Vacation rentals in Round Bay

4.96 out of 5 average rating, 408 reviews

The cottage is showcased amid a wooded setting, featuring a gravel parking area. A small covered porch is visible, accented by colorful chairs. Lush greenery surrounds the structure, and a glimpse of Mill Creek can be seen in the background.

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.

4.98 out of 5 average rating, 47 reviews

A staircase with black steps and a white railing is visible, leading to an upper level. The walls are painted light gray, complementing the wood flooring seen at the bottom. An open view into a modern kitchen can be seen in the background.

Home in Arnold

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Superhost

A vibrant sports bar setting features a large U-shaped bar with high stools, illuminated by red accents. Multiple flat-screen TVs display sporting events. A well-stocked bar is visible in the background, alongside lounge seating areas and bright overhead lighting creating an energetic atmosphere.

Guest suite in Millersville

4.83 out of 5 average rating, 150 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.

A cozy seating area features two armchairs positioned around a low table, set on a patterned rug. A brick fireplace is the focal point, with a wooden mantel displaying decorative items. A flat-screen TV is mounted above, and a bookcase is visible to the side.

4.96 out of 5 average rating, 671 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!

A spacious backyard features a pool reflecting the soft glow of lights strung along the house's back deck, creating a serene evening ambiance. The two-story home is visible in the background, illuminated alongside the surrounding greenery.

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.

4.93 out of 5 average rating, 15 reviews

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

Heron House sits on the end of a pristine point surrounded by water everywhere you look. This enchanting waterfront retreat offers the perfect blend of tranquil charm and modern comfort and has been newly furnished and remodeled. Take in the spectacular views of the Severn River on the large deck with lounge seating and dining. Only 20 minutes by boat or by car to Annapolis’ City Dock, you can enjoy charming shops, historical tours, waterfront dining, and the Naval Academy. Bring your boat!

A welcoming display is presented on a countertop, featuring a sign that reads 'Welcome to Our Home - WiFi Password.' A glass jar contains coffee creamers, alongside a box of Twinings Irish Breakfast tea and a container labeled 'Sugar.'

4.88 out of 5 average rating, 136 reviews

The Oasis - Cozy Comfort Close to Annapolis & USNA

Private first-floor guest apartment, a quiet retreat in a lovely residential neighborhood 7.5 miles to downtown Annapolis & USNA. Two bedrooms, 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.

4.9 out of 5 average rating, 290 reviews

A wooden sign displaying the name 'bean rush café' is mounted on a white fence. The café entrance is visible in the background, along with a flag displayed on the porch. Green foliage surrounds the sign, contributing to a welcoming neighborhood vibe.

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.

Superhost

A cozy living area is presented, featuring a pellet stove surrounded by a safety screen. A television is mounted on the wall, streaming content. Nearby, a wooden desk sits against the wall, with a woven basket containing blankets positioned on the floor.

Cottage in Glen Burnie

4.91 out of 5 average rating, 194 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

The spacious open-concept living area features vaulted ceilings with exposed wooden beams. A round dining table is surrounded by four upholstered chairs. A comfortable blue sofa faces a media console, while natural light streams through large windows, creating a bright and inviting environment.

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

A functional kitchen area is equipped with white cabinetry, a stainless steel dishwasher, and a microwave. Counter space is organized with utensils and kitchen appliances, including a coffee maker. The adjoining dining area is visible in the background, featuring a wooden table and chairs.

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, 50 reviews

A peaceful rooftop terrace hosts a fire pit table surrounded by a sectional sofa. The setting sun casts warm hues across the sky, reflecting on the tranquil waters of the Magothy River. Scenic views feature trees and distant buildings along the shoreline.

Houseboat in Arnold

Flohom 3 | Boho Luxe Tiny Home with 360° Views

Welcome aboard FLOHOM 3 | Bung-a-flo—a chic, Bohemian-inspired luxury tiny houseboat for two. Nestled on the tranquil waters at Ferry Point Marina, it offers picturesque views of the Magothy River and access to an award-winning seafood restaurant. Only 15 minutes from historic downtown Annapolis, MD, enjoy peaceful sunrises, stunning sunsets, and the soothing waterfront ambiance for an unforgettable escape filled with relaxation and exploration.

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Other great vacation rentals in Round Bay

Private room in Annapolis

The exterior view showcases a two-story home with a beige siding façade and large windows. A circular stone fire pit is surrounded by gravel and lawn, while comfortable seating can be seen on the patio area, framed by well-maintained gardens.

4.96 out of 5 average rating, 139 reviews

Blue Heron Room - Charming Private Room, Annapolis

AlexisRating, 5 stars2 weeks ago

Michael was responsive and friendly. he kept the house clean and, for what we needed for a short work trip, it worked out well!

A modern bathroom is showcased with sleek black and white tiles. A large mirror reflects the space, while neatly arranged white towels hang beside the sink. A stainless steel faucet sits above a square basin on a dark countertop adorned with a glass dispenser.

5 out of 5 average rating, 8 reviews

Cozy & Modern Upper Level Suite

DebraRating, 5 stars2 weeks ago

The house is in a nice quite neighborhood. The check-in was easy with the detailed instructions on how to unlock the door. The house was spotless! It is very modern and beautiful.

Private room in Annapolis

A well-lit hallway is presented, featuring light wooden floors and a soft area rug in a calming blue. On one side, a table holds decorative items and literature, while doors lead to a cozy bedroom in the background, partially visible through an open doorway.

4.96 out of 5 average rating, 338 reviews

Cape Cod Charm close to USNA & Annapolis - Room 2

UllyRating, 5 stars5 days ago

Michael and Debby's place was a gorgeous house, stylish and very comfortable. The room was cosy and I had everything I needed. Debby and Michael were lovely hosts, so helpful and friendly, and I would have spent time with them and their dog much longer ifvI didn't havd to get back on the road. And I would have enjoyed the pool if it hadn't been for the weather. An exceptional place, I would happily stay there again any time.

The living area is open and features a modern design. A dark couch faces a large flat-screen television, while a dining table with two chairs is visible nearby. A small plant adds a touch of greenery, and the space benefits from natural light.

Guest suite in Pasadena

4.75 out of 5 average rating, 8 reviews

Safe-Secured-Free Parking *Full Kitchen *Job 31:32

SalmikaRating, 5 stars2 weeks ago

Lin and Gabe were responsive, provided local recommendations, and even called from Lin’s mobile to answer a question. The neighborhood was quiet, with access to all surrounding freeways. Thank you for providing a clean, spacious relaxing unit!

The exterior of the studio apartment is displayed, featuring a vibrant red front door. The building's light gray siding contrasts with the neatly manicured red mulch landscaping. A small pathway leads to the entrance, with two decorative shrubs positioned at the front.

Apartment in Glen Burnie

4.8 out of 5 average rating, 116 reviews

♥︎Private Cozy Studio Apartment minutes From BWI♥︎

CaitlynRating, 5 stars5 days ago

Cute one bedroom with small kitchenette, pet friendly so that’s a plus if you’re traveling with your fur babies. Large refrigerator and wall AC unit. I wouldn’t recommend more than two people or it will be cramped, but it’s good for one person or a short stay. Note that it is directly off a main road that seems to be a common emergency vehicle route, so it can be noisy.

5 out of 5 average rating, 6 reviews

A cozy corner features a modern fireplace with a unique arch design, framed by large windows that allow natural light to brighten the space. A decorative compass rose is mounted above the fireplace, alongside a subtle display of indoor greenery.

Home in Severna Park

Sunset Heaven on the Severn

JoshRating, 5 stars2 weeks 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!

5 out of 5 average rating, 6 reviews

A swing hangs from a sturdy tree branch in a grassy area, providing a relaxing spot to enjoy the outdoors. Nearby, a circular stone firepit is surrounded by two outdoor chairs, creating a cozy setting for evenings around the fire.

Home in Odenton

Train Tracks Getaway

MichaelRating, 5 stars1 week ago

we were in town for a family gathering and the house was exactly what we were looking for.