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 – The One-Eighty – Brand New 4 Bedroom Beach House – 5 Miles

The One-Eighty – Brand New 4 Bedroom Beach House

The One-Eighty is a brand new beach house located in the Bay Ridge area of Sandhill with direct access to the best beach in the Cape Charles area and includes pool and tennis court access.

The home is nearing completion and will be available for rent immediately after Memorial Day Weekend.

This luxuriously constructed home includes 4 bedrooms, three baths and sleeps 10. There are both first and second floor decks from which to enjoy the beautiful surroundings.

With multiple TVs, WiFi and an outdoor shower, this is going to be a great place for families to spend a beach vacation with the town of Cape Charles with its shops and restaurants and Nicklaus and Palmer golf courses only 8 to 10 minutes away.

2 – 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.

NEW THIS YEAR-OUTDOOR SHOWER

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.

3 – 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 is conveniently located off the modern kitchen. A large patio offers comfortable outdoor seating with 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. 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 you’re 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!

 

4 – THIS PROPERTY IS NO LONGER AVAILABLE. – 300 Yards

Front View

THIS PROPERTY IS NO LONGER AVAILABLE.

THIS PROPERTY IS NO LONGER AVAILABLE

CANCELLATION POLICY:  For any cancellation that is more than 60 days prior to the check in date, there will be a 100% refund. For any cancellation that is between 45 and 60 days prior to the check in date, there will be a 10% cancellation fee. If the cancellation occurs less than 45 days from the check in date, no refund will be made unless all or part of the reserved period is re-booked, in which case a refund equal to the amount of the new booking will be made less a $100.00 cancellation processing fee. 

 

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 Prime. 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!

THIS PROPERTY IS PET FRIENDLY!

WEEKLY RENTALS ONLY DURING PEAK SEASON.

 
 
 
  

5 – AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1 Block to Town – 400 Yards

Victorian Beach House 2 Blocks to the Beach

AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1 Block to Town

AT LAST is the perfect name for this Victorian Beach House. The owners have lovingly brought the home back to life and now want to share it with you. This PET FRIENDLY home is 2 blocks to the Beach, 1 block to Town and 2 blocks to the 5 acre Town Park. Park your car for the week and explore the Town on foot or in a rented golf cart. Cape Charles is golf cart friendly.

The home offers 3 bedrooms, 2 full baths, living room, dining room, family room, kitchen and laundry room. A large fenced in back yard with mature growth trees and plantings offer a cozy setting as your sitting around the fire-pit.

Cape Charles offers great restaurants, shopping, gourmet markets, art galleries, theater, pharmacy, medical services and library. No license is required for the Town fishing pier so bring your polls.

Do you like horseback riding, antiquing, fishing, sailing, jet skiing, kayaking, windsurfing?. We have all that and more. Bring your family on a vacation they will remember. We know you’ll be back.

6 – Chesapeake Dream – Restored Victorian 1 Block to the Town Beach! – 400 Yards

Stately Victorian 4 homes from the beach

Chesapeake Dream – Restored Victorian 1 Block to the Town 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.

7 – By The Bay – 800 Yards

BY THE BAY

By The Bay

Vacation BY THE BAY! 4 blocks to the Beach and 1 block to downtown Cape Charles. This 4 bedroom 2 bath Eastern Shore style home is our newest listing. Offering a first floor Master Bedroom with King Bed. Spacious living room and dining room with an open concept feeling. A fully equipped kitchen and first floor laundry area. Access to the fully fenced back yard, perfect for pets.

Upstairs are an additional 3 bedrooms and full bath. Offering 1 king and 4 twins. The home offers 2 zone air conditioning and heat.

An open front porch with seating for 6+ is perfect for your morning cup of coffee or relaxing after dinner.

Enjoy our Town Beach that runs the entire length of downtown and newly expanded. Fish off of the Town Fishing Pier next to the Beach (no license required)

Golf cart rentals are available for your stay. Cape Charles is golf cart friendly so leave the car at home and stroll around town in your cart. The home is located so that walking to town and beach is quite easy too!

Enjoy our many restaurants in town and also 5 to 10 minutes out of town. Our Ice Cream shop has won numerous awards and is open 6 days a week. Enjoy our local shops with a great variety of everything you may need or have forgotten to take, to enjoy your vacation.

Wine tasting is every Friday and Saturday in Gull Hummock, a gourmet wine and cheese shop and more. From Clothing, Jewelry, Spa Treatments, Art Galleries, Specialty shops, Hair Salons, Banking, Library, Medical Center, Pharmacy, Children’s playground, Central Park (a 5 acre Park in the center of town), you won’t need to leave town

In the event you do, Cape Charles is poised for easy day trips to Chincoteague (see the wild ponies), Virginia Beach, Busch Gardens and Williamsburg.

8 – Beachcomber – 400 Yards

Front Angle

Beachcomber

Beachcomber is ideally located just 1 block from the Cape Charles Town Beach and two blocks from Mason Avenue where the shops and eateries are located. It takes up the entire first floor level of  this home. The owners use the top two levels as their vacationj home. It has a bedroom with a king bed and the second bedroom has a queen bed and ensuite bath, . A bright breakfast room and a completely modern kitchen open to the living area making for a great spot to hang out with family and friends. There is also a queen size futon in the living room that can accomodate two more for a total of six guests.

The huge columned porch adds to the fun of this spot with the beach dunes in sight from the porch. Step off the porch and it is only about 600 feet to the beach. Most of the shops and several eateries and bakeries are within a 5 block stroll as well as a top 10 rated ice cream shop, a candy store and a gourmet food shop with regular free wine tastings. 

 

9 – 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

10 – BayCation – Sleeps 8-TWO blocks to the beach! – 700 Yards

Four Square 2 Blocks to the Beach

BayCation – Sleeps 8-TWO blocks to the beach!

Situated on a double lot, this gorgeous historic home is just two blocks from the beach, two blocks from the park, and four blocks from town!

Pottery Barn Grand furniture in the spacious living room, a welcoming foyer, and formal dining room. 

Upstairs are 4 bedrooms; one with TV, and a full bath. One King, 2 Queen’s and 2 twin beds.

Granite countertops, pendant lights, and dishware: this Kitchen offers all the amenities 

For dining al fresco, choose the expansive  furnished porch or oversized backyard. The porch offers bay views and breezes with Elecrtical outlets and stained glass lighting to enhance your porch experience .Enjoy morning coffee, evening cocktails, and our famous sunset!

Oversized back yard is fenced and privacy landscaped. Enjoy the garden seating and table, relax by the fire-pit, and grill while watching the fish in the koi pond with a life-size heron sculpture. Play with the included games, badminton, boogie boards, and available beach chairs. 

Rinse yourself off in the Outdoor Shower with hot and cold water. Enclosed for privacy.

Cape Charles location is poised for great day trips to Chincoteague, Williamsburg, Busch Gardens and Virginia Beach. The town offers a five acre Central Park with a children’s playground, 2 Marina’s, public boat dock, fishing pier (no license needed), shopping, restaurants, library, ice cream shop, medical facilities, ATM, pharmacy and 2 miles on the highway is Food Lion grocery store.

BayCation is sure to please, rejuvenate, and become a family favorite!

Check in and Check out are Saturday to Saturday

 

 

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