Entire home

Calypso by Seaside Vacations & Sales

Photo gallery for Calypso by Seaside Vacations & Sales

Tropical Calypso in Captain`s Cove is a Waterfront Dream Home.
Multiple Decks & Screened Porches for marvelous Outdoor Living.
This stunning Home sleeps 10 more than comfortably.
Catch your own crabs from your Private Canalfront Dock.
Gorgeous Open Living Area with gleaming Bamboo Floors and Reverse Floor Plan with Living Area on Top Floor.

Reviews

9.2 out of 10
Wonderful
4 bedrooms3+ bathroomsSleeps 8162.7 sq m

Popular amenities

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

Explore the area

View map
Greenbackville, VA
  • Place, Captain's Cove Golf and Yacht Club
    ‪1 min drive‬
  • Place, Ocean City Boardwalk
    ‪57 min drive‬
  • Place, Ocean City Beach
    ‪57 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪47 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.

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

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

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

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 9 Apr 2026, prices found for a 1-night stay for 2 adults at Calypso by Seaside Vacations & Sales on 27 May 2026 start from AU$244, 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).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 35 reviews
Rating 8 - Good. 12 out of 35 reviews
Rating 6 - Okay. 1 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Stacey A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We really enjoyed our stay. The house was great and the location was nice.

We really enjoyed our stay and all the amenities. We really like the year long residents.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 8 July 2023
Thanks so much for choosing to stay with us, Stacey! We're so glad to hear you enjoyed your stay! We hope to have you back soon! :)
Verified

10/10 Excellent

Cindy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Better Than Expected

Beautiful location and home.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 1 July 2025
Thanks so much for taking the time to leave a review, Cindy! We're so glad to hear you enjoyed your time at Calypso, and hope to have you back soon! Best, Tim
Verified

10/10 Excellent

Lisa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house! Perfect for our crew of 7.Only thing missing was a gas grill. There was a charcoal grill though. Loved the deck overlooking the canal. So peaceful! Would stay here again.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 21 July 2025
Thanks so much for choosing to stay with Seaside, and for taking the time to leave a review! We're so glad to hear you enjoyed your time at Calypso, and hope to have you all back soon! Best, Tim
Verified

10/10 Excellent

Gary H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

nice place!

very nice, would stay again. very good communication
Stayed 7 nights in May 2023
Response from VrboOwner on 8 July 2023
Thanks so much for choosing to stay with us, Gary! We're so glad your family enjoyed its visit, and hope to have you back soon!
Verified

8/10 Good

Beth M.

Liked: Cleanliness, check-in, communication, location

Family fun!

Very spacious and clean beach house with plenty of bathrooms and bedrooms for three generations. Common areas and decks were wonderful!
Stayed 7 nights in Sep 2020
Response from VrboOwner on 8 July 2023
Hi Beth! So happy you enjoyed your time at Calypso. We would love to have y'all again! :) Best, Lea Anna
Verified

8/10 Good

Shane H.

Liked: Cleanliness, check-in, communication, listing accuracy

Fit our family’s needs

It was a very nice place to rent. It is a little far from shops/beach but beautiful bay views and nice amenities.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 8 July 2023
Thanks so much for choosing to stay with us, Shane! You really can't beat those bay views! We hope to have you back soon!
Verified

10/10 Excellent

Duwane F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

Calypso was a very nice property overlooking a canal in a quiet but friendly neighborhood, with the home feeling comfortable and extremely spacious. Property management team was informative and helpful.
Stayed 4 nights in Jun 2022
Response from VrboOwner on 8 July 2023
Thanks so much for staying with us, Duwane! We're so glad to hear you enjoyed your stay, and found our team helpful. We'd love to have you back anytime!
Verified

10/10 Excellent

Amy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Place!

This house was perfect for our family getaway! The house was clean and roomy enough for our family! The views were great and all the extras in the garage were perfect for us to enjoy! We will definitely rent this house again if we go back! Oh, the price was amazing for such a beautiful and well maintained home!
Stayed 3 nights in Mar 2021
Response from VrboOwner on 8 July 2023
Amy, We are happy that the house met all of your needs for a great family vacation. We sure hope you come back! Best, Lynn
Verified

10/10 Excellent

Corinne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

House was fantastic! And great location. About 30 minutes from the beach, but the drive is easy. If you are there when they have a scheduled rocket launch you can watch from the balcony or walk down the street. Friendly neighbors and so much to do! Would definitely go here again.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 8 July 2023
Thanks so much for choosing to stay with us, Corinne! So glad you all enjoyed your stay, and were able to experience the rocket launch! We'd love to have you back anytime!
Verified

8/10 Good

Xiaoyan Y.

Liked: Cleanliness, check-in, location, listing accuracy

This vacation house is perfect to hang out with family and friends

Everything about the house is pretty good. Nice and clean, good location, quiet neighborhood. One problem to fix is that the door to the second floor balcony can't be locked. We found it out upon leaving.
Stayed 3 nights in Mar 2021
Response from VrboOwner on 8 July 2023
Xiaoyan, We are glad you enjoyed the visit. Thanks for bringing the issue with the door to our attention. We will get right on that. Come back soon. Best, Lynn
Verified

8/10 Good

Carol P.

Liked: Cleanliness, check-in, communication, listing accuracy

Fun week with the family

The property was as described and enough room for everyone. The kids enjoyed the local pools, but the beach was too long a drive. Beware of the pirates in the basement! The two year old saw them daily!!
Stayed 7 nights in Jul 2022
Response from VrboOwner on 8 July 2023
Carol, Thank you for the review. Sounds like fun was had by all, especially the two year old! Please visit us again. Best, Lynn with Seaside Vacations
Verified

10/10 Excellent

Kim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just as seen.

This place is amazing for the price. Pictures are exactly how the house is. Not outdated. My only complaint is having to pay for the amenities. The host was very responsive and helpful with everything I asked. This would be a great place for a bigger group. Thanks for having us!
Stayed 7 nights in Jun 2024
Response from VrboOwner on 8 July 2024
Thanks so much for choosing to stay with Seaside Vacations, Kim! We're so glad you enjoyed your stay! Unfortunately, the HOA handles all of the amenities themselves, so we have no control over those. We hope to have you back soon!
Verified

10/10 Excellent

Rebecca P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful family vacation

We had a great family vacation! The house was beautiful, very nice amenities, and good restaurant in the community. The kids loved fishing and crabbing right out the back door. It is a bit of a drive to get out and see the area (30 minutes to Chincoteague, 40 minutes to Assateague, 1 hour to Ocean City) but worth the drive. Only complaints are dishwasher left dishes dirty and greasy and the oven task longer than it should to cook meals. Overall, it was a wonderful experience and would stay here again.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 8 July 2023
We're so glad you enjoyed your stay at Calypso, Rebecca! We can't wait to have you back! :)
Verified

10/10 Excellent

Carole C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

short mama

great time . just one small suggestion, I am four foot ten, kitchen cabinets very high. a small step stool in pantry would be great
Stayed 7 nights in Jul 2021
Response from VrboOwner on 8 July 2023
Carole, Thank you for the review. We are glad you had a great time! Hope to see you again. Best Lynn
Verified

8/10 Good

Hui L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean spacious house with very limited consumable supplies

The house is clean and spacious with beautiful views and fair equipment. All the commumable supplies we got is 3 rolls of toilet paper and 1 roll of kitchen paper towel, one hand wash soap in 1
Stayed 3 nights in Dec 2020
Response from VrboOwner on 8 July 2023
Hi there! We are happy to hear y'all had a great time! :) Hope to have you again! Best, Lea Anna ~ Seaside Vacations
Verified

8/10 Good

Mauricio S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful Location

This is the perfect getaway if you want peace and quiet. Far from the hustle and bustle a city life brings. Great home to spend time with family and friends. Don’t plan on doing remote work from here as internet connection is extremely slow. Cellular connection is poor also. Clean and spacious. Just remember to bring your own pillows. Near the shore with beautiful views.
Stayed 6 nights in Apr 2021
Response from VrboOwner on 8 July 2023
Hi there! We are happy you enjoyed your stay at Calypso. :) We hope to have you back again! Best, Lea Anna
Verified

8/10 Good

Krista T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house with minor flaws

A group of friends and I stayed here for a week. Very clean house with lots of space for our large group. The balconies were very nice and it was a beautiful location. It was about a 30 minute drive to Chincoteague. The kitchen was updated with a full pantry, newer stove, and a fridge that had a water purifier built in. Check-in was online which was very convenient, but they don't give you the code to the house until actual check-in time. The internet connection at the house was poor but we could still stream shows on a lower quality setting. The queen beds were very nice but the bunk beds were a little too wobbly for comfort. Overall it was a nice place with full amenities!
Stayed 6 nights in Jun 2021
Response from VrboOwner on 8 July 2023
Hi Krista! Thank you for staying with us at Calypso in Captain's Cove! :) I am glad you enjoyed your stay! Hope to have you again! Best, Lea Anna ~ Seaside Vacations
Verified

8/10 Good

Lindsay F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chincoteague Stay

Overall we had a nice week. There were a few hiccups along the way with the amenity fees and then access. The HOA was not easy to work with per the management company, and this made it difficult when planning. Also, we had completed the form for our passes and it was received but then we were told it wasn’t received. So we weren’t able to use the amenities until our 4th day of vacation, but still were charged for the entire 8 days for the passes. The amenity pass is required even to use the playground and basketball court, which was a surprise to all parties. The washing machine had mold in it and there were no cleaning supplies for me to be able to clean it properly and the air vents were disgusting. I wouldn’t mention this except there is a cleaning fee attached to this property and I feel these items should be taken care of. When I brought them up, the property management team did say they would enter a work order. Also, we did not opt for the linen package, but didn’t think of pot holders as linens. So we were forced to purchase a set while on vacation. No big deal, just helpful to know for the next group. Ultimately, we would not stay here again, but would book with Seaside Vacations, they were easy to work with.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Mary Ann F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful

The home was beautiful and the location was great, very peaceful and serene. We had a couple bumps in the road that were addressed- the property manager was responsive however one issue was not resolved to my liking but it would not effect my rating of this property. I would definitely come to this area again.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Nancy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Serene and comfy

Everything was exactly as pictured. We especially enjoyed sitting on the high deck with our morning coffee. So quiet and comfy. Just the sound of the birds and views of the bay. We had everything we needed. (Except a griddle!) Such a nice vacation. Thank you!
Stayed 7 nights in Jun 2021
Response from VrboOwner on 8 July 2023
Nancy, Thank you for the review. We are happy you enjoyed your stay. Please visit us again. Best, Lynn
Verified

10/10 Excellent

Lisa F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and relaxing

Beautiful place. Enjoyed our stay.
Stayed 4 nights in May 2021
Response from VrboOwner on 8 July 2023
Hi Lisa! Thank you for staying with us! We hope to have you again! Best, Lea Anna ~ Seaside Vacations
Verified

10/10 Excellent

Sanford R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very peaceful, beautiful atmosphere, ample room, we loved it

This was a beautiful property, we really enjoyed ourselves. Group of 10 people slept comfortably in all the bedrooms. Felt like home away from home. Love the surroundings, love the home, we will visit again
Stayed 3 nights in May 2021
Response from VrboOwner on 8 July 2023
Hi there! Thank you for staying with us at Calypso in Captain's Cove! We hope to have you again soon! :) Best, Lea Anna ~ Seaside Vacations
Verified

10/10 Excellent

Tammy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely beautiful home. The view was amazing. Would definitely return.

Everything was easy, from sign up to rent to the check in and check out process. We couldn't have asked for a better place. The steps gave us our cardio for the week 😆
Stayed 3 nights in May 2021
Response from VrboOwner on 8 July 2023
Hi Tammy! We are happy to hear you enjoyed your stay at Calypso! Yes those steps are a work out! :) We hope to have you back again! Best, Lea Anna
Verified

8/10 Good

K S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice house

This house is perfect for two families to share. The Marina at Capitain Cove is literally 2 minutes drive away and their food is amazing. The house is about 30 minutes from Chincoteague, which we don’t mind. I do echo one of the earlier reviews about the internet. It is indeed dial-up slow and AT&T does not have good coverage. That did not matter to us because we wanted to be disconnected and the house offered a good selection of DVDs. The kitchen cookware can be expanded. Overall we enjoyed our stay.
Stayed 3 nights in Apr 2021
Response from VrboOwner on 8 July 2023
K S, So happy the house and location worked out for you. Disconnecting is a great way to unwind! We appreciate the comments regarding the kitchen supplies and internet. This feedback is exactly what we want. Come back soon. Best, Lynn
Verified

8/10 Good

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful Location

Nice quiet location. Everything was clean and comfortable. Set up for two families with kids. Internet was dial-up slow.
Stayed 16 nights in Feb 2021
Response from VrboOwner on 8 July 2023
Mark, Happy the house was set up for your needs. Internet is constantly being improved in this area. We are working on it. Visit soon. Best, Lynn

About the host

Hosted by Seaside Vacations & Sales

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

Go further with the Stayz app

  • Easily message your host
  • Access, share and manage your trip
  • Earn OneKeyCash on holiday rentals
Scan the QR code with your device camera and download our app
QR code to download the app