Family-friendly holiday rentals in Cambridge

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

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.

Spacious Home in Private Neighborhood with Beach

A beautiful and spacious home located on the Severn River in the gated community of Epping Forest! The house is just 7 miles from downtown Annapolis and offers guests a private, secluded home away from home. A private beach and club house are located within walking distance! Enjoy a fire on either of the two levels of private decks, or gather around the large dining room table for any of the provided board games. An abundance of amenities will make your stay more than comfortable!

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

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.