)
"Perfect "
The price is AU$162
includes taxes & fees
17 Dec - 18 Dec
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
La Quinta Inn by Wyndham Waldorf
Exterior

La Quinta Inn by Wyndham Waldorf

2.5 star property
7.4 out of 10, Good, (971)
"Very confortable place "
The price is AU$135
includes taxes & fees
12 Dec - 13 Dec
La Quinta Inn by Wyndham Waldorf
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 Breezy Point Beach. In the wider area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

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.