
Holiday rentals in East New Market
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Top-rated holiday rentals in East New Market
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4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre
Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway
ValueFamilySleep quality
4.97 out of 5 average rating, 103 reviews
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.
LocationValueIndoor spaces
4.92 out of 5 average rating, 129 reviews
Private Waterfront Cottage with Pool and Poolhouse
Totally Private, quiet, deep water-front cottage with wood-burning fireplace and exclusively private 60' Lap Pool (open mid-April to mid-October), large open Pool House and Pier. The nearest residences in the area are far removed from this cottage for a great feeling of seclusion and privacy at cottage, pool, lawns, and gardens; all for the exclusive use of cottage guests. Located between the beautiful villages of Easton and Cambridge -- close to Trappe, Oxford, and St. Michaels. STRN-26-13
LocationFamilyIndoor spaces
4.85 out of 5 average rating, 47 reviews
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.
FamilyLocationComfort
4.92 out of 5 average rating, 39 reviews
Warwick Farms waterfront Retreat
Bright, rustic, waterfront farmhouse retreat resting on over 9 acres. The water views can be enjoyed almost anywhere from this 5-bedroom, 3-bathroom home. Drift off to sleep in the Master suite overlooking the water. Enjoy rocking on the porch, relaxing by the large private pool, or mastering your skills at the endless opportunities on the water. A private pier for your crabbing, fishing, and boating pleasures awaits you. Catch dinner! There is a public boat ramp less than a mile away!
LocationFamilyLaundry
4.93 out of 5 average rating, 14 reviews
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.
FamilyValueAccuracy
4.99 out of 5 average rating, 658 reviews
Cozy Tiny House at Snug Harbor Marina
Escape to this cottage located at Snug Harbor Boat Ramp. Perfect for boaters, couples, and anyone looking for a peaceful waterfront getaway, this cozy retreat offers easy access to the water. The space features an open-concept living area, a kitchenette, and bedroom. Outside, relax on the porch with your morning coffee while enjoying the surroundings. The boat ramp is just steps away, making it easy to launch your boat, spend the day fishing, or explore the beautiful waterways nearby.
LocationWifiCheck-in
4.82 out of 5 average rating, 11 reviews
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.
ValueFamilyRiver
4.99 out of 5 average rating, 228 reviews
Magical Waterfront Home Dock, Firepit, Family Fun!
Heron's Rest is a stunning home w/ arguably the best water views in Cambridge from nearly every room, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and charming historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. Rare location w sunset and sunrise views!
LocationValueComfort
5.0 out of 5 average rating, 55 reviews
Waterfront Getaway with Dock
Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!
FamilyValueBack garden
4.93 out of 5 average rating, 196 reviews
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.
LocationFamilyKitchen
4.94 out of 5 average rating, 49 reviews
Stunning Chesapeake waterfront home
Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.
FamilyLocationSleep quality
4.99 out of 5 average rating, 98 reviewsPopular amenities for East New Market holiday rentals
Other great holiday rentals in East New Market

Charming cottage, FP, 1 blk water, historic area
FamilyLocationRiver
5.0 out of 5 average rating, 49 reviews
Eastern Shore Retreat!
ValueLocationCondition
5.0 out of 5 average rating, 58 reviews
Modern Chesapeake Waterfront - Heated Pool - Dock
LocationFamilySleep quality
5.0 out of 5 average rating, 14 reviews
Relaxing Retreat on the Hudson
ValueFamilyCondition
4.96 out of 5 average rating, 81 reviews
The Cottage at Broad Creek
LocationWalkabilityComfort
5.0 out of 5 average rating, 54 reviews
Historic Home in the Heart of Cambridge
FamilyLocationCleanliness
4.93 out of 5 average rating, 74 reviews
RELAX, You're on RIVER & POOL time!
ValueLocationView
5.0 out of 5 average rating, 65 reviews
Waterfront Getaway
FamilyLocationHospitality
5.0 out of 5 average rating, 17 reviewsDestinations to explore
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- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Bethany Beach Boardwalk
- Assateague State Park
- Cape Henlopen State Park
- Dover Motor Speedway
- Northside Park
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Breezy Point Beach & Campground
- Roland E Powell Convention Center
- United States Naval Academy
- Ocean City Boardwalk
- Annapolis City Dock
- Funland
- Downtown Annapolis Partnership
- Bear Trap Dunes
- Gerry Boyle Park
- Navy–Marine Corps Memorial Stadium
- Quiet Waters Park
- Dewey Beach Access
- Calvert Marine Museum





