Chesapeake Properties in Cape Charles
A summer week at A Shore Thing is $1195 plus the security deposit.
"A Shore Thing" is a beautifully renovated bungalow just two short blocks from the wide sandy beach of Cape Charles on the Chesapeake Bay. Enjoy a cozy getaway and the small town charm. Single floor living as you vacation in Cape Charles. Walkable small-town with a public beach, free pier fishing, quaint shops, restaurants and a beautiful park.
Embrace pleasant summer weather along the Chesapeake Bay or cooking out on the gas grill in the backyard. Too hot outside? Retire inside to watch TV or play board games in air conditioned comfort. Both bedrooms have wall mounted flat screen TVs to enjoy in the evening. The flat screen TV in the living room is enabled with ChromeCast. Now with WiFi in season.
A week at Bay Breeze in the summer is $2097 plus the security deposit.
Located in the Marina Village of Bay Creek, Bay Breeze is a short walk to the marina beach, the marina, The Oyster Farm restaurant, and just a short drive or bike ride to the historic town and public beach. Large decks let you bask in the sun and enjoy the breeze that fills the air off the Chesapeake Bay. Guests are allowed access to the Bay Creek community pool, in season.
The large living area with flat screen TV on the second floor and pool table just off the kitchen is perfect for entertaining. The first floor master suite and guest bedroom with full bath allows privacy from the living area of the house. A 2nd guest bedroom and full bath are located on the second floor. There is also a 3rd floor that is equipped with small futons for an additional private sleeping area or just a quiet escape.
Bay Breeze is perfectly outfitted for larger groups or just a private getaway.
Baydream is a light-filled Victorian cottage in the heart of Cape Charles that has been fully gutted and completely renovated! New electric, plumbing, HVAC, roof, windows, and vinyl siding. Enjoy the historic character with modern comforts. Spacious rooms have gleaming hardwood floors, handsome molding and staircase, French doors, and plenty of closet space. Large kitchen with white cabinetry opens out on to a large back deck and plenty of parking on shell lined driveway. Welcoming front porch faces west to enjoy colorful sunsets over Central Park. Perfect location for listening to summer concerts in the park. Second floor has ample master suite with private bath, large foyer, and 2 additional bedrooms. Close to beach, restaurants, shopping, library, 2 PGA golf courses, 2 marinas, boat ramp, and Central Park.
Bayview Cottage only goes by the week in summer for $1925 plus the security deposit.
This house has the view you've been looking for! Just off the Chesapeake Bay in historic Cape Charles with one of the best views of the water and steps to the beach. Sit on the screened in porch and watch the boats sail by.
This Cape Cod has three bedrooms, 1 1/2 baths with an outdoor shower and can sleep up to 6 people. Close to downtown restaurants and shops, and a short drive to two premier golf courses: Jack Nicklaus and Arnold Palmer. Enjoy lots of choices for water recreation or just relax in this charming vintage seaside town.
Beach Tribe is $1981 for a summer week plus the $300 refundable security deposit. ONLY FULL WEEK BOOKINGS WILL BE ACCEPTED FOR 2019.
Discover the 'Perfect Beach Town' according to Southern Living magazine, have fun in the sun and explore the beauty of Virginia's Eastern Shore from a brand new home with many amenities including pine hardwood floors, premium stainless steel appliances, granite countertops and three en suite bathrooms, two with large walk-in showers. Located in a quiet neighborhood, perfect for families, but close to groceries, restaurants, shopping, beaches and marinas. Enjoy Happy Hour on the second story deck and later amazing sunsets and star-gazing. Your vacation rental includes access to a private community pool and tennis court just a short walk away.
Fish, crab or launch your kayaks off the community pier also just a few steps away; stroll the fitness trail; watch the kids play tag or hide and seek in the large backyard. Minutes away from the Cape Charles public beach with plenty of parking or ride your bike. Bring your boat and launch at nearby Cape Charles Town Harbor or Kiptopeke State Park. Plenty of parking including room for your boat.
The newly constructed 1800 sf home has two master suites with king sized beds and a third bedroom with four single beds, a flat screen TV, DVD, and it's own bathroom. The house also includes a 42 inch LCD HD TV with Blu-ray DVD player and an extensive video library. Enjoy family time watching movies or playing one of many provided board games.
Beach Tribe is unique from the tin roof to the wooden crab crafted into the eaves fronting the house. We have tried to combine classic features such as farmhouse heart of pine floors with modern amenities such as a high fidelity entertainment center and high speed internet.
Driveway with parking for three vehicles or boat. Covered front porch and patio off kitchen. Large upstairs deck. Outdoor shower.
Chessie View is steps from the beach!
Chessie View goes by the week in 2019 for $3024. Call our office to book a week in 2020!
Completely renovated beach front cottage will please everyone! Large sun porch with cozy dining & sitting areas. The 1st floor has a living room with large sofa & chairs with a TV/game area. The new kitchen has an eat-in island. The dining room seats 6. The 1st floor bathroom has a shower with a seat and the adjoining laundry area leads to a the back deck for a bit of shade, grilling, or quiet time. The 2nd floor has full hall bathroom, master suite with 3/4 bath, bedroom #2 & bedroom #3 both have queen beds. The wet bar area leads outside to a 2nd floor deck overlooking the bay. The 3rd floor includes bedroom #4 with twin beds, bedroom #5 has a double bed with a twin air mattress available, and a 1/2 bath in the hall. All bedrooms have beautiful views of the bay, TVs, and internet.
Grab a towel & cross the street to the bay! Ideal for families.
Classically Current rents by the week in summer for $3949 plus the $300 security deposit. Reservation requests other than full weeks in summer or for off-schedule arrivals are not allowed through online booking. PLEASE CALL IF YOU ARE INTERESTED IN A SHORTER STAY. Enjoy the home with a 2 night minimum outside the summer season.
Third on Coastal Livings America's 10 Happiest Seaside Towns list for 2018. Great place for families or couples. Come enjoy the public beach, fishing pier, kayak tours, biking around town, or golf either a Nicklaus or Palmer course. Do a wine tasting at Chatham Vineyards, sample local beer at the Cape Charles Brewing Company, or sample spirits at the Cape Charles Distillery. You can enjoy lots of outdoor activity or just a lazy day around town.
The town continues to grow adding new shops and restaurants. Beautiful marinas and local watermen bring in fresh seafood at the Harbor.
The beautiful Victorian home is an easy walk to the beach and just 2 blocks from the main street Mason Avenue to experience shopping and restaurants.
The home has new furnishings and artwork throughout to create a calming environment for guests. Enjoy the entire home of just under 4000 square feet. Plenty of space and privacy to create happy memories. It has a wide staircase, pocket doors, 10 foot ceilings, original light fixtures, ceiling fans, and transom windows.
Amenities include- Smart TVs to stream your favorite show, 2G & 5G Wifi, three zone air conditioning, and on demand hot water.
Expansive front porch to enjoy with friends and family. Or sit on the screened in back porch overlooking the park watching the children play or enjoying local concerts and events.
Private parking off the alley behind the home for 2 cars.
Nicely appointed kitchen with high end appliances including two ovens.
New Weber propane grill on the screened in porch.
Large dining table for large gatherings post a day at the beach.
Family room with plenty of seating and a TV.
Parlor can be closed off to use as another sleeping location or to quietly read a book.
Half bath under the stairs for guests.
Beautifully appointed master bedroom with king bed, walk in closet, and private bath with shower and soaking tub. Queen bedroom with large windows overlooking the quiet street.
Twin bunk room for the children.
Queen bedroom with balcony. Sit in the rocking chair overlooking the park off this bedroom.
Bathroom with shower.
Laundry room with full size washer and dryer.
Large area for games and wet bar with view of the Bay.
Full bathroom and two additional bedrooms. The bedrooms have a full and a twin.
Includes propane grill, plenty of outdoor seating, screened in porch with ceiling fan, beach chairs, a beach umbrella, 2 bikes, and small sand toys.
The rental of the home includes linens, towels, beach towels, and Internet/WiFi. No smoking or pets.
A summer week at Coastal Charmer is $2080 plus the security deposit. ONLY FULL WEEK BOOKINGS WILL BE ACCEPTED FOR 2020 BY PHONE.
Come fall in love with all Cape Charles has to offer. Relax in this coastal living family home a short walk to Cape Charles beach or the shops on Mason Avenue. Enjoy the wraparound porch with plenty of seating.
Walk in the front door and watch TV in the family room with plenty of comfortable seating. Or walk thru the brand new kitchen and grab a snack to eat at the eat in area or more formal dining area with shiplap wall. Behind the kitchen is a large laundry room with a full washer and dryer, and a full bathroom. Continue to the backyard for outdoor seating near the grill. Coming back from the beach? Rinse off in the outdoor shower out back before going back in to relax. Beautiful hardwood floors throughout.
Upstairs there are 4 bedrooms and another full bathroom. Bedroom one has 2 sets of bunk beds and sleeps 4. Bedrooms two and three have a Queen bed in each and bedroom four has 2 twin beds.
Driftwood Beach has only one available week left for July for $3466 plus the security deposit. Book by the week in prime season and 4-night minimum in the off-season. Shorter reservation requests will not be accepted.
Enjoy your vacation with private beach front on Virginia's Eastern Shore. This cherished getaway is close to the Chesapeake Bay Bridge Tunnel that takes you to (or from) the Virginia Beach/Norfolk area including Norfolk International Airport - an easy 40-minute drive.
It is a short drive to the historic town of Cape Charles where you can appreciate the Southern hospitality. Explore the quaint shops, feast on local seafood and farm produce, and plan your adventures. Or enjoy your retreat and sip wine in privacy enjoying the beautiful bay sunsets.
Escape but stay connected with Free WiFi. Enjoy the beauty of the Chesapeake Bay and the modern comforts of Driftwood Beach.
A week at Flip Flop Inn during the summer will be $1126 plus the security deposit.
Remodeled in 2018, including a new AC system. Check out the new photos.
Cozy 2 bedroom 1 bath that can sleep 5 with a queen, twin trundle, and a provided twin air mattress.
Enjoy a cozy getaway and the small town charm. Single floor living as you vacation in Cape Charles. Walkable small-town with a public beach, free pier fishing, quaint shops, and restaurants.
Embrace pleasant summer weather along the Chesapeake Bay relaxing on the front porch or cooking out on the gas grill on the back deck. Too hot outside? Retire inside to watch the flat screen tv or play board games in the central AC.
Oyster Shell goes by the week in summer for $2028 plus the security deposit. There is 3-night minimum for summer stays. ONLY FULL WEEK BOOKINGS WILL BE ACCEPTED FOR 2020 BY PHONE.
1894 renovated Cape Charles Victorian Beach House with generous room sizes and open floor plan. Home faces south and has lovely breezes on the front porch facing tree lined street. Lots of windows bring in plenty of light. Walking distance from beach on the Chesapeake Bay and shops in town. Back yard has gas grill and newly built pebble patio with circular table and chairs and umbrella for outside dining. Separate play room for kids or to play cards and games. Lots of comfortable seating in family room and living room. Roomy dining room with large dining table and chairs. Great for family dining or entertaining.
Newly built convenient golf cart parking and charging station off the alley for two standard golf carts.
Enjoy a week in Pelican Place for $1753 plus $300 REFUNDABLE security deposit
Fully Restored 1886 Beach Cottage Close To Downtown Shops
Pelican Place, once featured on THIS OLD HOUSE, has all the comfort of today with the charm of yesteryear. Once a railroad office, the cottage was moved to the present site; the interior was gutted, deconstructed with structures salvaged and renovated, and then rebuilt with modern plumbing and wiring, central air and heat, and other modern comforts yet still retaining its period character. The cottage is fully equipped for a care-free vacation: a huge, well stocked kitchen, comfortable living room with a 50 inch TV and entertainment center, games, movies, and Netflix. Sleep well in the comfortable beds. For your beach needs, there are an outside shower, beach chairs and toys, and even off street parking large enough for a boat.
A summer week at The Playhouse is $1351 plus the security deposit.
Enjoy this renovated Cape Charles single family home. This spunky little house has modern updates while reminding you of the history of Cape Charles. Accommodations include 3 bedrooms, 2 full baths, on demand hot water, full sized washer and dryer, dishwasher, central heat and air, and a screened front porch. 540 Jefferson is just a short walk to the local beach, marina, and downtown Cape Charles.
Cape Charles offers a family friendly beach, fishing pier, quaint shops, day spa, and local pub, as well as access to a first class golf course. Impossible not to relax and have a great time here!
Ray of Sunshine goes by the week in summer for $1954 plus the security deposit.
New construction, new furniture, new appliances, newly decorated.
The nicest backyard in town for entertaining...includes a large patio, built in fire pit, outdoor seating, and hammock.
The entire 3rd floor functions as a large bedroom with its own heating and AC.
Private driveway so you don't have to compete for off street parking.
Nice size front porch with rockers.
Big flat screen TV with HBO, Cinemax, Showtime. All the movie channels for summer.
Pleasant walk to the beach or the Oyster Farm Restaurant and Marina.
A summer week at Robyn's Nest is $2011 plus the security deposit. Please let us know if you would like to book a shorter stay! Robyn's Nest will accept 2-night bookings.
Find yourself relaxed at the Robyn’s Nest, a 1920 historical home located within the Historic Cape Charles of the Eastern Shore of Virginia. You will enjoy sipping a cold tea on one of the porches or on the beaches of the Chesapeake Bay merely three blocks from the door step.
Robyn’s Nest captures the local charm of Cape Charles while also featuring art and textiles from throughout the world. The spacious – more than 2,000 square feet - accommodations include four bedrooms located upstairs and two full baths. The large front bedroom includes an antique posted full size bed, twin day bed, and two hide-a-beds. The middle room includes a queen bed and a twin bed. Each of the other two back bedrooms (one bedroom is accessed through the other) includes a queen size bed. The downstairs features a front reading room, a middle entertainment room for lounging, a formal dining room, and a recently renovated kitchen. Amenities and supplies in the house include various games, tennis rackets, beach supplies (chairs and towels), WiFi flat screen television, Weber propane grill, and a lovely picnic table for back yard barbecues.
Southern Living voted Cape Charles as the “The Comeback Town” within the top five “Perfect Little Beach Towns.”
Salt Therapy is a short walk to Cape Charles Beach, Central Park, and one block from the shops on Mason.
Conveniently located, comfortable, and nicely furnished. Modern new appliances and comforts inside with an open layout, great for entertaining and families. Small town charm outside and inviting landscaping. Enclosed back yard and three separate covered porch areas to relax and unwind.
Unusual configuration upstairs. A couple steps up to the left is the first bedroom with a queen and the twin. Steps up to the right access the rest of the second floor. The first door is to the nested bedrooms. The 3rd bedroom is accessed through the 2nd. The back bedroom has the foosball table. A short hall leads to the full bath upstairs.
Please note this is a historic home and has a steep staircase leading to the second level and may be suitable for every guest.
Off-street parking to the left of the house for cars or golf carts.
Sand Castle goes by the week in summer for $1925 plus the security deposit.
3 bedrooms, 2 full bathrooms (handheld showers), sleeps 6
Sand Castle is a quaint, little cottage located in the heart of historic Cape Charles, on Virginia's Eastern Shore. It is ideally situated just a few steps from the center of a half-mile long public beach, along the Chesapeake Bay. It is within easy walking distance of every attraction in the town of Cape Charles. The waters of the Bay, as well as the most spectacular sunsets to be seen on the East Coast, can be viewed from the spacious living room, and from the large open porch spanning the front of the cottage.
Sand Castle comfortably sleeps six, and is available for weekly rental throughout the year.
Serendipity has full week openings in September for $1822 plus the security deposit.
Come visit Cape Charles - 1 king, 1 queen, and 4 twin beds (one bunk bed).
4 blocks to the beach! 2-story beach house with screened porch (circa 1888) is fully remodeled. Original oak floors downstairs. Spacious living room with handsome brick fireplace flows into dining room through large French doors. Eat-in kitchen bar. Original wainscot in kitchen and adjacent utility room. Smartly updated 1/2 bath and additional back mudroom add to the functionality of the space. Upstairs there are refinished pine floors and 3 light filled bedrooms along with a beautifully remodeled full bath. Curb cut and driveway with off street parking. Partially fenced backyard.
ONLY FULL WEEK BOOKINGS WILL BE ACCEPTED FOR 2019. The Nor'wester goes by the week in summer for $1914. Early Bird Pricing $1627 inclusive/week for May-June 8 bookings.
SOUTHERN BREEZES, NOR'WESTER - The first word guests guests utter is "Wow!" How loud the "Wow" expresses how charming, spacious, and clean the house is. Cape Charles is a Victorian village, and this grand old four-level brick duplex epitomizes the character of the town. Built in 1923 for two families, that's the way SOUTHERN BREEZES remains today. Family lives on the 3rd floor and the left side. Guests of NOR'WESTER have access to their own first, second, and basement floors. The NOR'WESTER sleeps up to 8 (maximum 6 adults). The NOR'WESTER includes a front porch, living room, dining room, eat-in kitchen and half bath on the first floor. An easy walk up the presentation staircase brings you to three bedrooms and a full bath. The full basement includes a laundry room with stall shower and sink on each side with four bicycles and crabbing gear, just a few steps down from the outside entrances.
The NOR'WESTER has 1 king bed, 1 queen bed, two twins (that can become a king), and bunk beds downstairs for kids. The bunks are on the sleeping porch sun room for kids old enough to stay downstairs by themselves. The bedrooms also have ceiling fans and transoms over the doors. Bed selection ranges from firm to plush, with memory foam toppers and lots of pillows. SOUTHERN BREEZES offers premium quality blankets, pillows, and towels (including beach towels).
Enjoy Cracker Barrel rockers and wicker furniture on the divided front porch. Each room has a window AC (6 total) so everybody can be happy at their own preferred temperature. Or, open the big windows and catch the breezes! Cable TV/DVD plus online movies and music from Netflix, Pandora, Amazon, Hulu, and more. Of course, we have high-speed WiFi Internet! We also have lots of books and magazines - plus the town library is a 5-minute walk away! The living has both a sofa and a love seat - ideal for watching movies on the flat panel TV. The formal dining room seats 8 and the kitchen seats 6. The Kitchen includes a double-door fridge with water and ice dispenser, dishwasher, disposal, microwave, coffee maker, toaster, blender, electric teapot, stainless steel pots and pans, dishes, silverware, TV, etc. There's a shower/bath on the second floor, another shower in the lower level laundry room, and a private hot shower outside (our favorite). The laundry room has full-size washer and dryer. We also provide the various soaps.
There are both gas and charcoal grills in each separate picnic area out back. NOR'WESTER has cruiser bicycles and shares more with Nor'Easter in the carport.
Arranging to stay at SOUTHERN BREEZES is easy. You'll receive a welcome letter with everything you need to know, including the lock box combination on the front door. When you leave, just return the key to the lock box - that's it. This house has it all: historic charm, perfect location to beach and town, and reasonable rates - all geared toward families looking for a relaxing, spacious, clean but not too fancy old homestead for gathering up to 6 adults plus two children and the family dog. Parents, this are is perfect for children! There's a huge park and playground just up the street. Bikes are the way to go! Cape Charles is also golf cart legal. If you rent a cart, you can keep it in the carport out back. There's a skateboard park, tennis court, basketball court (at Cape Charles Baptist Church), beach volleyball games every night in summer, fishing and crabbing. For a change of pace, take a day trip across the bridge to Virginia Beach, Busch Gardens, and Wiliamsburg. Or simply explore all that Eastern Shore has to offer.