Vacation rentals in Round Bay

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Top-rated vacation rentals in Round Bay

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Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 550 reviews

Sea Dreamer aka Phenomenal Hospitality

Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.

Apr 10 – 17

G$19,678 GYD per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 569 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul 18 – 25

G$23,362 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 316 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!

Oct 6 – 13

G$31,265 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.

Mar 24 – 31

G$20,421 GYD per night

Guest favorite

Cottage in Glen Burnie

4.92 out of 5 average rating, 143 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Nov 21 – 28

G$16,744 GYD per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 157 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Nov 16 – 23

G$29,135 GYD per night

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 199 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Jul 9 – 16

G$29,999 GYD per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 166 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

Oct 21 – 28

G$19,384 GYD per night

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 118 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Jul 26 – Aug 2

G$36,529 GYD per night

Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 264 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Aug 29 – Sep 5

G$48,658 GYD per night

Guest favorite

Guest suite in Edgewater

4.89 out of 5 average rating, 441 reviews

South River Park Apartment

Located minutes from Annapolis, MD the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Feb 2 – 9

G$20,816 GYD per night

Guest favorite

Cabin in Gambrills

4.89 out of 5 average rating, 141 reviews

Relaxing Cabin Get Away Near Annapolis & DC

This is a 1,000 sq foot open concept rustic cabin. There are 4 "rooms" including a fully equipped kitchen, a dining room, a family room with a TV for movies and streaming, and a bedroom full of windows. It is located down a 1/3 mile gravel driveway in the woods on 72 acres of land that has been dedicated in perpetuity to not being developed.

Aug 10 – 17

G$31,033 GYD per night