A calm lake with a boat in the distance, surrounded by dense forest.

Tracys Landing Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $98
CA $445 total
includes taxes & fees
Oct 6 - Oct 7
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

2. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $326
CA $683 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!
A house with a yellow door and a window with a lamp outside.

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

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $186
CA $472 total
includes taxes & fees
Oct 8 - Oct 9
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A market with a covered seating area and a sign indicating parking for curbside pickup.

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is CA $321
CA $619 total
includes taxes & fees
Oct 5 - Oct 6
Rose Haven Coastal Cottage
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is CA $262
CA $740 total
includes taxes & fees
Oct 14 - Oct 15
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

6. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $310
CA $716 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $244
CA $541 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

8. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $437
CA $645 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $416
CA $1,101 total
includes taxes & fees
Oct 26 - Oct 27
Family Home on Mayo Peninsula | Deck | Sleeps 10
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is CA $324
CA $866 total
includes taxes & fees
Oct 20 - Oct 21
Renovated Bungalow | Walk to Beach | Dog-Friendly
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $126
CA $409 total
includes taxes & fees
Oct 5 - Oct 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beach with chairs and a pier in the background.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $328
CA $752 total
includes taxes & fees
Oct 20 - Oct 21
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Pool

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $205
CA $653 total
includes taxes & fees
Oct 6 - Oct 7
Family Beach House: Spacious Deck, Grill & Views
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.

14. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"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. "
United States
rebekah h.
The price is CA $345
CA $994 total
includes taxes & fees
Oct 5 - Oct 6
Londontowne Rancher | 3BR | Near Waterfront
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $243
CA $683 total
includes taxes & fees
Nov 1 - Nov 2
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

16. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $242
CA $411 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

17. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is CA $298
CA $822 total
includes taxes & fees
Nov 4 - Nov 5
Annapolis Retreat - 7 mins from downtown Annapolis!
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

18. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $388
CA $658 total
includes taxes & fees
Oct 5 - Oct 6
Plum Point Cottage #17
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $152
CA $443 total
includes taxes & fees
Oct 7 - Oct 8
Charming Coastal/Country Home w/3 Acres & Sauna!
A hotel entrance with a stone facade, a covered entrance area, and a central light fixture.

20. Top Location | Free Breakfast + Fitness Center

Top Location | Free Breakfast + Fitness Center
Lanham
10.0 out of 10, Exceptional, (2 reviews)
"Very nice!"
United States
Kerry B.
The price is CA $186
CA $242 total
includes taxes & fees
Oct 25 - Oct 26
Top Location | Free Breakfast + Fitness Center
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great Hotel in a very central location"
Mark 2-night trip
Posted 1 hour ago
Graduate by Hilton Annapolis

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 $242 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 Breezy Point Beach. In the larger area, you’ll find Bayside History Museum and Thanksgiving Farm Wines.

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.