Family-friendly holiday rentals in Chester

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

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!

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Lofty Dreams, 2016 Brookstone RV - Waterfront

41' 2016 Brookstone Fifth Wheel RV located at Jones Creek Marina in Sparrows Point, MD. Convenient, Waterfront Environment near Tradepoint Atlantic, downtown Baltimore, close to I-695, I-95, in a fairly quiet/peaceful environment. The RV is located in a working boat yard. This is not a resort or vacation destination. If you enjoy sitting by the firepit at the waterfront in a quiet cove - you will enjoy this property.

"Wittman Cottage"

Wittman Cottage is located on a beautiful stretch of waterfront views. It is a very nice vacation spot for the family. You can relax and watch the beautiful sunsets from our very large screened porch, or drive to shop and dine in St. Michael's and visit the Maritime Museum which is only 7 miles away..

Chester Riverfront At Kent Narrows

Our place is spacious, has great water views, a private beach and is close to restaurants and dining. You’ll love it because of the bay, hot tub, pool, and outdoor space. Our place is good for couples, friends, solo adventurers, and families with kids.

Pet Friendly Garden Apartment Near Annapolis

Cozy garden apartment w/private entrance, queen bed and twin day bed with trundel, bath and sitting room, and includes a refrigerator, microwave and coffee maker (there is no kitchen). Convenient to historic downtown Annapolis, Baltimore & Wash DC.