Sail Cape Charles

  • Enjoy a sunset cruise in the bow of the 29' sloop StewardShip in the Cape Charles Bay.

    Enjoy a sunset cruise in the bow of the 29′ sloop StewardShip in the Cape Charles Bay.

Nearby Rentals

–  Sail Cape Charles

Enjoy a sunset cruise in the bow of the 29

Sail Cape Charles

Two Hour Sail $50 per person Three Hour Sail $65 per person We will be happy to entertain your special cruising needs!S/V Stewardship carries a maximum of four passengers.
1 – Pink Pearl – 1 Miles

Pink Pearl

Pink Pearl

2Wonderful accommodations at an affordable price. Just 6 1/2 blocks to the beach, this comfortable cottage is located in the Historic town of Cape Charles. Offering 3 bedrooms and 2 full baths, this home can sleep 6 comfortably. A fully equipped kitchen and laundry room add to the convenience of your stay. Walking or biking distance to the beautiful town beach, marina, shopping and restaurants. Rent a golf cart to get around town. Cape Charles is Golf cart friendly.  Back alley access for your boat or RV.
We offer concierge services and will be glad to assist you with dining reservations, golf cart, kayak and bike rentals as well as bookings for fishing and sailing charters and guided kayak tours. Feel free to call us about any of your needs.                                                        


Beautiful Chesapeake Bayfront Home with private beach. Offering Community Pool, Tennis, and Lake Allure, a freshwater lake.


Beautiful beachfront home on 2+ acres with 185’ private beach on the Eastern Shore of VA, with water swimmable even at low tide. Private community with pool, tennis court, volleyball net and private lake. Short drive to world class golfing at Bay Creek, with both Palmer and Nicklaus Signature golf courses. Dolphins, pelicans, ospreys, and eagles often seen right from the beach. Take long beach walks, go beach combing, kayaking, crabbing, fishing, and birding. All of this can be done right from the beach and/or at many fabulous locations nearby. Kayak rentals and eco tours nearby. Near Kiptopeke State Park, offering nature programs and Eastern Shore Wildlife Refuge with nature trails and  information center. Quaint town of Cape Charles nearby with town harbor, town pier, shopping and restaurants. Short drive to VA Beach Oceanfront. Easy day trip to Busch Gardens, Williamsburg, Jamestown, and Chincoteague. Cap each perfect day watching amazing sunsets from deck or beach.

Enjoy, kayaking, paddle boarding and beach combing. Kayaks can be delivered to the home during your stay.

Special rates for Bay-Creek Golf courses are available with this home.

This gorgeous, sunny home provides beautiful Chesapeake views from almost every room.

Two spacious family rooms on the first floor each have a TV, books, games and comfortable seating, The fully equipped kitchen is perfect for entertaining and relaxing with friends and family. The kitchen is open to the dining room, family rooms and the expansive deck which overlooks the bay. The first floor bedroom offers a queen size bed and adjacent new full size bath with seaglass tiled shower.

The second floor features a magnificent master bedroom with a sitting area where you awaken to mesmerizing views of the bay. There are two additional bedrooms, one with a queen bed and views of the bay and the fourth bedroom with twin bedding. A sleeping loft offers a comfortable queen size sleeper sofa and TV.

The lower level offers a queen bed with a full bath and a spacious entertainment area with a large flat screen TV and an air hockey table.





3 – BAYHOUSE-Elevated Beach with steps down to the water – 15 Miles

BAYHOUSE-Elevated Beach with steps down to the water

CHESAPEAKE BAY FRONT HOME. Enjoy this beautifully appointed 4 bedroom, 3.5 bath waterfront vacation home on almost 2 acres of prime real estate with the most fantastic sunsets over the Bay. Secluded location, yet 10 minutes to shops and restaurants. There are plenty of windows in the home to take advantage of the views out to the Bay. Offering a first floor master bedroom with master bath and jacuzzi. Sliding glass doors in master open to a deck and large backyard. Wake up to the sound of water lapping at the property’s edge. The second floor offers 3 bedrooms (one with a private bath) and 1 additional bath. An unexpected surprise is the home’s second floor workout area with stationary bike, weights, weight bench and television. Supplying linens, towels and all the comforts of home. Kayaking, fishing, boating, ecotours, antiques, horseback riding or just relaxing around the fire pit watching the sunset and reconnecting with family and friends.

4 – Park Place – Comfy Condo Close to Beach – 10 Miles

Spacious Living Room and DIning Area

Park Place – Comfy Condo Close to Beach

Located a walk away from Kiptopeke State Park, 7 miles from the Historic Town of Cape Charles and 3 miles from one of the Modern Wonders of the World, The Chesapeake Bay Bridge Tunnel, Park Place offers the comforts of home and the location for easy day trips to Virginia Beach, Williamsburg, and Chincoteague.  Park Place has been recently renovated by the new owners and shows pride of ownership. The Living Room easily seats 6 and all can watch the large flat screened TV offering a cable package including MLB. The dining Area is spacious with seating for 6 and the fully equipped kitchen finishes out the open concept living area so you’re never cut off from the rest of the family.

There are 2 first floor bedrooms and 1 full bath which makes it convenient for the elderly or small children to maneuver.

Upstairs is the ultimate Master Bedroom Suite offering a king size bed, mater bathroom with jetted tub, separate shower and dual sinks. A private balcony awaits you.

With close access to Cape Charles, you have a wonderful public beach, restaurants, shopping, jet ski rentals, theatre, library, ice cream shop, gourmet food stores and specialty shops. Artists abound on the shore and their work is amazing.


5 – Bay Dunes – ONLY 2 WEEKS LEFT THIS SUMMER! – 4 Miles

Steps away from private beach access


Plenty of room and privacy in this extra-large luxury home in the desirable Bay Ridge community, steps from the best private beach on the Eastern Shore.

  • Five bedrooms, each with private full bath and flat screen TV
  • Den with queen sofa bed and large flat-screen TV
  • Spacious family entertainment area
  • Open gourmet kitchen with large island, breakfast bar, 2 dishwashers and 2 ovens
  • Dining room with large dining table
  • Powder room
  • Two expansive decks w/deck furniture
  • Screened in porch
  • Beautiful wooded lot with Chesapeake Bay views
  • Two outdoor showers with dressing rooms
  • Enjoy the Bay Ridge community, with private pool, covered picnic area and tennis courts.


Most of our properties have 4 to 7 night minimums stays during peak season (June 18 to September 9). If you have a special need, don’t hesitate to contact us. 

This beachfront home is waiting for a large family to enjoy the 5 bedrooms plus Den, 5.5 bathrooms, spacious entertaining area and a large gourmet kitchen. In addition, enjoy the expansive decks and screened in porch with views to the Bay. Walk to the end of the driveway and see the boardwalk leading to the communities private beach. Walk to the end of the block and enjoy the community pool. Take advantage of 2 convenient outdoor enclosed showers to shake the sand or chlorine off before entering the home.

6 – PET FRIENDLY-Barefoot on the Beach, 2 Blocks to Beach 2 Blocks to Town – 500 Yards

Barefoot on the Beach-2 BLOCKS TO THE BEACH

PET FRIENDLY-Barefoot on the Beach, 2 Blocks to Beach 2 Blocks to Town

People watch from the open front porch of this Eastern Shore style 3 bedroom, 1.5 bath home. 2 BLOCKS TO THE BEACH AND 2 BLOCKS TO TOWN. Perfect to enjoy coffee in the morning or relaxing after a hard day at the Beach!

The large foyer welcomes you to the Living Room with a large sectional sofa and flat screen TV and DVD player. The Dining Room has room for 6 and the oversized kitchen has additional seating for 4. The laundry room and half bath are located on the first floor as well with access to the backyard.

Upstairs are 3 good size bedrooms offering 1 King, 1 Queen and 2 Twins. There is a full bath offering a tub/shower combination and plenty of space to keep your essentials.

Outside is a hot/cold shower to wash off the Beach before you enter the house. Outdoor dining is provided on the front porch as well as the back patio along with a gas grill.

Enjoy the convenience of Dining, Shopping, Kayaking, sailing, fishing, boating, and golfing all without leaving town. Rent a golf cart during your stay (Book early as they sell out quickly!).

If you do explore the area, Cape Charles is a convenient place to day trip to Chincoteague, Virginia Beach, Busch Gardens and Williamsburg.



7 – Indigo Cottage – 700 Yards

Indigo Cottage

Newly renovated with all new kitchen and baths. Only two blocks to the town beach and a little over 1 block to the town park, this new listing is beautifully furnished. In addition to the attention to interior details, there is a big gas grill and picnic table in the back yard  as well as an outdoor shower.

There is a bedroom with a king bed, one with a queen bed and a third bedroom the has a bunk bed plus a twin bed and a TV for the kids.

Only 4 blocks to the main street with shops and eateries, it is an easy walk or you can rent a golf cart to get around town (they’re legal in Cape Charles)

The very kid friendly beach is never overcrowded like many east coast beaches so it makes for a relaxing time. Bike rentals are also available and if you happen to have a trailerable boat, there are great launch ramps at the town harbor and plenty of transient docking. 

8 – Bay Cottage – 200 Feet to The Beach – 300 Yards

Across from the beach. Only about 200 feet.

Bay Cottage – 200 Feet to The Beach

The most affordable BEACHFRONT vacation rental in Cape Charles/200 FEET FROM THE BEACH with access walkway over the dunes sits BAY COTTAGE. Step out the front door and be on the white sand beach in less than a minute. The cottage sleeps 8 with 3 bedrooms and two baths plus a queen size sofa bed in the living room. The Living Room and Sunroom face the Bay with spectacular sunsets. The dining room seats 6+ and conveniently located right off the modern kitchen. A large patio offers comfortable outdoor seating and has a full size gas grill. The property offers off street parking for your convenience.

Bedrooms 1 and 2 offer queen beds and bedroom 3 offers two twin beds. As mentioned, there is a queen size sofa bed in the living room and a portable pack and play play pen. The cottage works well for a family or a group of friends to spend a beach vacation in a charming town where everything is within walking distance. 

Cape Charles offers an array of dining and shopping. Charter fishing, kayaking and eco tours let you experience the amazing ecosystem this area offers. Bring your boat and launch off the public boat ramps of Cape Charles, Kiptopeake or Oyster. Rent a golf cart while your here as Cape Charles is golf cart friendly.

If you feel like venturing out of town, Cape Charles is conveniently located for great day trips to Chincoteague, Virginia Beach, Busch Gardens and Williamsburg.

Come back and watch the most amazing sunsets right out your front door!


9 – Neptune’s Castle – 4 Miles

Neptune’s Castle

4+ bedroom, 3.5 bath sleeps 10 with room to spare. Located a few hundred feet from the private beach entrance walk and within sight of the community pool, this completely modern brick home is the perfect combination of location and comfort. The kitchen features all new appliances, granite counters and plenty of seating. There is additional seating in the adjacent open hangout room as well as a desk and flat screen TV. Just off the kitchen is a sun room that opens onto the patio with a built in gas grill.

The living room has 4 recliner sofas and a 36″ flat screen TV. Also on the first floor is a small den with a queen size sofa bed. 

There is a half bath on the first floor as well as a full bath in the tiled garage that will serve as a game room. The owner plans to put several games there including air hockey.

There are 4 bedrooms on the second floor, a king bedroom with a TV, a queen bedroom and two bedrooms that each have two twin beds. This is a great house for kids.

Located within a few minutes drive of Cpae Charles with its restaurants and shops. It is close to the Chesapeake Bay Bridge Tunnel allowing for day trips to Virginia Beach and the historic triangle of Williamsburg-Jamestown-Yorktown. 

Best of all though, it is a quick stroll to the best beach on Virginia’s eastern shore and it is a great swimming beach for kids.

10 – Bayview Point-BEACHFRONT – 5 Miles

Bayview Point Front View

Bayview Point-BEACHFRONT

3Nestled among tall pines, Bayview Point is a contemporary French Provincial with more than the comforts of home.
Large enough for your family and a few friends too! From the fabulous great room with it’s soaring ceiling and walls of glass to the impressive gourmet kitchen with granite counter tops and all the tools available to create your favorite dishes. The first floor Master Bedroom is a private oasis featuring a King size bed, Master bath and comfortable sitting area to read the latest best seller. Let the kids enjoy their own space right off the great room with enough seating for 8 and large flat screen TV.
There are 4 bedrooms on the second level. The second floor King bedroom offers an adjoining room with a trundle bed and its own mini kitchen. Make a pot of your favorite coffee and walk onto the covered balcony overlooking the bay. The 3 additional bedrooms and 2 full bathrooms complete the accommodations. The house also offers access to the community pool located within Bay Ridge.




Welcome aboard Sail Cape Charles! If one of our cruises doesn’t meet your needs, let us know how we can create one that does.

Enjoy an evening under sail aboard S/V StewardShip out of Cape Charles, Virginia. Experience the fresh breezes that the lower Chesapeake Bay has to offer while the sails fill and pull you and your crew toward no particular place. Perhaps a few dolphin will play with us along the way as we pass the remains of the Cherrystone Bar Light and the Old Plantation Flats Lighthouse.

2011 Rates**

Two Hour Sail $50 per person
Three Hour Sail $65 per person
We will be happy to entertain your special cruising needs!

S/V Stewardship carries a maximum of four passengers.



Tourist Attraction