Tracys Landing Vacation Rentals from CA $322: Short-Term Rentals for 2026

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Our top choices for Tracys Landing vacation rentals

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Ellen B.

CA $482 total

includes taxes & fees

Aug 26 - Aug 27

A house with a yellow door and a window with a lamp outside.

2. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

CA $460 total

includes taxes & fees

Aug 25 - Aug 26

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Stephanie V.

CA $671 total

includes taxes & fees

Sep 8 - Sep 9

A deck with outdoor furniture, a red door, and a house with siding.

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

Joshua T.

CA $475 total

includes taxes & fees

Aug 24 - Aug 25

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."

Brian

CA $481 total

includes taxes & fees

Aug 26 - Aug 27

A lighthouse with a white exterior, a balcony, and a metal roof.

6. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Susan

CA $444 total

includes taxes & fees

Aug 20 - Aug 21

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

7. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

CA $749 total

includes taxes & fees

Sep 9 - Sep 10

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

8. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

CA $854 total

includes taxes & fees

Sep 7 - Sep 8

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

Kristin G.

CA $984 total

includes taxes & fees

Aug 20 - Aug 21

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

10. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

CA $705 total

includes taxes & fees

Aug 23 - Aug 24

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

CA $765 total

includes taxes & fees

Aug 25 - Aug 26

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

12. Plum Point Cottage #17

Huntingtown

CA $641 total

includes taxes & fees

Aug 21 - Aug 22

13. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

CA $723 total

includes taxes & fees

Sep 9 - Sep 10

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

14. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

CA $808 total

includes taxes & fees

Sep 2 - Sep 3

A swimming pool with a waterfall feature surrounded by lush greenery.

15. Waterfront Oasis of Annapolis Star

Annapolis

Thomas

CA $546 total

includes taxes & fees

Aug 20 - Aug 21

A beach with chairs and a pier in the background.

16. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Pamela B.

CA $900 total

includes taxes & fees

Aug 25 - Aug 26

A calm lake with a sandy shore, surrounded by trees and houses.

17. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

CA $1,034 total

includes taxes & fees

Aug 20 - Aug 21

A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

18. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "

rebekah h.

CA $982 total

includes taxes & fees

Aug 20 - Aug 21

19. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

CA $675 total

includes taxes & fees

Aug 20 - Aug 21

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

Cambridge

Jill C.

CA $851 total

includes taxes & fees

Sep 2 - Sep 3

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Top Tracys Landing Hotel Reviews

Comfort Inn Conference Center

10/10 Excellent

"We weren’t planning to stay overnight but the check in process was smooth and the in house restaurant was perfect!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"The location is great- not in the heart of the crowds down around the city dock, but close enough to walk down there in only a few minutes. The only negative is that the elevators were showing some grit/grime (gum stuck to the elevator floor) and the AC filter in the room was so filthy that we had to take it out and rinse it clean in the shower (not something you wanna do when you’re on your trip)."

Courtyard by Marriott Annapolis

10/10 Excellent

"We loved the quality & size of our room, the front desk folks were repeatedly helpful and very friendly and courteous. Fabulous swimming pool and hot tub area - plenty of room and the attached bathrooms with shower stalls were clean and quite useful! Wish the room had a microwave but there’s one up by the front desk so that was not a major issue. Great location with easy access to Paris Baguette, CVS Pharmacy, and the bus system is a short walk away!"

Find out more about Tracys Landing

Everything you need to know about Tracys Landing vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tracys Landing vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tracys Landing vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tracys Landing vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tracys Landing. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tracys Landing vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tracys Landing vacation rentals we have selected for you start as low as CA $322 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Tracys Landing rentals

At Expedia, we put the best Tracys Landing vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tracys Landing rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tracys Landing vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tracys Landing. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Tracys Landing?

Yes, we offer vacation rentals near the most popular attractions 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 vacation rentals in Tracys Landing?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental outside of Tracys Landing is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Tracys Landing?

With 3 Expedia vacation rentals, you're sure 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 Triton Beach. In the larger area, you’ll find Thanksgiving Farm Wines and Rod n Reel Charter Fishing.

What’s a vacation rental in Tracys Landing like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Tracys Landing. Vacation rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family gatherings.

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Check prices for these dates

Our top choices for Tracys Landing vacation rentals

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

2. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

6. Charming Coastal/Country Home w/3 Acres & Sauna!

7. Sunset Cottage - West River Access and Views!

8. 3-bedroom house in Deale located on Bay many amenities and great views

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

10. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park