Family-friendly holiday rentals in Chester

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

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.

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!

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.

Spacious Family Retreat in Tranquil Neighborhood

Our home is one of the largest homes in the neighborhood. It is beautifully decorated for your enjoyment. Our large family room will make you feel like you are at home. House is 2,700 sq ft. The house is a close 2.5 miles from the well-known National Zoo. Also, 0.7 miles to the METRO station that has a direct route to the National Mall - a perfect tourist destination.

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!