Dock Holiday

Experience the Difference: Professionally Managed by iTrip Annapolis

Waterfront Thomas Point Retreat with Private Beach & Dock

Escape to the water at this contemporary waterfront home tucked away in Thomas Point, a hidden gem on the Annapolis Neck near Bay Ridge and Arundel on the Bay. With a private beach, new private dock, spacious living areas and beautiful water access, this home is ideal for a family getaways, Navy events or for a comfortable home while relocating or renovating.

Spend your mornings enjoying coffee by the water, launch a paddleboard or kayak from the beach, or head out by boat directly from your private dock. The new dock can accommodate a boat up to 27 feet with approximately a 4-foot draft, making this an especially appealing home for boating families.

The main living level takes full advantage of the waterfront setting with a fully equipped Chef’s Kitchen, Dining Room with seating for 6-8 and a spacious Family Room with gas fireplace. A Billiards Room overlooks the Family Room and includes a tucked-away workspace.

Sleeping Arrangements - Sleeps 7

Main Level

Double Queen Bedroom

Full Bath with dual access to bedroom and living area

Full-size washer & dryer

Upper Level

Waterfront King Suite with private bath, Office Space and Large walk-in closet

Waterfront Queen Bedroom

Twin Bedroom

Full Hall Bath with shower

Outdoor Living

Private beach & pier

Firepit by the water

Waterfront deck with seating & propane grill

Bring your Boat, Kayak or Paddleboard (one Kayak provided by the owner Life Jackets not provided)

Parking for 2-4 SUVs/cars in the driveway and gravel parking pad

Flat-screen TVs throughout

Luxury linens and complimentary starter toiletries

Dog-friendly ($150 non-refundable pet fee per pet)

Ideal Location

13 minutes to Downtown Annapolis

15 minutes to USNA

Easy access to DC & Baltimore (35 miles)

House Rules

At least one guest must be 25+

No smoking, parties, or events

Quiet, family-oriented community

Check-in: 4 PM | Check-out: 11 AM

Perfect for family gatherings, Navy visits, or peaceful waterfront retreats. Dogs allowed with $150 per pet fee paid prior to checkin.

Life on Thomas Point

Thomas Point offers the peaceful feel of a waterfront retreat while keeping you close to everything Annapolis has to offer. Surrounded by the South River and Chesapeake Bay, this part of Annapolis Neck is made for enjoying life outdoors: boating, fishing, paddle boarding, biking and relaxing along the shoreline.