Calypso by Seaside Vacations & Sales

Photo gallery for Calypso by Seaside Vacations & Sales

A coastal residential area with houses along a marina.
A large house with a swimming pool, a covered patio, and a view of the water.
A covered porch with a ceiling fan, white railings, and a view of a river and houses.
A modern kitchen with white cabinets, a black granite countertop, and stainless steel appliances. There are white chairs around the island and a view into the adjacent living area.
A two-story house with a front porch and a staircase leading to the second floor.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Top-rated for value
    Guests love how much they get for what they pay.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 84 bedrooms10 beds

Popular amenities

  • Heated pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Greenbackville, VA
  • Place, Captain's Cove Golf and Yacht Club
    ‪1 min drive‬
  • Place, Chincoteague National Wildlife Refuge
    ‪32 min drive‬
  • Place, Assateague Lighthouse
    ‪34 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪52 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

1

1 Queen Bed

2

1 Queen Bed

3

4 Single Beds

4

4 Single Beds

3 bathrooms, 1 half bathroom

Full Bath 1

Towels provided · Bathtub or shower · Toilet

Full Bath 2

Towels provided · Bathtub or shower · Toilet

Full Bath 3

Towels provided · Bathtub or shower · Toilet

Half Bath

Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

Calypso by Seaside Vacations & Sales

Calypso - Dance to the Song of the Sea.....

You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 Bedroom/3 Full and 2 Half Waterfront Dream Home has something for everyone in the family. Located Canal Front on the Chincoteague Bay, this statuesque home is a Water Lover's delight, and is only 20 short minutes by car or boat to Chincoteague & Assateague Islands, where our wild ponies roam free. Looking for some OC excitement? Ocean City, MD is a short 45 minute drive away. Have the best of everything, right in the heart of the Eastern Shore!

Beautiful Calypso sleeps 8 more than comfortably. This Coastal Dream Home will take your breath away. As you drive through Captain's Cove, taking in the smells of whispering pines and salty, sweet air, you will feel a million miles away from the "real world". This is just what you've been waiting for! Will you hear traffic on the busy highway you drive every day? No way. Will you be checking into a busy hotel? Not a chance. You will arrive at this lovely home and find a place of peace, serenity, pure beauty, and tons of fun!

This majestic Home is 3 Levels of pure Luxury with Decks and Porches in every location to take in nothing but amazing Views. As you enter Calypso, you'll be swept away by Tropical Colors & Decor that will make you leave your troubles at the door. This one-of-a-kind Home was designed with a Reverse Floor Plan, maximizing Views from your Living Area and Kitchen, but trust me, they're sigh-worthy on every level. Upstairs you will find gleaming Bamboo Floors and Sunny Yellow Walls opening to a Wall of Windows facing the Canal and Chincoteague Bay. With soaring ceilings and an Open Floor Plan worthy of Family Vacation time together, you'll never want to leave. The comfortable Living Area is furnished beautifully and well-equipped with Free WiFi and Flat Screen Satellite TV. A wonderful Furnished Deck off of this level is a wonderful place to relax with your morning coffee or a glass of wine at day's end as you watch the sunset. Just imagine relaxing while the kids fish and catch crabs right in your own backyard!

The Chef in your Family will adore this well-stocked Kitchen with rich Granite Countertops and every gadget you could want. High-end Stainless Appliances, a breathtaking Tile Backsplash, and Canal Views will make preparing dinner not such a chore after all. Don't feel like cooking on Vacation? Visit the Marina Club in the Cove. There is ample seating for your family between the large Breakfast Bar and spacious Dining Area, and a convenient Half Bath just off the Living Area. Also on this level is a stunning Master Bedroom with a Queen Bed, Flat Screen TV, and fun Tropical Flair. The Master Bath is adorned with Granite and a Tub/Shower Combo.

As you make your way downstairs to the Middle Level, you'll find 3 more spacious Bedrooms! Bedroom 2 is a Junior Master featuring a Queen Bed, colors of Key Lime, and a great Furnished Deck with Views of Swan Gut - a beautiful area teeming with wildlife. You'll love watching Herons, Eagles, and Blue Herons fish for their morning meal. The Junior Master Bath has a Tub/Shower Combo. Bedroom 3 is a fabulous Beachy Blue and has 2 sets of Twin Bunkbeds. Finally, Bedroom 4 is showing off Nautical Navy Bedding on 2 more sets of Twin Bunkbeds, and has access to yet another Waterfront Furnished Deck! Wander to the Lower Level of Calypso, and you'll find a very cool space to hang out with the original Wooden Beams encased in the room. There is a Full Size Futon, another Half Bath, and yet another awesome Screened Porch - a great Hangout for the kids.

Parking for 4 Cars - no exceptions - Occupancy of 8 strictly enforced. 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 ($15/pp per day or $75/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.

No Smoking and No Pets. Linens Included! No smoking/No Pets. Amenity Fees are required for Captain's Cove Amenities.

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4937497
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Greenbackville

Located on the waterfront, this holiday home is in Captain's Cove, a neighbourhood in Greenbackville. Captain Timothy Hill House and Assateague Lighthouse are local landmarks, and some of the area's attractions include Delmarva Discovery Center and Pocomoke Fair Grounds. Wallops Flight Facility and Maui Jack's Waterpark are also worth visiting. Power boating, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Greenbackville, VA

What's nearby

  • Captain's Cove Golf and Yacht Club - 1 min drive - 0.7 km
  • Maui Jack's Waterpark - 30 min drive - 39.6 km
  • Chincoteague National Wildlife Refuge - 32 min drive - 41.3 km
  • Assateague Lighthouse - 34 min drive - 42.7 km
  • Salisbury University - 55 min drive - 65.3 km

Getting around

  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) - 41 min drive

Restaurants

  • ‪Island Creamery - ‬30 min drive
  • ‪McDonald's - ‬34 min drive
  • ‪Amarin Coffee - ‬19 min drive
  • ‪Ropewalk - ‬31 min drive
  • ‪Captain Zack's Seafood - ‬31 min drive

Frequently asked questions

Does Calypso by Seaside Vacations & Sales have a pool?

Yes, this property has an indoor pool and an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Calypso by Seaside Vacations & Sales?

As of 22 Aug 2026, prices found for a 1-night stay for 2 adults at Calypso by Seaside Vacations & Sales on 18 Sept 2026 start from AU$1,378, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Calypso by Seaside Vacations & Sales pet-friendly?

No, pets are not allowed at this property.

How much is parking at Calypso by Seaside Vacations & Sales?

On-site parking is available at the property.

What time is check-in at Calypso by Seaside Vacations & Sales?

Check-in begins at 4:00 PM.

What time is check-out at Calypso by Seaside Vacations & Sales?

Checkout is at 10:00 AM.

Where is Calypso by Seaside Vacations & Sales located?

Located in Captain's Cove, this holiday home is 1.3 mi (2.1 km) from Captain's Cove Golf and Yacht Club and within 9 miles (15 km) of Stockton Park and E.A. Vaughn Wildlife Management Area. Chesapeake Forest and Vaughn State Wildlife Management Area are also within 9 miles (15 km).

About the host

Hosted by Seaside Vacations & Sales

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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