Pet-friendly vacation rentals in Parole

4.96 out of 5 average rating, 420 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

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.

4.94 out of 5 average rating, 413 reviews

A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.

Condo in Annapolis

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens, lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 10.

5 out of 5 average rating, 184 reviews

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

A charming single-story house is presented with a light gray exterior and a prominent teal door. Symmetrical landscaping frames the entrance, featuring neatly trimmed hedges and colorful plants. A concrete pathway leads to the front steps, inviting guests into a welcoming atmosphere.

4.94 out of 5 average rating, 106 reviews

Charming Annapolis Retreat with Hidden Wine Room

Discover charm in our 2BR, 1BA Eastport home, just a stroll away from downtown Eastport (under 1 mile), Downtown Annapolis (1.3 miles), the Naval Academy (2.3 miles), and less than 3 miles to Navy Stadium. Relax on our screened porch, by the fire pit, or under the cozy cabana out back. Delight in a secret—a hidden wine cellar awaits below! Plenty of free parking under the carport or on the street. Plus, with the water taxi service at the nearby dock, the best of Annapolis is just a call away.

The open-concept living space features hardwood floors and large windows allowing natural light. A neutral-colored sofa with side cushions is positioned near a coffee table. A dining table accommodates multiple guests, while the kitchen showcases modern appliances and cabinetry.

4.99 out of 5 average rating, 117 reviews

Charming Downtwn Home- Private Parking Patio&Yard!

Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you!

4.87 out of 5 average rating, 106 reviews

The bedroom features a plush queen bed dressed in neutral linens, complemented by two bedside lamps and coastal-themed artwork. A cozy sitting area includes a light blue armchair and a small table. Ample storage is provided by a closet with sliding doors.

Guesthouse in Annapolis

Cozy Retreat w/Private Beach Access

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

Guesthouse in Stevensville

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

4.99 out of 5 average rating, 303 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

A cozy living room features a large sectional sofa adorned with soft pillows. A coffee table sits in the center on a vibrant area rug. A television is positioned on a side table, with natural light coming through the windows. The entrance door adds warmth to the space.

4.93 out of 5 average rating, 187 reviews

Chesapeake Comfort, Annapolis.

Veteran Superhost! Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with my listings for over 5 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town.There is a kayak/paddle launch at the bottom of the street. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch.

Guesthouse in Glen Burnie

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

4.93 out of 5 average rating, 358 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

4.99 out of 5 average rating, 143 reviews

A spacious backyard features a hammock strung between two trees and a stone fire pit surrounded by seating. Nearby, a propane grill and a stack of firewood are arranged on a grassy lawn, offering a relaxed outdoor setting.

Guesthouse in Annapolis

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

4.94 out of 5 average rating, 182 reviews

A spacious outdoor area features a clear swimming pool with a shaded gazebo nearby. Four lounge chairs are positioned around the pool, complemented by a small side table. Lush greenery surrounds the space, providing a peaceful atmosphere.

Guest suite in Arnold

Pet Friendly Captains Quarters, Near Annapolis, EV

Our pool is closed for the season; however, our hot tub is open! This space has been fully updated with all the conveniences and amenities to make your stay enjoyable! We offer: - a king bed, - a queen bed sleeper sofa, - high speed internet, - a furnished kitchen, - private en-suite bathroom, and - a coffee bar. We're close to everything - located four miles from my hometown Annapolis!

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.