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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.

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

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.

Waterfront farm retreat for vacation & telework

Stay on 125-acre Hollywood Farm in a beautiful and quiet home surrounded by water and woods. Our airy, mid-century renovated cottage feels like a sanctuary, tucked away on a peninsula on one of the largest tracts of conservation land in Maryland. This cozy, light-filled space is small but spacious, allowing you to work peacefully from home with a full desk and excellent high-speed internet access. Plus, there's a dock, kayaks, and lots of outdoor space for children and pets to run around in.

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Gorgeous Historic Downtown Annapolis House

USNA grad-owned, this 5 bedroom & 3.5 bathroom elegant house is located in the heart of downtown Annapolis (1 block from USNA Gate 3 & from St. John's College). Cable, WIFI, linens, towels, and a parking pass for one car included (street parking only). Pet requests considered (permission required in advance; there is a $500 pet fee if approved). Beautiful backyard for entertaining. We ask guests to treat the space as if they are guests in our home. We look forward to hosting you!

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

Pet-Friendly King Suite + Kitchen | Near Annapolis

Settle in just minutes from Annapolis in a spacious, pet-friendly guest suite with a king bed, full kitchen, separate living area, and year-round hot tub access. Perfect for couples, families, pet owners, and longer stays, Captain's Quarters sleeps up to 4 with a king bed plus a queen-size LoveSac sofa bed. Located just 4 miles from historic Downtown Annapolis and the U.S. Naval Academy, with private keyless entry, fast Wi-Fi, designated parking, and all the comforts of home.

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

Garden View, 1 Bedroom and a 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.

Waterfront CHeerful 2 with Private home

Welcome to this relaxing home by the water for your getaway. It is perfect for vacations, retreats, meetings, family visits, and BUSINESS travelers. One level home has two bedrooms and 2 1/2 full bathrooms, two walk-in showers, a breakfast room, a kitchen, Family room. The house entrance has no step One Queen bed and one king bed