Sail Cape Charles
Sail Cape Charles
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!
WEEKLY RENTALS ONLY DURING PEAK SEASON.
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
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.
Formerly know as the Quarter Master, Family Tides is a fully restored and renovated Victorian home dating from 1928 and one of the structures contributing to the Historic District classification of Cape Charles. Located just a short walk from the public beach and 1 block from the main street shops and eateries, Family Tides sleeps as many as 16 in beds. Ideal for large families or multi-family groups, it has multiple living areas that allow evryone to have some space .
There are two master bedrooms with queen beds, each with en suite baths. Two additional bedrooms, each with two sets of bunk beds that offer double beds on the bottom and twin bedding on top. The two bunk rooms are served by a Jack and Jill bath. In addition there is a full bath on the first floor.
A large fully equipped kitchen affords eating space in addition to the dining room. The middle of the house includes the dining room and a large, comfortable sitting area with flat screen TV. On either side of the entry hall are two smaller living areas, one with comfy seating and TV and the other suitable for the kids.
When you want to enjoy the out of doors, there is a full width front porch with seating. A real gem is the fenced back yard with a large patio that has a dining table and built in benches all around. The storage shed houses several adult and childrens bikes as well as some beach equipment including beach chairs and carts for transporting gear to the beach. The outdoor storage trunks hold plenty of sand toys for the little ones.
For large groups or folks who just like a lot of space, Family Tides is one of the best options in Historic Cape Charles.
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.
PLEASE ADHERE TO THE NO PET POLICY.
IF YOU NEED TO MAKE ARRANGEMENTS FOR BOARDING, WE WILL BE HAPPY TO HELP.
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.
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 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.
Wonderful 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.
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.
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.
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.
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