Discover a selection of 16 vacation rentals in Greencastle, BS that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including kitchens and dishwashers. Prices start at $110 per night, and houses and cottages are popular options for a stay in Greencastle. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Greencastle
Destination guide

Find the perfect vacation rental for your Greencastle getaway

Experience the unique character of Greencastle with a stay in a vacation home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Natural features

Exploring the natural features in Greencastle

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Greencastle is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Winding Bay (12.7 mi / 20.4 km)
  • Ocean Hole (7.1 mi / 11.4 km)
  • Cape Eleuthera (9.2 mi / 14.8 km)
  • Lighthouse Beach (11.7 mi / 18.9 km)
How to get there

Transportation options to and around Greencastle

The nearest airport is in Rock Sound (RSD-Rock Sound Intl.), located 8.5 mi (13.7 km) from the city center.

What are the top vacation rentals in or near Greencastle?

Whether you're looking for a cozy escape for you and your boo or a sprawling house to fit all your friends, you'll find some top vacation rentals in and around Greencastle. Here are a couple to start you off:

  • Around 2 miles from the center of Greencastle, you'll find it hard to resist "Oceanfront Perfection - Daily Housekeeping". It has 5 bedrooms and a range of amenities including cookware, dishware and utensils and cable/satellite TV services.
  • Alternatively, make your home away from home at "Tara Estates Tucked Away On A Private Property". Located around 10 miles from the heart of Greencastle, it has 3 bedrooms and comes with a fridge and cookware, dishware and utensils.

For even more great options, use the search bar at the top of the page to find the perfect Greencastle vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Greencastle?

Nothing beats a quick break to recharge your batteries. Pack your overnight bag and take five at one of these appealing weekend getaways in and around Greencastle:

  • Located 10 miles to the north of the center of Greencastle, "The Pilot House, "inn Between The Beaches" #2" is a favorite with nature buffs and adventurous types. Find your way to nearby outdoor attractions, including Ocean Hole and Cotton Bay Club Golf Course. If you're up for some fun activities, try snorkeling or fishing.
  • Alternatively, find your home away from home at "The Pilot House, "inn Between The Beaches" #4". Use it as a base to relax, or be adventurous and try snorkeling and fishing. When it's time to discover more of the area, plan a visit to Lighthouse Beach and Cape Eleuthera. This attractive vacation rental is around 10 miles north of Greencastle.

Can I find studio apartments for rent in and around Greencastle?

Studio apartments may be small in size, but they pack a punch when it comes to location and convenience. Plonk your bags down at one of these top studio apartments in and around Greencastle:

  • After a day filled with outdoor exploration, relax in total comfort at "The Pilot House, "inn Between The Beaches" #2". Internet services and nearby ecotour services are just some of the amenities you'll find here.
  • Alternatively, use "The Pilot House, "inn Between The Beaches" #4" as a base to check off the sights around you. This cozy home away from home comes with a smart TV, free WiFi and more.

Can I find short term rentals in or near Greencastle?

Yes, you certainly can! Vrbo's short-term rentals in Greencastle provide a great alternative to your typical hotel stay. Offering many of the comforts and conveniences of home, you'll effortlessly switch into vacation mode the minute you arrive. Try these fantastic rentals on for size:

  • Stay a few nights at "High Tide Villa - Winding Bay, Eleuthera" in central Greencastle. Here, you'll have easy access to popular attractions like Cotton Bay Club Golf Course.
  • Or maybe "Oceanfront Luxury Private Home" is a better match. Check out nearby sights like Powel Point Marina during the day and then relax in your comfy digs at night.

What are the best romantic weekend getaways in or near Greencastle?

Forget about roses and chocolates. Sometimes all you need is to take off for a weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Greencastle that would make even old Cupid green with envy. Here are some we think you'll fall in love with:

  • Slip away on Friday afternoon for a few passion-filled evenings at "Oceanfront Perfection - Daily Housekeeping". Approximately 2 miles from Greencastle, it comes with plenty of nice touches, including a fireplace and air conditioning.
  • Another place where you can enjoy a few precious days together is "Tara Estates Tucked Away On A Private Property". Located around 10 miles from Greencastle, massage services and a fireplace add to the atmosphere here.

What are the best large family vacation rentals in or near Greencastle?

You love your family, but that doesn't mean you need to squash together like sardines during your vacation. Take no chances and go for a large family vacation rental in or around Greencastle where you can spread out and relax:

  • Suitable for up to 10 guests spread out over 5 bedrooms, "Oceanfront Perfection - Daily Housekeeping" is always popular with big families. It comes with a kitchen and a barbecue grill and is located around 2 miles east of Greencastle.
  • Another awesome option is "High Tide Villa - Winding Bay, Eleuthera". It's approximately 12 miles to the north of Greencastle, has 3 bedrooms and accommodates up to 10 guests. Nearby ecotour services and a dining table are among the many conveniences on offer here.

Are there vacation rentals with fire pits in or near Greencastle?

Whether you're eager to share a bottle of vino beside the flames with your beau or just stay nice and warm once the sun goes down, we'll help you find a vacation rental with a fire pit. Here are two of our favorite options in or near Greencastle:

  • Cuddle up with your nearest and dearest around a crackling open fire at "Private Beachfront Family Vacation Home". A garden and a nearby waterfront are other handy amenities you'll find here.
  • Light up a blaze and then savor the tranquil vibe at "Experience Real Eleuthera: Stay In A Sleepy Fishing Village On The Sea". This sought-after escape also comes with a beach view and a firepit.