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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.

Secluded Tiny House With your own Private Pool

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

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.

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property should extra toilets and showers be needed from April-November only.

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.

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

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!

Waterfront GEM - HUGE HOME for FAM/WORK/FUN!

Watch boats cruise along the harbor from your waterfront balcony overlooking Broadway Pier, Sagamore Pendry, and Historic Thames Street! Our unbeatable location in the heart of Fell's Point is nearby all of the areas top attractions! Step out the front door to be immersed in cobblestone charm with dozens of restaurants, bars, shops, and boutiques, within steps. Award-winning architecture, local art, and special touches have delighted our guests for years: we hope your group is next!

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

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. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Train Tracks Getaway (Whole house)

All aboard for comfort and charm at Train Track Getaway! This cozy Odenton home is perfect for families and friends, with easy MARC train access to D.C. and Baltimore. Enjoy pancakes on the back porch and marshmallows by the firepit—yes, we’ve got the s’mores kit ready! Inside offers comfy beds, a full kitchen, and space to relax or play. Whether you're visiting Fort Meade or just unwinding, this is your laid-back home base for fun, family, and firepit vibes.

Charming 4 bedroom home just steps to the water!

Charming 4 bedroom home located in the heart of Fell's Point! Located just steps from Broadway Square and the waterfront, this unique space is surrounded by the best restaurants, bars, nightlife and entertainment in the city. This stylish home is the perfect place to stay for group trips and families looking to take in all that Baltimore has to offer. Please note that we allow a maximum of 8 guests and events and/or parties are strictly prohibited.