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Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool, gym, sauna, and a massive family room with 10 ft ceilings, and a 67 " Smart TV. Enjoy the large 1st class chef's kitchen with all the cooking & serving supplies you will ever need. Enjoy the modern amenities, multiple workspaces, a wrap-around porch, a fire pit, & a grill. Ideal for family events, quiet getaways, sports teams, & business meetings. You are able to have your l

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Pool House -No Contact 24/7 Self Check-In- Private

Secluded Tiny Guest House Retreat with Private Pool – Near Baltimore & Annapolis As you pull into the driveway, the city noise melts away—replaced by the serenity of trees and the inviting sparkle of your private in-ground swimming pool. This 320 sq. ft. Pool House is cozy. A large window fills the space with natural light to the ever-changing views of the wooded setting. Completely private stay – no shared spaces Self check-in with no contact Private pool exclusively yours during your stay

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. You’re renting a private ground-level guest suite with separate entrances. Inside you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces).

1 bedroom -king in Annapolis- low cleaning fee

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*

“Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, outdoor 6-person hot tub, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. * Best Places To Stay Annapolis*Ice Skating

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Coastal Comfort Retreat near Annapolis, EV charger

*New hot tub and pergola installed!* Escape to a cozy, modern retreat just 4 miles from downtown Annapolis. This intimate king suite offers a private seating area, kitchenette, & TV. The ensuite bathroom features a luxurious shower. Relax in peace and comfort after exploring Annapolis or attending local events. Please note that the pool and hot tub are closed for the season. Reach out anytime with questions or special requests—we’re happy to help make your stay memorable!

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.