Holiday houses in Cape St. Claire

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.

Location · Family · Long stay

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Value · Family · Amenities

Annapolis waterfront, private pier with kayaks

USNA-grad owned. Lovely waterfront home on half acre 5.5 miles to downtown historic Annapolis with private pier for waterside fun. Designed around entertaining with spacious, well-equipped kitchen, separate dining area, plenty of room for everyone to dine indoors or out. The main floor beams with natural light. Perfect for families and small groups to gather for local college events, sporting matches, boat shows, wedding +. Easy day trip access to Baltimore, Washington, DC and the Eastern Shore.

Family · Location · Sleep quality

Celebrate Summer In Your Private Pool & Hot Tub

Lovely two acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing waterfront home is conveniently located eight miles from the Naval Academy and downtown Annapolis. WE DO NOT HOST PARTIES OR EVENTS, AND UNREGISTERED GUESTS ARE NOT PERMITTED ON THE PROPERTY AT ANY TIME.

Value · Family · Long stay

Firepit + Basement Lounge + Putt Green | Sleeps 12

Welcome to your 5 ⭐️ Escape! Spacious 4BR home for upscale getaways, families, and Naval Academy visits. Sleeps 12 and is under 5 minutes from the Beach and 10 minutes from downtown. Enjoy a huge backyard with firepit, cornhole, and putting green, plus a basement bar for evenings in. Fully stocked kitchen with all cookware, dishes, appliances, and a coffee bar with complimentary coffee and tea. Free parking, fast Wi-Fi, dedicated work desk, and pets welcome. Book early—prime dates fill fast.

Location · Value · Backyard

Pet-Friendly Annapolis Getaway | USNA & Beach/Bay

Unwind in this inviting 3-bedroom Annapolis getaway, just minutes from the U.S. Naval Academy, Sandy Point Beach, Chesapeake Bay, and Downtown Annapolis. Set in a peaceful neighborhood, this pet-friendly home is perfect for families, Navy parents, couples, and groups. Enjoy a bright, comfortable living space, fully equipped kitchen, and private deck with peaceful wooded views. With easy access to USNA events, beaches, waterfront dining, and local attractions, everything you need is close by.

Location · Value · Hospitality

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.

Value · Family · TV

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Location · Value · Parking

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!

Location · Value · Sleep quality

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

Location · Family · Condition

Family Escape | Beach + Water + Shops Nearby

Welcome to The Cape Escape ⚓️ — a family & pet-friendly Annapolis getaway in waterfront Cape St. Claire! Enjoy 4 bedrooms, 2.5 baths, 2 king beds, 2 twins + bunk room, two living spaces, game room & fenced yard. Walk to water, beach, marina, playground & tennis courts. Neighborhood shopping includes Grauls, Rita’s, Dunkin’, Blue Rooster Café, Ace Hardware & more. Perfect for Navy families, USNA visits, Commissioning Week & Chesapeake Bay getaways!

Location · Family · View

Captains Quarters Oasis Near Annapolis, Sleeps 4

This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

Family · Value · Amenities