By continuing to navigate on this website, you agree to our use of cookies and tracking for statistical and personalisation purposes in order to enhance your experience on this website. You can also click the 'Accept' button, in order to agree and close this banner - the banner will not be displayed for you in the next month.

View All Chesapeake Vacation Properties

Find Properties By
Clear filters
Cape Charles
"A Shore Thing" is a beautifully renovated bungalow is just two short blocks from wide sandy beaches 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 the flat screen TV in the living room or play board games in air conditioned comfort. Both bedrooms have wall mounted flat screen TVs to enjoy in the evening.
A Shore Thing
2 Bedrooms, 1 Baths, 576 Sq. Ft., Sleeps 4
fishing, Golf Course, Washing Machine
Cape Charles
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. The large living area with flat screen TV on the second floor and pool table just off the kitchen is perfect for entertaining.
Bay Breeze
3 Bedrooms, 3 Baths, Sleeps 8
Central Air, Golf Course, Washer & Dryer
Cape Charles
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

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.

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 summer for $3001 plus the $300 refundable security deposit.  ONLY FULL WEEK BOOKINGS WILL BE ACCEPTED FOR 2019.

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 full bathroom and 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 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 trundle, and a 1/2 bath in the hall. All bedrooms have beautiful views of the bay, TVs, and internet.

Chessie View
5 Bedrooms, 3.5 Baths, Sleeps 11
Golf Course, Internet, Washer & Dryer

Come enjoy the hospitality and charm of Cape Charles with family and friends. Fully renovated 1910 Victorian home. Enter a tranquil oasis and be transported back in time with the wide staircase, pocket doors, 10 foot ceilings, original light fixtures, and transom windows. 

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. 

 Modern amenities include- Smart TVs to stream your favorite show, 2G & 5G Wifi, three zone air conditioning so each floor is the perfect temperature, and on demand hot water for showers post your return from the beach. 

 Spend lazy summer days on the expansive front porch with friends and family. Or sit on the screened in back porch overlooking the park watching the children play or enjoying local concerts throughout the summer.  

 Easy walk to the beach to enjoy the calm waters of the Chesapeake Bay. Just 2 blocks from the main street Mason Avenue to experience shopping and restaurants. 

 Private parking off the alley behind the home for 3 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, and beach towels. 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
Walk in the front door and watch TV in the family room. Or walk thru to kitchen and grab a snack at the eat in area or more formal seating. Behind the kitchen is a mudroom 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. 

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 is available by the week in summer for $3430 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.
Driftwood Beach
6 Bedrooms, 5.5 Baths, Sleeps 15
Air Conditioning, fishing, Golf Course, Internet, Washing Machine
Cape Charles

Please send an inquiry before trying to book for 2019 from 6/22 onward. Next year's availability calendar has not been updated.

A week at Flip Flop Inn during the summer will be $956 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
Cape Charles
Fully equipped home with king bed in master bedroom, full bed in second bedroom, full and twin beds in third bedroom, and full futon in upstairs TV room. Madison House has a renovated kitchen with Corian countertops and stainless steel appliances. There is a gas stove, dishwasher, microwave, and is fully stocked with cookware and dishes for those who want to cook. There is an upstairs sitting room off the TV room that also has a full refrigerator and sink for those summer evenings where you want to relax and read a book or enjoy a drink. You can find beach chairs and a gas grill in the backyard shed. 

Cape Charles, Virginia is the Eastern Shore's best kept secret! It is a mile square historic, quaint town tucked between 2 championship golf courses designed by Jack Nicklaus and Arnold Palmer. This historic town has a quiet, pristine public beach that has warm shallow water ideal for children and boasts gorgeous sunsets. There is a harbor and a marinas on either side of town and excellent restaurants nearby, along with quaint shops and boutiques. The shops and beach are two short blocks from Madison House.
Madison House
4 Bedrooms, 2 Baths, Sleeps 13
Golf Course, Washer & Dryer



Facebook Twitter Pinterest YouTube Google Plus Instagram