Greencastle Vacation Rentals from $191: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Greencastle has to offer?

Stunning Private Beachfront Estate on Beach : This highly rated vacation home rental in Greencastle is located by the ocean and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Greencastle is Your private get away hidden in historic island settlements .

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Vacation Rentals in Greencastle

Vacation Home in Rock Sound

Amy C.

Vacation Home in Rock Sound

Villa in Greencastle

Vacation Home in Greencastle

Vacation Home in Tarpum Bay

Paul D.

On the beach, sun loungers, beach towels

Vacation Home in Tarpum Bay

Anonymous traveler

Vacation Home in Tarpum Bay

"Our 4 night stay was okay but could have been much better with a bit more attention to both the house itself and to the communication.Upon arrival, the power was out. We’re familiar with power outages on island but without WiFi and sketchy cell service in the area, we had to drive 20 minutes down the road to inquire about the outage. We learned from the host- we never did get a response from the property manager- that there was a scheduled power outage that day and power would be back on in a...

sue r.

Villa in Governors Harbour

"This property is absolutely beautiful. It is set up perfectly for large groups. The location is gorgeous and you could spend the entire time exploring just this property! The house manager is wonderful and overall it was a great experience. I would only change two things: the mattresses could use a change and I would have loved to have some black out curtains- but I’m not a morning person so if you don’t mind bright sunshine in your room at 6:30am you’ll be fine!"

Lisa W.

Villa in Windermere

Stacey F.

Cottage in Rock Sound

Eustacia

Vacation Home in Windermere

Brett A.

Vacation Home in Governors Harbour

Sarah L.

Cottage in Savanah Sound

Vacation Home in Tarpum Bay, Eleuthera , Bahamas

Charlotte F.

Villa in Savannah Sound

Robert V.

Apartment in Rock Sound

Vacation Home in Windermere

Tiffany C.

Apartment in Tarpum Bay

IAN S.

$179 nightly

Nov 30 - Dec 1

Total with taxes and fees

Vacation Home in Rock Sound

Atalanta v.

Vacation Home in Windermere Island

"If you are looking for a getaway that has the luxury of watching your favorite show while enjoying the solitude and serenity of being isolated from the daily grind, you've found the right place. The solitude is intoxicating watching the sun go down whether it be from the dock or poolside. The reset it wonderful, relaxing and surprisingly more than you'd expect. I got engaged while visiting this location and it's a memory that my closest friends and I will never forget!!"

Sam O.

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Top Greencastle Hotel Reviews

Private family beach bungalow - on a beautiful swimming beach

10/10 Excellent

"Awesome trip, fantastic property. Very comfortable, highly recommended. It’s a perfect spot. "

ULTRA LUX Coconut Cove Compound! 2.5 acres with 300 ft PINK SAND BEACH

10/10 Excellent

"We have stayed in Winding Bay several times many years ago. This is a relatively new home that includes a 4 bedroom guest house so a great amount of space for all ages. Kitchen was well equipped, bedrooms were spacious and comfortable, and all the living areas perfect for those late afternoons before dinner. Outside space is incredible with a huge deck, picnic tables, lounges, chairs, covered area, kayaks, paddle boards, water trampoline, and water toys. There is a large bar/grill area with outdoor tv as well. We rented the large Suburban which the owner had left for us at the airport and was perfect for 7 of us and all our luggage. Winding Bay is the perfect spot if you want to spear lobster and/or fish as it is on the ocean side but protected from the Atlantic. We had lobster ever. single. night. Please note the season opens there on August 1st. This home was just great for our family with ages 6 - 75. The host, Chris, is outstanding and will communicate immediately if asked a question or have a concern. We would do a repeat visit to this compound. As our six year old said, "let's go home for two days and then come back." I agree. Thank you, Chris. It was a terrific vacation."

Private Home With Ocean Views, Short Walk to Beach & Club w/Pool, Tennis, Gym

10/10 Excellent

"We enjoyed our stay at Sundowner Villa. The house was clean and very well appointed. The host’s description was accurate, we only needed the air conditioning on very calm days. We enjoyed using the kayaks on Savannah Sound. There are several bonefish flats adjacent to the island, and the Bonefishing was good. Local restaurants and a grocery store made our stay very comfortable. We hope the hosts will let us rent their VRBO again. We definitely will return."

House of Love - Perfect Vacation Spot

6/10 Okay

"Our 4 night stay was okay but could have been much better with a bit more attention to both the house itself and to the communication.Upon arrival, the power was out. We’re familiar with power outages on island but without WiFi and sketchy cell service in the area, we had to drive 20 minutes down the road to inquire about the outage. We learned from the host- we never did get a response from the property manager- that there was a scheduled power outage that day and power would be back on in a few hours. Would have been good to know this before we arrived.The dishwasher was not working, there was a sign posted for this. The temp in the refrigerator was only ‘freezing’. The was broken as well and we couldn’t adjust it. Learned that overnight when we found frozen milk, fruit, juice, etc the next morning. We started our first day by throwing out about 30 worth of frozen food that should not have been frozen.On the bedroom windows, there are no curtains, only shears, providing no room darkening/ privacy, especially from the vehicle lights on the main highway.There were very limited bath towels and washcloths,which we could have resolved but there was no laundry soap.The AC worked well, the house was spacious and the view was as pictured . This house is right on the main road so traffic could be noisy at times.A few more bath towels, a better working fridge and a bit more communication would have made this a better stay.For the price, there should have been more value."

Find out more about Greencastle

Everything you need to know about Greencastle vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greencastle vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greencastle vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greencastle vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greencastle. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greencastle in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $191 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greencastle rentals

At Expedia, we put the best Greencastle vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greencastle rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greencastle vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greencastle. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Greencastle?

Yes, we offer vacation rentals close to the most popular points of interest in Greencastle, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Greencastle has to offer?

Stunning Private Beachfront Estate on Beach: This highly rated vacation home rental in Greencastle is located by the ocean and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Greencastle is Your private get away hidden in historic island settlements.

How many vacation rentals are there in Greencastle?

Expedia has 4 vacation rentals for your stay in Greencastle.

What’s there to see and do in Greencastle?

While you're exploring the area, Cotton Bay and Cape Eleuthera are a couple of picturesque spots to get outside and enjoy nature. Cotton Bay Club Golf Course and Ocean Hole are a couple of places you'll find in the larger area.

What’s a vacation rental in Greencastle like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Greencastle. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

Greencastle Vacation Rentals

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Vacation Rentals in Greencastle

Vacation Home in Rock Sound

Vacation Home in Rock Sound

Villa in Greencastle

Vacation Home in Greencastle

Vacation Home in Tarpum Bay

Vacation Home in Tarpum Bay

Vacation Home in Tarpum Bay

Villa in Governors Harbour

Villa in Windermere

Cottage in Rock Sound

Vacation Home in Windermere

Vacation Home in Governors Harbour

Cottage in Savanah Sound

Vacation Home in Tarpum Bay, Eleuthera , Bahamas

Villa in Savannah Sound

Apartment in Rock Sound

Vacation Home in Windermere

Apartment in Tarpum Bay

Vacation Home in Rock Sound

Vacation Home in Windermere Island

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Top Greencastle Hotel Reviews

Private family beach bungalow - on a beautiful swimming beach

Find out more about Greencastle

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