By continuing to navigate on this website, you agree to our use of cookies and tracking for statistical and personalization purposes in order to enhance your experience on this website.

View All Chesapeake Vacation Properties

Find Properties By
Clear filters
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 Shore Thing
2 Bedrooms, 1 Baths, 576 Sq. Ft., Sleeps 4
fishing, Golf Course, Washing Machine
Cape Charles

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.

Bay Breeze
3 Bedrooms, 3 Baths, Sleeps 8
Central Air, Golf Course, Washer & Dryer
Cape Charles
Baydream goes by the week in summer. 

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.
3 Bedrooms, 2.5 Baths, 1,824 Sq. Ft., Sleeps 6
Golf Course, Washer & Dryer
Cape Charles

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.

Bayview Cottage
3 Bedrooms, 1.5 Baths, 1,600 Sq. Ft., Sleeps 7
Air Conditioning, Golf Course, Washing Machine
Cape Charles

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.

Beach Tribe
3 Bedrooms, 3 Baths, 1,800 Sq. Ft., Sleeps 8
fishing, Internet
Cape Charles

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.

Chessie View
5 Bedrooms, 3.5 Baths, 2,300 Sq. Ft., Sleeps 11
Golf Course, Internet, Washer & Dryer

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.

1st floor

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.

2nd floor

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.

3rd floor

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.

Classically Current
6 Bedrooms, 3.5 Baths, 4,000 Sq. Ft., Sleeps 13
Air Conditioning, Golf Course, Internet, Washing Machine
Cape Charles

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.

214 Tazewell
4 Bedrooms, 2 Baths, 1,600 Sq. Ft., Sleeps 10
Central Air, Golf Course, Washer & Dryer
Cape Charles

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.

Driftwood Beach
6 Bedrooms, 5.5 Baths, Sleeps 15
Air Conditioning, fishing, Golf Course, Internet, Washing Machine
Cape Charles

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.

Flip Flop Inn
2 Bedrooms, 1 Baths, Sleeps 5
Golf Course, Washing Machine



Facebook Twitter Pinterest YouTube Google Plus Instagram