Calypso vacation rentals

We found vacation rentals — enter your dates for availability

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Calypso

Find out more about Calypso

Why visit Calypso

  1. Beautiful Beaches: Calypso features stunning coastlines perfect for relaxation and sunbathing.
  2. Amusement Parks: Nearby attractions provide thrilling rides and family-friendly activities for all ages.
  3. Charming Accommodations: Choose from luxurious oceanfront condos and spacious vacation homes with breathtaking views.
  4. Scenic Strolls: Enjoy leisurely walks along the esplanade, taking in the vibrant atmosphere and ocean views.
  5. Outdoor Adventures: Engage in various outdoor activities, from water sports to nature exploration, ensuring an active getaway.

Popular types of accommodation around Calypso

Planning a getaway to Calypso? The next exciting step is selecting your perfect accommodation. Explore our top choices for vacation rentals, which include stunning oceanfront condos, spacious houses, and inviting apartments. Enjoy breathtaking views from an oceanfront balcony or unwind in a cozy bedroom oceanfront condo. Experience the best of Calypso with transparent pricing and reassurance, making your stay unforgettable.

  • Condos: The top choice for vacation rentals in Calypso, offering modern amenities and convenient locations for an enjoyable stay.
  • Houses: A popular option for families and groups seeking spacious and comfortable accommodations for their getaway.
  • Apartments: A well-liked alternative that provides a home-like atmosphere, perfect for a shorter stay in Calypso.
  • Cottages: Charming and cozy, these rentals are ideal for those wanting a quaint experience close to nature.
  • Villas: The fifth most popular choice, offering luxurious spaces for a relaxing retreat in Calypso.**

Top attractions around Calypso

Calypso, Ocean City, Maryland, offers a delightful mix of attractions for a memorable vacation. Visitors can enjoy the beautiful beaches, stroll along the esplanade, and experience the thrills of nearby amusement parks. Whether you're seeking outdoor adventures or family-friendly activities, Calypso provides plenty of options to create lasting memories during your stay.

  1. Ocean City Boardwalk: A lively 6.4km esplanade perfect for family outings or romantic strolls. Enjoy vibrant shops, delicious eateries, and street performances while soaking in the outdoor atmosphere.
  2. Ocean City Beach: A stunning beach located 6.4km away, offering soft sand and refreshing waves. Ideal for sunbathing, beach games, and relaxing by the ocean.
  3. Jolly Roger Amusement Park: Just 3.2km from Calypso, this amusement park features thrilling rides and attractions, making it a fantastic destination for adventure-seeking families.

Things to do recommended for couples

For a charming getaway near Calypso, enjoy a fun round at Maui Golf, only 483m away. For a thrilling adventure, visit Shark's Cove Marina, 8.0km distant. Finally, indulge in romance at Costa Ventosa Vineyard and Winery, located 17.7km away, perfect for a cozy evening together.

Things to do recommended for families

Your family vacation in Ocean City, Maryland, will be filled with fun! Enjoy ice skating at Carousel Ice Skating Rink, relax at Northside Park, and splash around at Frontier Town Water Park and Golf. Each destination offers unique experiences for unforgettable family adventures.

Things to do recommended for groups

Groups visiting Calypso can enjoy a fun-filled day at Seacrets Distilling Company for some local brews, try their luck at the Casino at Ocean Downs, or shop for unique finds at Gold Coast Mall, each offering a lively atmosphere perfect for making memories together.

What do I need to keep in mind when booking a vacation around Calypso

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritise your preferences when filtering options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Calypso with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Calypso with young kids: Travelling with young children can present some challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Calypso: For many families, a trip isn’t truly whole without their furry companion. If that resonates with you, consider exploring Vrbo properties that are pet-friendly. Most accommodations that welcome pets offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Calypso: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay around Calypso

Your vacation in Calypso, Ocean City, Maryland, promises an unforgettable experience filled with relaxation and family-friendly activities. Discover the scenic beauty of Ocean View and unwind in a charming vacation condo. With its trendy atmosphere and stunning coastlines, Ocean City is the ultimate destination for creating lasting memories. Enjoy the perfect blend of vibrant beach life and peaceful retreats, making your trip to Calypso a true escape.

  • Midtown Ocean City: Midtown Ocean City is a vibrant neighbourhood located a mere 483m from Calypso. This area is perfect for outdoor enthusiasts, couples seeking a romantic getaway, and families looking to create lasting memories. The iconic boardwalk is within easy reach, offering a delightful mix of shops, eateries, and entertainment options. Families can enjoy the nearby water park and the inviting family beach, making it an ideal spot for a fun-filled day by the ocean. The esplanade also provides a scenic pathway for leisurely strolls, ensuring a memorable travel experience.
  • Sunset Island: Situated 805m from Calypso, Sunset Island is a picturesque neighbourhood known for its beautiful beaches and outdoor activities. Perfect for those seeking romance or a relaxing beach experience, Sunset Island offers easy access to the boardwalk and a lovely golf course for avid players. Visitors can bask in the sun at the family beach or take a leisurely walk along the esplanade. With stunning sunset views and tranquil surroundings, this charming area is a must-visit for anyone looking to unwind and enjoy the coastal beauty of Ocean City.
  • Little Salisbury: Located 1.6km from Calypso, Little Salisbury is a delightful neighbourhood that offers an inviting blend of beach experiences and outdoor adventures. This area is perfect for couples and families alike, with plenty of opportunities for shopping, recreation, and enjoying the beautiful beach. The local boardwalk provides a lively atmosphere with various attractions, while the family beach and esplanade create the perfect setting for a relaxing day by the sea. Little Salisbury promises a fulfilling travel experience with its friendly vibe and scenic surroundings.

Best time to go to Calypso

If you're planning a trip to Calypso, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.8°F (3.8°C)Light RainMostly SunnyLowSlightly Low
February40.5°F (4.7°C)Light RainMostly SunnyLowSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
May63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
June72.0°F (22.2°C)Light RainMostly SunnyHighSlightly High
July77.7°F (25.4°C)Light RainMostly SunnyHighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyHighSlightly High
September72.0°F (22.2°C)Light RainMostly SunnyAverageAverage
October63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
November52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
December45.0°F (7.2°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new journeys, pick up right where you left off, or manage and arrange your travel plans. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

More Vacation Rentals ideas

People also search for