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 – WHY STAY IN A HOTEL WHEN YOU CAN ENJOY A LOFT STYLE APARTMENT – 1 Miles

WHY STAY IN A HOTEL WHEN YOU CAN ENJOY A LOFT STYLE APARTMENT

In the heart of downtown Cape Charles, a modern loft style apartment with all the comforts of a 4 star hotel suite! The best part is this property is DOG FRIENDLY!

Upon entering, you’ll see the amazing job the owners did in designing the space. The living room, dining room and kitchen flow into one another without being the least bit crowded. Not shown is a screened in porch to the right side of the front door.  This will be built in the Spring. The window in the kitchen can be opened as a pass thru so you may enjoy an outdoor meal or simply drinks at the end of the day.

The Master Bedroom offers a King size bed and vanity area. The Master Bathroom with an enormous walk in shower, separate water closet and oversized walk in closet lies just off the bedroom.

As a bonus, there is a multi purpose room. The vintage work desk is large enough to spread out a laptop and files (if you must bring work with you). The laundry area is also located here for your convenience. In looking at the photo’s, this does not look like a laundry room. Again, the owners have put quite a lot of thought into the design.

The property offers plenty of parking. If you have a boat or motor home, there is room enough for both! A public boat ramp is available at the town harbor with direct access to the Chesapeake Bay.

Cape Charles is conveniently located at the southern most point on the Eastern Shore of Virginia. There are a number of restaurants, bars, ice cream shops, unique shops, bait and tackle, library, pharmacy, doctor’s office, hardware store. Food stores and additional restaurants are a 2 mile trip to the highway. 

If you want to explore more of the area, Cape Charles is poised for day trips to Chincoteague to see the wild ponies and ocean, Williamsburg and Busch Gardens to name a few.

 

 

 

2 – 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.

3 – PLAN YOUR FALL GETAWAY-FALL RATES WITH SUMMER WEATHER!! – 4 Miles

Steps away from private beach access

PLAN YOUR FALL GETAWAY-FALL RATES WITH SUMMER WEATHER!!

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.

4 – Laughing Gull-PET FRIENDLY Sleeps 6-8 One and one half blocks to Beach – 300 Yards

Living Room with Flat Screen TV and DVD player

Laughing Gull-PET FRIENDLY Sleeps 6-8 One and one half blocks to Beach

Located one block to the beach and right in the center of town. Leave your car and walk to shopping, restaurants, beach and fishing pier. Located on the second floor (elevator building), this Condo has everything you will need for the vacation you have been waiting for. Offering 2 bedrooms and 2 full baths, the home sleeps 6 to 8 comfortably. The Master Bedroom has a Queen size bed and the second bedrooms offers 2 sets of bunk beds. The living room offers a Queen size sleeper sofa.

Enjoy the fully equipped kitchen just in case you want to cook. The Dining Room seats 6 comfortably.

The cozy living room offers a DVD player and  flat screened TV. Access to the back deck is off the Living Room.

The Condo has access to the REAR rooftop deck offering town views. Walk 1 and 1/2 blocks to the beach to watch the sunset and celebrate the end of the day.

Conveniently located for day trips to Chincoteague, Virginia Beach and Williamsburg. Brochures will be available in the Condo to help you decide what to do each day.

THIS HOME HAS A LIMIT OF 1 DOG

5 – Sunset Bay – 1 Miles

Welcome to Sunset Bay

Sunset Bay

Our newest vacation rental with amazing views of the Chesapeake Bay. Enter the spacious foyer and up one flight to an incredible open concept Living Room, Dining Area and Large Kitchen with all the bells and whistles. The living room is spacious with wraparound couch and lounge chairs facing the large screen TV and fireplace. Looking west out the sliding glass doors is a full balcony and an enclosed screened in porch looking out over the Bay and beach. 

The Dining Area can seat 10 and the Breakfast Bar an additional 2 guests.

The kitchen is fully equipped and offers dishwasher, disposal, microwave, wall oven, cook top, serving dishes, pots, pans, utensils

There are 2 downstairs bedrooms. The master with master bath and a second bedroom with access to its own bathroom.

On the main level a third bedroom offering bunk beds. A single upper and a double lower. The den offers a queen sleeper sofa.

The third level offers amazing views as well as a balcony to relax and enjoy the sunsets. A wet bar and a mini fridge complete the loft.

The home is located in the Historic town of Cape Charles in the resort community of Bay-Creek.

This home enjoys access to a community pool and tennis court, two signature golf courses (fee charged), private beach as well as the town beach.

Plenty of shopping, restaurants, fishing, kayaking, eco tours, antiquing, horseback riding, jet skiing, bird watching, 

Cape Charles is poised for great day trips to Chincoteague, Virginia Beach, Williamsburg and Busch Gardens.

We require a minimum stay of 3 nights over Memorial Day and Labor Day weekend.

 

6 – Huntington Farm – NEW LISTING – Great Gathering Place and Wedding Venue – 3 Miles

Aerial Photo

Huntington Farm – NEW LISTING – Great Gathering Place and Wedding Venue

Huntington Farm is a fantastic 14 acre gathering place for a large family or multi-family group as well as an excellent waterfront location for weddings and events. Situated along Cherrystone Creek just 5 miles from the town of Cape Charles, it dates from the 1600’s when it was known at the Huntingdon Farm. Somewhere along the way, the “d” was replaced by a “t”  and hence the name Huntington. It is an ideal setting to get away from it all but still close to the great shops and restaurants in the town.

Built in the 1600’s and fully restored, it has a huge living area including a formal living room, formal dining room, a large modern kitchen and a family room with large picture windows looking out on Cherrystone Creek. The second floor sleeping areas include three bedrooms with en suite baths. Bedroom 1 has a king bed, bedroom 2 has a queen and bedroom 3 has two sets of bunk beds. There is also a sleeping/sitting room that has two day beds (twin size). 

7 – Dryden House-Beachfront Historic Home w/ AMAZING WATER VIEWS – 300 Yards

Front View

Dryden House-Beachfront Historic Home w/ AMAZING WATER VIEWS

The Dryden House is offered as a weekly private rental after an extensive 18 month historical renovation. Enjoy all of the historical charm and updated amenities that this grand home has to offer. You can step back in time and step off your porch into the dunes of the Chesapeake Bay.

This 1912 historic private home known as the Dryden House is located within a registered historic district, known as the Sea Cottage Addition of Cape Charles, which is comprised of an intact grouping of architecturally significant commercial and residential buildings constructed between 1850 and 1915 that display a variety of styles and types of architectural ornamentation popular during this era. The Dryden House is unique due to its prominent size and central location upon Bay Avenue just steps from the beach and only two blocks from the town’s charming business district.

This three-story Victorian has an extensive wrap around porch, with a porte cochere and was constructed by E. T Dryden who built other notable homes nearby. This beachfront home features Bay views from almost every room in the home including all second floor bedrooms with a water view. There are two full baths on the second floor and a full bath on the first floor with a convenient washer and dryer. Before you come into the home from the beach, you can wash away the salt and sand in the outdoor shower.

The large kitchen has new high end appliances, with two full size sinks spacious enough for two chefs and a separate beverage center and coffee station assuring you will not be bumping elbows with your guests! The oversized dining room features an expandable dining table that can easily seat 12 plus for meals. Formal paneled pocket doors make this floor plan as open or private as you desire. 

Finished third floor family room with large flat screen TV, DVD, soundbar, Netflix and Amazon Prie. Wii with balance board and a good selection of Wii games. A selection of over 50 movies for both kids and adults. A full size foosball table completes the game room for when your’re feeling competitive. There is three zone air-conditioning to keep you comfortabel on those hot days and nights.

The town gazebo and free fishing pier is to the left of the home and the extensive town walkways make this ideal for strolling or catching an evening horse and carriage ride on the Bay. Sunsets are nightly!

PETS WILL BE CONSIDERED ON A CASE BY CASE BASIS.

IF ALLOWED, THE NON-REFUNDABLE PET FEE IS $260.00

WEEKLY RENTALS ONLY DURING PEAK SEASON.
 
 
 
  

8 – Pelican Watch – 1 Block to Beach, Kayak Included PET FRIENDLY – 700 Yards

ONE BLOCK TO BEACH,  BAY VIEWS, KAYAK INCLUDED

Pelican Watch – 1 Block to Beach, Kayak Included PET FRIENDLY

This is a charming 1000 sq ft cottage with bay breezes. You are a 600 foot walk to the bay beach and a few blocks to the restaurants, shops, harbor, fishing pier, theater and marina. This is the quiet end of town and the yard is fenced in so pets are considered. 3 bedrooms, 1 downstairs with queen bed, 2 upstairs bedrooms, one with two twin beds and the other with one twin bed. 1 bathroom downstairs with tub/shower combo. Comfortable airy living room. Small well-equipped kitchen and separate dining room. Utility room with washer/dryer.

The steps to the second floor are on the steep side. Elderly or very small children should be monitored.

Gas grill and 2 person kayak in yard. Wifi Internet/DishTV/DVD/CD. Romantic, cozy and clean. On street parking for car and boat. Charter a fishing boat or walk to the pier and fish for free. Sunsets are spectacular down on the beach. The house is on the north end of the beach, and we love watching the seagulls and pelicans and other shore birds perching on the pilings from the old ferry dock.

9 – Barefoot on the Beach – 500 Yards

Barefoot on the Beach-2 BLOCKS TO THE BEACH

Barefoot on the Beach

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.

 

 

10 – Chesapeake Dream – Restored Victorian 1 Block To Beach – 400 Yards

Stately Victorian 4 homes from the beach

Chesapeake Dream – Restored Victorian 1 Block To Beach

You must enter the dates of your requested stay in order to get correct pricing. If you do not enter your dates, the prices shown do not include taxes and fees that are charged on a per stay basis.

Recently bought and already a showpiece. The owners have furnished their home with the comfort of their guests in mind. Located a short 1 block to the beautiful Cape Charles town beach, this home offers 4 bedrooms, 3.5 baths, office, 2 dining rooms, a spacious modern kitchen with plenty of prep area, a convenient laundry room off the kitchen and both side and back doors for convenience. The second level offers 3 spacious bedrooms and 2 full baths. The third level is a true hideaway. Great for kids and also wonderful for a parents retreat. Spacious and private with an en-suite full bath.

Sit on the covered wrap around porch in comfortable rocking chairs and enjoy people watching, catching up on a good book or a midday nap. When your rested from a hard day at the beach, walk the two blocks into town for restaurants, shopping, homemade ice cream (so good!) and watching the sun set over the Bay. We celebrate sunsets, as one is more beautiful than the next.

Cape Charles is golf cart friendly. Leave your car at the house and explore the town and Bay-Creek from your golf cart rental. From chartering a boat, to taking a guided kayak tour, horseback riding, winery tours, eco tours or antiquing , you’ll remember this vacation for years to come.

Map

 

 

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.

 

Details


Category:
Tourist Attraction
Phone:
973-479-3346
Email:
SailCapeCharles@yahoo.com