Family-friendly vacation rentals in Annapolis

Astoundingly Charming Bungalow, Bells & Whistles!

This unique property offers its guests the best of both worlds: a single-family house with a large, fenced dog-friendly backyard and a multi-car driveway, within walking distance of the Silver Spring and Takoma Park Metro Stations as well as all the shops, restaurants, bars, and theaters of downtown Silver Spring, MD. Hop on the Metro to play in DC and come back to a comfortable home with a full kitchen, off-street parking, outdoor space, and neighbors who are the friendliest of people.

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Celebrate Summer by Your Private Pool

Lovely 2 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 water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Fed Hill & Inner Harbor / BEST Location & Reviews!

Walk to EVERYTHING! Steps to the Inner Harbor, museums, restaurants, stadiums, & parks. Charm City Circulator & Water Taxi nearby for access to the entire city! Bright home in Historic Federal Hill. Live like a local in an upscale setting! Quiet, comfortable 2 bedroom home perfect for families Preference for booking age to be 25 or older. Baltimore is thriving & evolving, see for yourself how beautiful the area is year round!

Bright 2br w amazing loc and view

850 sq ft 2 bedroom 1 bathroom condo in great downtown Bethesda location. Corner unit with windows everywhere making for great light, energy, and views. Balcony overlooking one of the main Bethesda squares. Close to metro and walkable to more restaurants and bars than you can possibly try. Tandem parking for two cars. New flooring as of June 2023. This condo will exceed your expectations.

Cozy chic apartment in lovely Mt. Pleasant

Cozy, well appointed apartment on tree-lined street in historic neighborhood, close to everything. Private entrance off street, shaded patio in back, sharing tranquil backyard w/host family residence above. This unoccupied apartment is delightful alternative to hotel, w/all amenities. Easy walks to Zoo, Rock Creek Park, and Metro.

Cozy Naptown Perch

Perfectly Placed Perch in Murray Hill neighborhood. 1 mile to USNA stadium; 1 mile to historic downtown. Walk to local restaurants, in town events. Few blocks to water access. 2 bedroom upstairs suite recently renovated. Common room has sofa, table and chairs, coffee/ tea set up. Patio, fire pit available to guests.

Rockhold Creek Cottage

The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular views! The waterfowl are mesmerizing to watch. Just 1/2 block from Happy Harbor and Fishing Charters! No need to make that drive at 4am, you can stay the night before and after for maximum enjoyment!