Holiday houses in Round Bay

4.96 out of 5 average rating, 408 reviews

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Superhost

Guest suite in Millersville

4.83 out of 5 average rating, 148 reviews

The Lower Level Loft near BWI

Unwind in this tranquil, stylish in-law suite, updated for your comfort. Located on the lower level of a townhouse just minutes from BWI, this space offers a private entrance.Inside, you'll find an inviting dining area, a spacious bathroom, and a cozy bedroom featuring a brand-new queen-sized bed and a high-definition TV. There are two dedicated parking spaces that are well-lit. The kitchenette has a fridge, microwave, coffee maker, etc., providing all the essentials for a comfortable stay.

4.96 out of 5 average rating, 669 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!

4.94 out of 5 average rating, 176 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. 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.

4.9 out of 5 average rating, 288 reviews

Guesthouse in Annapolis

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.

4.87 out of 5 average rating, 135 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Private first-floor guest apartment, a quiet retreat in a lovely residential neighborhood close to downtown Annapolis. It has 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. It’s ideal for travelers who want privacy, and a little more space than the usual stay. Sip your morning coffee in the gazebo and unwind after day trips fireside on the comfy sectional. The kitchen is ideal for enjoying light cooking or take outs. Comfy queen sized beds with crisp linens.

Superhost

Cottage in Glen Burnie

4.91 out of 5 average rating, 191 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.

Apartment in Severna Park

5 out of 5 average rating, 60 reviews

Welcome to Anchors Aweigh!

Kick back and relax in this calm, newly remodeled, stylish space. "Anchors Aweigh" provides a peaceful getaway in a quiet community with a water view of Cattail Creek. The first floor game room is stocked with games for your entertainment and competitive streak ;) Upstairs you'll find a large spacious living room, kitchen, full bathroom and bedroom, where you can unwind after a long day of sightseeing. *guests are not permitted use of waterfront activities, for liability.

Guesthouse in Severna Park

4.98 out of 5 average rating, 83 reviews

Private Severn Riverfront Guest Cottage

Tranquil, relaxing guest cottage faces the Severn River. Downtown Annapolis is 15 minutes by car; Baltimore, 30 minutes; and Washington, DC, 50 minutes. Crabbing, swimming, fishing available at area parks. Quiet walking neighborhood along river with easy access to Maryland Route 2, US Route 50, BWI airport and the Baltimore-Annapolis bike trail. Beautiful views, access to yard and gardens, herbs and tomatoes at your doorstep in summer. Queen bed-2 adults; 2 cots-children.

4.98 out of 5 average rating, 617 reviews

Guest suite in Pasadena

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 343 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

Guest suite in Severna Park

4.98 out of 5 average rating, 58 reviews

Waterfront Apt Near Annapolis -Boat Slip available

This waterfront apartment features a beachy style with amazing views of the Magothy River. Hang out on the dock or backyard sitting areas. Curl up with a book, play a game or lounge on the sofa and watch TV in this comfortable, clean and private apartment close to Annapolis. Use our kayaks or paddle board on the river or bring your own boat to use while you stay. Guest slip accommodates most boats up to a 23' boat.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Round Bay holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Round Bay

5 out of 5 average rating, 7 reviews

Cozy & Modern Upper Level Suite

LoriRating, 5 stars1 month ago

I’ve stayed in a lot of Airbnb properties and Whytnie’s is one of the cleanest and best maintained I have ever seen. The bed was comfortable as was the furniture and the kitchen was well equipped. I sat out on the deck one evening which was pleasant and there is a large backyard that kids could run around in. Whytnie responded quickly to a kitchen question I had and that was super helpful. We would definitely stay there again as the location worked well for our needs.

Private room in Annapolis

4.96 out of 5 average rating, 336 reviews

Cape Cod Charm close to USNA & Annapolis - Room 2

JoeRating, 5 stars1 week ago

Beautifully decorated space, super clean, great location, and wonderful stay overall.

5 out of 5 average rating, 6 reviews

Home in Severna Park

Sunset Heaven on the Severn

JoshRating, 5 stars1 week ago

Ann has a jewel of a property, and is a kind and thoughtful host. The house has a private “beach” and 180 degree views of the cove off the Severn River, and you can spend endless hours watching a nesting Osprey couple take care of their chicks. Ann offers several lovely personal touches such as a garden filled with sugar peas, arugula and lettuce that you are encouraged to enjoy. The primary bedroom has an insanely nice view of the water and the ospreys, and a very comfortable bed. And the house has fun art and artifacts from her travels both local and abroad. What a great stay! Thank you, Ann!

4.95 out of 5 average rating, 93 reviews

Guest suite in Annapolis

Annapolis Garden Suite

JensenRating, 5 stars1 week ago

Laura was very accommodating and we enjoyed staying in her space! Excellent, wonderful communication was a giant plus for us. We are grateful that Laura stayed in touch with us during some mishaps that were not at all related to her or her cleaning team. Thank you.

Cottage in Severna Park

4.76 out of 5 average rating, 25 reviews

Colorful Round Bay Cottage

AsitaRating, 5 stars5 days ago

We usually book AirBnBs for the kids to have fun but they loved how cozy this cottage was. It had such a home feel, felt warm and inviting. The hosts were very nice and responsive as well.

5 out of 5 average rating, 15 reviews

Barn in Davidsonville

1bd 1 ba detached guest loft

CharlesRating, 5 stars1 week ago

Mary was an excellent host. Any question I had she responded in great time. Mary's place is set up great. Had everything you need. Super peaceful and quiet. Would stayed longer if I could have. Recommend to anyone.

Home in Severna Park

5 out of 5 average rating, 5 reviews

Gorgeous Architectural Home - USNA Commissioning

PatrickRating, 5 stars24 months ago

Beautiful home close to the U.S. Naval Academy and Annapolis, MD.