Vacation rentals in Tracys Landing

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Top-rated vacation rentals in Tracys Landing

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Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 118 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Nov 30 – Dec 7

G$109,647 GYD per night

Guest favorite

Apartment in North Beach

4.96 out of 5 average rating, 103 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Oct 21 – 28

G$27,836 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 314 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Sep 1 – 8

G$31,930 GYD per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 209 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Dec 16 – 23

G$20,458 GYD per night

Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Oct 22 – 29

G$37,577 GYD per night

Guest favorite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 104 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Jul 18 – 25

G$20,072 GYD per night

Guest favorite

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Bring your own boat! Make wonderful memories. Great place for families and multi family groups.

Oct 10 – 17

G$113,971 GYD per night

Guest favorite

Apartment in Deale

4.91 out of 5 average rating, 614 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Apr 29 – May 6

G$45,325 GYD per night

Guest favorite

Home in Deale

4.99 out of 5 average rating, 125 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Aug 5 – 12

G$48,987 GYD per night

Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

Dec 15 – 22

G$96,042 GYD per night

Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 273 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Aug 11 – 18

G$51,080 GYD per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

Jul 30 – Aug 6

G$25,375 GYD per night