Holiday houses in East New Market

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Family · Value · Outdoor spaces

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located steps away from Pitcher Dam Creek, leading to Little Blackwater! Kayaks on site! Bring your fishing rod to catch Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining! *BOOKING PARTY MUST BE 21 yrs+

Value · Location · Barbecue

Private Waterfront Estate | Pool, Dock, Kayaks

Wake up to water views, spend your day by swimming in the saltwater pool, kayaking in the river, or fishing on the dock, and end the evening with sunsets. This private 5-bedroom waterfront retreat is designed for families and groups looking to unwind, reconnect, and enjoy the best of Maryland’s Eastern Shore- equipped with high-speed internet- located 15 min from downtown Cambridge and 10 min from the Hyatt Regency Chesapeake Bay, the home is well positioned for wedding stays, and retreats.

Value · Family · River

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Location · Family · Nearby

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Value · Family · Solo travel

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Location · Getting around · Cleanliness

Waterfront Getaway

Come relax at this charming waterfront retreat. Accessible by car or boat and only minutes from downtown Cambridge & waterfront dining. The back patio is a good place to spot bald eagles, ospreys, herons, ducks and other wildlife. Catch crabs right off the dock with provided crab pot. Bring kayaks to enjoy Whitehall Creek, the Choptank River and nearby Whitehall Beach. End your evening roasting marshmallows by the fire overlooking the water (firewood included).

Location · Family · Backyard

Waterfront & Hot Tub! 4 BR/4 BA - Central Location

Enjoy this large peaceful Waterfront cabin-style home with your whole group! This beautifully updated home is super spacious, has lots of great amenities, and is centrally located for easy access to all that Cambridge has to offer! Huge backyard has an oversized patio with private hot tub, fire pit & beautiful water views! We are located on Hurst Creek off the Choptank River. Hurst Creek is a great calm waterway that can be enjoyed in kayaks or small power boats.

Family · Location · Comfort

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Location · Family · Pets

Cottage on Cabin Creek

The cottage is the perfect getaway for couples. It is located on the water with two private piers for you to use. You may enjoy fishing, crabbing, kayaking, canoeing or bird watching from the piers. There is a charcoal grill available and a fire pit. The cottage is secluded enough for relaxation, but not far from local attractions and restaurants. Note the cottage is best suited for 1 to 2 people.

Family · Location · Beach

High St. Art Gallery Suite

This boutique suite is adjoined to the future home of High St. Art Gallery. This historic home was built in 1796 and is being lovingly restored by three generations of a family committed to creating beautiful, unique and comfortable spaces that can be a retreat away from home. This suite has all the details and delights that will make your stay enjoyable and we hope you will come again and again.

Value · Family · Checkout

Beautiful Waterfront Getaway on the Choptank River

A perfect getaway on our waterfront property. You can enjoy your own private beach . You can enjoy fishing , kayaking , paddle boarding, cornhole, and volleyball. We are only 5 minutes from downtown for local attractions and restaurants

Location · Family · Condition