Dockside Dreams

$115.00 - $439.00 /Night
Average Rating

Address: 37531 Bayside Drive Location: Greenbackville Type: House Area: 1728 sq. ft.
3 Bedrooms 2 Baths Sleeps 6 Pets Allowed Parking Spaces: 4 Linens Provided
Bedroom 1
1 Queen
Bedroom 2
1 Twin Bunks, 1 Pyramid Bunk
Bedroom 3
1 Queen
Life takes you down many paths, but our favorite ones always lead to the Beach….

There’s nothing like the smell of salt in the air and a warm breeze through your hair - the complete feeling of freedom that engulfs you the moment you know your Vacation is about to begin. And that’s what you’ll find at Dockside Dreams in fabulous Captain’s Cove Golf and Yacht Club - freedom, peace, and water, water, everywhere!

Captain’s Cove is one of the best kept secrets on the Eastern Shore of Virginia. Sitting directly on the Chincoteague Bay, just 25 short minutes by car or boat to Chincoteague and Assateague Islands, where our Wild Ponies roam free, it is pure Paradise. Looking for some OC excitement? Ocean City, MD is a short 45 minute drive away. Here, life takes a slower pace - sipping wine as you watch the sun sink into the Chincoteague Bay, or the joy you feel watching the kids catch Crabs off the dock. THIS is what Vacation Dreams are made of. More great news? You can bring your well-trained dog (2 Max) with a $100 Pet Fee!

Dockside Dreams sits in a unique location in the Cove - the “Point”. As you drive down Bayside Drive, you will have water on 3 sides - almost like it’s your own little Island! Sitting Canalfront, you not only have gorgeous Canal Views, but great open Views of the Chincoteague Bay! Be sure to bring the Boat, as you can drop it in at the Marina, and tie up in your own backyard! The kids - and the kid in you - will have a blast fishing and crabbing in the Canal, or maybe just tie up a tube and float!

You’ll love relaxing in the Living Area and kicking back with Free WiFi and Flat Screen Streaming TV. Sink into the comfy furnishings after a fun-filled day at the Beach, and share stories of the day’s adventures. Wonderfully laid out with so many nooks and crannies to relax in, you’ll never feel crowded! And we just love the warm and inviting Vaulted Pine Ceiling. Follow the spiral staircase up to the Loft, and you’ll find a great space for the kids to have some quiet time watching a movie. There’s also a Futon allowing for another sleeping option if needed (Occupancy of 6 strictly enforced). Step out onto the Upper Deck to take in breathtaking Views, or perhaps relax in one of the Adirondacks and take it all in.

Just off the Living Area, you’ll find the Well-Stocked Eat-in Kitchen - light, bright, and open. With all the comforts of home, mealtime will be anything but a chore! Wander out to the Sunroom and Screened Porch, which lines the entire back of Dockside Dreams. Begin and end everyday watching Herons, Eagles, and Egrets fish for their morning meal.

Dockside Dreams sleeps 6 in 3 Bedrooms more than comfortably. Bedroom 1 is a Master with a comfy Queen Bed and access to the Bayside Deck. Slip out to stargaze while the rest of your family slumbers. The Private Master Bath has a Tub/Shower Combo and whimsical Coastal Decor. Bedrooms 2 and 3 are tucked on the other side of the house, plus another Full Bath with Tub/Shower Combo. Bedroom 2 sleeps 5 with a Twin Bunkbed and Pyramid Bunkbed (Twin over Full), and is dressed in Nautical Blues and Reds. Down the Hall, Bedroom 3 has another Queen Bed and also has access to the Bayside Balcony.

As for the outside living, Dockside Dreams is a veritable Waterfront Playground! The perfect place to launch your Kayaks and Paddle Boards, you’ll love playing in the calm Canal waters. Access to the Bay is literally around the bend, so bring the Boat and Fishing Gear - our waters are teeming with life.

Captain’s Cove is loaded with amenities - a Golf Course, Indoor Pool, 2 Outdoor Pools - 1 Bayfront with Tiki Bar, Fitness Center, Playground, Restaurant, and Snack Bar. Guests may purchase Amenity Passes for the pools by the day or the week at a minimal fee ($10/pp per day or $50/pp per week). More of a beach person? One of the most gorgeous, cleanest beaches in America, Assateague Island National Park, is only 20 minutes down the street, or take your boat to one of our awesome sand bars for your own private slice of Paradise.

Captain's Cove does not allow arrivals or departures on Sundays. Pool/Amenity closures possible due to covid and Amenities cannot be guaranteed. Please check with our office for current status.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs are welcome with $100 Pet Fee per Dog - 2 Dog Max. Dogs MUST be current on Flea/Tick Preventative ; Immunizations. No Cats.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

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  • Water Parks
  • Assateague National Seashore
  • Playground
  • Museums
  • Festivals
  • Churches
  • Autumn Foliage

Beach Equipment

  • Crabbing Equipment


  • Streaming TV/Roku Only
  • Television


  • Dryer
  • Washer
  • Private Living Room
  • Laptop Friendly
  • Heating
  • Hair Dryer
  • Air Conditioning


  • Free Parking
  • Snack Bar
  • Balcony

General Indoor Amenities

  • Wireless Internet

Home Safety

  • Fire Extinguisher
  • Smoke Detector


  • Oven
  • Range
  • Full-Sized Refrigerator
  • Toaster/Toaster Oven
  • Dishwasher
  • Pots & Pans
  • Kitchen
  • Microwave
  • Dishes & Silverware
  • Drip Coffee Maker


  • Sight Seeing
  • Shopping
  • Miniature Golf
  • Scenic Drives
  • Walking
  • Boating
  • Beach Combing
  • Crabbing
  • Wildlife Viewing


  • Fitness Center


  • Bayside
  • Water View
  • Resort

Location Type

  • Waterfront


  • Garden or Backyard
  • BBQ Area

Outdoor Amenities

  • Screened-In Porch
  • Boat Dockage

Outdoor Grill

  • Gas Grill


  • Heated Pool
  • Indoor Pool


  • Shared Outdoor Pool


  • Community Pier
  • Private Pier
  • Flex-Stay Home
  • Fireplace
  • No Smoking
  • Linens Provided


  • Swimming
  • Basketball Court
  • Equestrian Events
  • Fishing - Bay
  • Golf
  • Pier Fishing
  • Cycling


  • Away From It All
  • Family
  • Sports Activities
  • Romantic
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