This charming cottage has a great location, just minutes to St. Michaels or Easton, and offers much in the way of family entertainment--pool, hot tub, private dock and great waterviews! The bright cheery kitchen overlooks the water, and guests love the first floor master for parents or grandparents to enjoy. If you are looking for a great first time spot, try the Orchard!

This little gem on the banks of Soltitude Creek is a perfect family getaway! With a pool, hot tub, and canoe for exploring the creeks and tributaries of the Tred Avon River, the kids will forget all about their iPods shortly! A great deck for grilling and abundant nature watching gives this home much to offer the family in need of quality time together. A short distance into the town of St. Michaels, you can easily take in dinner, shopping, an exhibit or free concert in St. Michaels within a ten minute drive. New bedroom configurations give this home more flexibility than ever!

A taste of paradise on the Chesapeake—the beauty hits you before you enter the front door! This spacious, comfortable, home, includes all amenities for a perfect getaway. Big water views throughout the house and stunning sunsets create a peaceful frame of mind for an ideal holiday. Beautifully appointed for both families and couples looking for fun, privacy and romance. The owners are pleased to provide two bicycles, two single kayaks, a tandem kayak and a canoe for you to explore the lush country lanes and calm waterways. The Bellevue-Oxford ferry is an easy ride from here. Chesapeake Pines has a well stocked library for children and adults, a garden room with pool table, plus plenty of games and puzzles for the whole family to enjoy. A croquet set in the garage, and a basketball hoop behind the shed provide more outdoor recreation. For those who must work, there is a large desk with a majestic water view so you can watch the watermen crabbing in the summer. The open kitchen is lovingly equipped with everything you need to put together feasts while enjoying the company of your family and friends. Tucked away next to the deck, looking out to the long water views, under the star spangled sky, with ducks sounding across the creek, is a new spa to help you unwind after a tough day vacationing.

Comfortably furnished, spruced up and ready for your visit, this cottage is perfectly located for small families or two couples visiting St. Michaels who want to be close to the action. A short bike ride or trip into town, with proximity to the St. Michaels Community Pool and Harbourtown Golf Course, all the amenities of staying in town are close at hand, yet you can enjoy the privacy of a waterfront home, with private dock and screened porch. The new owners have furnished kayaks, bikes and even a few crab pots so you can try your own hand at crabbing, and the Crab Claw is just a mile away for a backup plan if you have no luck! There's even an outdoor firepit (firewood not included) to enjoy a marshmallow and hot dog roast, or just warm up on unexpectedly cool evenings! A perfect getaway spot with lots of great amenities.

A deep water pier with picturesque views make this a truly special spot for a weekend getaway, or mini vacation. Couples love the cozy feeling this cottage gives, with plenty of ambience and charm. There is an outdoor firepit, and picnic table at the water's edge.

The master has a light filled sitting room and the other two bedroms with twin beds make this an ideal home for families or even a girls weekend. Just 15 minutes into the town of St. Michaels, you can take in a fall festival or summer farmers market, and come home to relax in your waterfront cottage.

This fantastic 1920's Waterman's cottage has the charm and waterfront location that is hard to come by these days. Restored to give you some up to date comforts, such as new kitchen, added bedroom and renovated bath, this is a great spot to enjoy hours of bay watching, or slip over to Dogwood Harbor and observe one of the last skipjack fleets in the country. Pick up some fresh seafood and have savor a local meal at home with the best seat in the house! A great cottage for those who still appreciate the simple things.

Hudson Manor is fabulous for large families and groups looking to enjoy fishing, kayaking, boating with wide waterviews of the Choptank. Situated approximately 15 minutes outside of Cambridge this property is a vacation destination in itself. This home offers a billiards room, hot tub, waterfront pool, private dock, outdoor firepit and kayaks for guest use. Thre is even a beach volleyball court! The home is designed to accommodate multiple families with flexible sleeping arrangements. If you are looking to get away from it all and simply leave your car keys in the kitchen drawer and relax with your friends and family, Hudson Manor is the vacation home for you.

Tucked away just as you arrive in the town of Oxford, Pride and Joy is a terrific spot for those looking for a step back in time--when you could walk to corner store for milk and an ice cream, meander up the street for walk or check out the local produce stand, or simply sit on the front porch and admire the scenery. A perfect cottage for those wanting to enjoy nothing more than some peace and quiet and the respite that Oxford is known for.

Located on the outskirts of the town proper of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway. This lovingly restored farmhouse has a brand new gourmet kitchen, 5 bedrooms, cozy den with fireplace and a screened porch with gas fireplace to warm you on those breezy summer or early fall mornings. There is plenty of room for everyone to spread out, play games in the casual dining room or enjoy coffee and plan the day overlooking the formal garden. Enjoy the new gazebo, a perfect backdrop for capturing some treasured family photos!