Holiday houses in Highland Beach

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.

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Charming 3BR 2BR. Imagine waking up with a cup of hot coffee watching the sunrise. Quiet evenings gathering in the gazebo or sitting by the fire pit watching sunset with stunning views of the Chesapeake Bay Bridge, and Eastern Shore from the backyard. Enjoy your own private pier and beach. Steps to community playground and a bigger beach with a pier for crabbing. Just minutes to nearby shopping and Quiet Waters Park. Close to downtown Annapolis, Naval Academy, restaurants, and the shopping mall.

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.

Wonderful Cottage Nestled On Chesapeake Bay

Stunning home a short walk from Chesapeake Bay - a perfect blend of comfort and coastal charm. Stroll, jog or bike in the scenic neighborhood. Hear birds, see deer or watch sailboats glide by. Open-concept design and natural light make our home ideal for entertaining, working from home, or relaxing on the spacious deck. Minutes from local eateries and attractions in downtown Annapolis. One dog max 25 lbs allowed; must be fully potty-trained, included on reservation with applicable pet fees.

Cozy Cottage w/ Beach Access Near Annapolis

Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and easy parking. This 2-bedroom, 2-bathroom home has been thoughtfully decorated with comfortable and cozy amenities. Primary suite features a queen bed, TV, full bath with stand-up shower and beautiful views from large windows. Second bedroom features two twin beds and a TV. Bathroom has a tub-shower combo. Plentiful light and everything you need for a wonderful trip!

Anchors Away

Eastport: Spacious studio boasts high ceilings & lots of natural light with his and hers walk-in closets. Fully remodeled with fresh paint, new floors, bath & kitchen. Tempur-pedic Murphy bed & cozy electric fireplace below a 58” 4K television. Basement houses additional storage & full-size W/D. Grill area. Free off-on street parking. Walking distance to Eastport's finest restaurants, or take the water taxi across Spa Creek into down-town Annapolis or the Naval Academy.

Waterfront-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.

Annapolis Cottage

Conveniently located just minutes from historic downtown Annapolis. Whether you're planning a romantic retreat, a family vacation, or a weekend with friends, this idyllic cottage is the perfect place to make lasting memories. The highlight of this property is the stunning outdoor space that makes you feel like you're staying in a treehouse. Step out onto the deck to enjoy your morning coffee or take a short walk to the neighborhood park.

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Peaceful Escape: Bay Ridge Cottage by the Bay

Come escape to our place at the Bay! Relax and reconnect with loved ones in this classic, family friendly cottage located in the private community of Bay Ridge. The neighborhood is great for walking, biking and relaxing on the private beach right at the end of the street. We love it here because we physically feel ourselves relax within minutes of arriving.