Vacation rentals in Pooles Island

* Beautiful Oasis w/ No Detail Spared

Kick back and relax in this calm, stylish space! No details were spared in the latest renovation to Maura & Pete's Airbnb properties. From the moment you walk in you will be overwhelmed with the tremendous comfort in the living room leading to a kitchen well equipped with your cooking needs. Along the way there is a washer & dryer if needed. Upstairs you will find a gorgeous bathroom right next to a perfectly laid out bedroom w/ plush king bed where you can watch your favorite show on the HD TV!

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Waterfront Romantic Studio

Unwind at our private studio getaway-featuring an updated kitchen & bathroom, and cozy sleeping area. Separate entrance for complete privacy. Step out onto the shared deck and take in stunning water views, perfect for your morning coffee or a relaxing evening drink enjoy the waterfront vibe. Make memories around the fire pit or explore nearby state parks with scenic hiking trails and beaches. Whether you’re here for a show, a convention, or just some sightseeing, only 20 minutes from Baltimore.

Gorgeous Studio Apt. In Historic Chapel w/ Parking

This stunning private studio rivals Baltimore’s top hotels and is packed with premium amenities most Airbnbs don’t offer. Once a mystery church set for demolition, it’s now a fully renovated mid-century modern gem with private access, a fully stocked kitchenette, new hardwood floors, and a luxe stone tile rain shower. Sleep soundly with down feather bedding, enjoy luxury toiletries, a 55” smart TV, and courtyard views through gorgeous French doors—all in a prime location with easy, free parking

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Watch Deer from a Farm Cottage

Farm Animals, Wildlife, Country Living close to all conveniences. Located within 5 minutes of I-95 in Bel Air, Maryland in an upscale neighborhood, within walking distance to Cedar Lane Sports Complex and short drive to Hospitals, Restaurants, Theatres etc. Quaint, freshly cleaned & sanitized interior amenities like Comfort Grande Beds, Egyptian cotton linens, ultra quiet HVAC and other features of a quality home in a modest exterior awaits you in this primitive gentleman's farm setting.

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Historic Bank Fells Point

A spectacular marble columned facade of the former Polish Bank invites you to enter this apartment designed with mid century modern furniture . The 800 square foot 2nd floor apartment features original vaulted ceilings and columned walls from the 1800s and many of the original features from its former life as a bank, all the while blending modern furniture to create a hip vintage vibe.