Photo by Mary Pat Collins

Tracys Landing Holiday Rentals

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Holiday Rentals in Tracys Landing

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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, (18)
"We had a great stay at the Turning Point! We had a great time playing Cornhole, pickleball, basketball, cooking on the grill, cooling off in the pool, and watching football on the big screen TV. House was very clean and comfortable. Would definitely stay again and would highly recommend it to anyone."
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, (213)
"I thoroughly enjoyed my stay at this quiet, peaceful cottage on Harris Creek. The house is very clean and inviting, and stocked with just about anything you would need. This was my second time here, and I'm already planning a trip back next year. The fishing was awesome! It's a great place to be if you're a birdwatcher. The Black Water Wildlife Refuge is only an hours drive away. St. Michaels is less than 15 minutes up the road where you'll find restaurants, grocery stores, and lots of quaint...
Relaxing Waterfront Cottage Near St Michaels, Maryland
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (199)
"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
Outdoor dining
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
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, (199)
"Couples getaway weekend to Annapolis. This was the perfect place to have our Basecamp. Absolutely beautiful location, quiet, and peaceful and easy to get everywhere!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cottage on the Eastern Shore
Interior
Waterfront Cottage on the Eastern Shore
8.6 out of 10, Excellent, (8)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AU$1,198
includes taxes & fees
6 Oct - 7 Oct
Waterfront Cottage on the Eastern Shore
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is AU$1,419
includes taxes & fees
15 Oct - 16 Oct
3 Story Stunner in Murray Hill <1 mile from USNA!
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
9.4 out of 10, Exceptional, (10)
"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
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (52)
"We had a wonderful stay at this beautiful home! Our Navy football weekend could not have been better. This is the perfect place for eight people to gather. The home is spotless and we all appreciated having such a nice place to relax and visit for the weekend. We really enjoyed the spacious and comfortable backyard seating as well as the kitchen/living room spaces. Being able to walk to the stadium for the game and into town for shopping and dining was a real plus. It was a pleasure dealing...
Recently Renovated Annapolis Home - Conveniently Located
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Charming Cottage with Hot Tub 1 Block from the Bay
Terrace/patio
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (7)
"Great property. Close to USNA but away from the craziness of town. House was adorable and very clean. The hot tub was a big hit. "
The price is AU$891
includes taxes & fees
7 Oct - 8 Oct
Charming Cottage with Hot Tub 1 Block from the Bay
Walk to Everything House
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, (70)
"This home was the perfect place for us to stay. Check-in was easy. The home was clean and well-furnished with lots of space for our family. We loved the four-poster beds. There is a lovely table and chairs to sit outside. The location is convenient for walking downtown to many shops and restaurants."
Walk to Everything House
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, (32)
"Jacob’s home was perfect for our wedding weekend. It had plenty of space for all of our family members. There was more than enough space throughout the house and outside for all of us to relax and enjoy time in. The view of the water is amazing! Hope to come back another time, thank you!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (150)
"The Yellow Cottage was a perfect spot for my daughter and I to spend the weekend near Annapolis. The location was perfect, near the city but also very close to a delightful winery. Everything was provided which means you can pack lightly. We unfortunately did not have the opportunity to hit the water on this trip. "
The Yellow Cottage on Harness Creek
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (105)
"The only downside and it was miniscule in relation to the overall experience was the amount of debris on the front porch that came from storms blowing off of the trees. Couldn't really be helped and again very minor issue. The rest of the house was fabulous!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (27)
"A most comfortable rental! Clean, roomy, and a well equipped kitchen. TV…all the channels you could ever want.. a great rental!!"
The price is AU$410
includes taxes & fees
16 Oct - 17 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (37)
"We’ve stayed in every hotel in Annapolis and have been a regular visitor to The City every Labor Day for a decade. Somehow we always make it to Eastport and love the smaller crowds, restaurants and bars. Finding this spot was perfect for us. Clean, updated and comfortable. If you just need a base of operations for a few days we’d recommend Sandra and her property! Awesome location close to everything we wanted. "
Anchor's Away in the Heart of Eastport!
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Other types of properties in Tracys Landing you may be interested in

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, (1379)
"The staff were very accommodating and helpful.. it’s always a pleasure staying here. Thanks again for the great service "
The price is AU$133
includes taxes & fees
8 Oct - 9 Oct
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1665)
"good stay"
The price is AU$285
includes taxes & fees
27 Oct - 28 Oct
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (999)
"I used this hotel as our stay hotel for my boys who shipped to bootcamp. It is across from the Annapolis mall and has restaurants in walking distance. The rooms are beautiful and spacious."
The price is AU$173
includes taxes & fees
22 Oct - 23 Oct
Crowne Plaza Annapolis, an IHG Hotel
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.

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?

Rockhold Creek Cottage, Water Front, Vacation Home, Docks: This holiday home rental outside of Tracys Landing is located on a river, and has a balcony, a garden 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 Show Place Arena.

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.