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Five O'Clock on the Hill
Average rating:  
 7 reviews
 by Dana Heuschkel
Hurricane victims pampered
Date of Stay: 9/13-9/15/17
Source: Mile Marker & amazing rescue crew

Roy Chilson took me & my fella Tadis in amongst many other evacuees from St. John after Hurricane Irma reduced our beautiful island home to rubble. Roy always had the coffee on in the mornings, let us wash our mildewing clothes, gave us a gorgeous room with a King bed to rest our weary heads after a grueling 5 hour CHOPPY boat rescue into the dark night.

Roy gave us a safe place to recoop ourselves after all of our ordeal. We will forever remember his kindness & laughter. Tadis already has our vacation home picked for after we rebuild the life that was ripped from us. 5 O'clock on the Hill holds a special place in my heart.

The morning we woke to overlooking our bedroom window the crashing waves & to see our spectacular Caribbean Sea...I knew we would be ok. Bless all the wonderful people who took care of us from the dock & throughout our stay. The night at Castaways will never be forgotten. Roy & Tadis ...ooooh the belly rolling laughs we had!!! Stay at 5 O'clock on the Hill. Memories = Priceless!

 by Megan McLean
A Trip of A Lifetime
Date of Stay: 5/26-6/4

Roy was the perfect host! Not only did he meet us at the airport, but he even took us to the grocery store along the way to make sure we were all set for our week stay. He gave us all the best recommendations for all "touristy" activities as well as more local activities...our favorite local spot was Ziggys!!!

Upon arriving at his property, we were immediately taken away by the views. The five bedroom villa overlooked the ocean and was extremely private. While the rooms were cozy, we found ourselves wanting to spend more time outside to enjoy the amenities of the property. Floating in the pool, practicing yoga on the deck, hiking to the beach, relaxing in the lounge chairs and even having outdoor movie nights were some of the highlights of the trip!

Our trip was so enjoyable that we went home considering moving to the island! Thank you, Roy, for such a memorable trip 🙂

 by Nancy L.
Date of Stay: March 2017
Source: VRBO

For two weeks, four couples enjoyed privacy AND camaraderie – we each had our own BR and BA but the common area was perfect for shared dinners and game nights. We loved the access to the trailhead to Jack’s and Issac’s beaches and even hiked Goat Hill to view the glorious colors of the Caribbean on both sides of Point Udall. The pool was refreshing and we had unlimited seating areas. Having a vehicle provided the opportunity to explore all this laid- back island offers. While we enjoyed the fully equipped kitchen(s) and shared many meals “at home”, we also must recommend Blue Terrace Restaurant, Duggans, and Chenay Beach Bar on the East End. Sandy Point is an incredible beach open just on weekends. While on the West End, you will love the menu at Sand Castle, dinner at C I Bone, and Rhythms at Rainbow Beach for lunch. Of course, no trip is complete without visiting Christiansted. So many restaurants and bars, all delicious. A sail at sunset was a true highlight. The same crew took us all out to Buck Island where we loved the snorkeling and can attest to the beauty of Turtle Island. Lunch at Buccaneers, a visit to Shoy’s Beach, a visit to Frederiksted when the cruise ship was in, and an opportunity to watch the St. Patrick’s Day parade in Christiansted were all highlights. We’ve been home only a week and all of us cannot stop sharing stories and pictures of our wonderful visit. In closing, the most memorable part of our visit is the awesomeness of our host, Roy Chilson. We cannot say enough about this amazing man. He went far above and beyond to assure our vacation was as special as this villa. Thank you from all of us. We loved every minute of our St Croix vacation!

 by Shane C.
2nd Time Here!! Amazing once again!
Date of Stay: February 2017
Source: VRBO

As the title reads, we have been here twice within a six month period. First time we came with 11 people and it was perfect for everyone, including our 6 year old and 8 year old. Never once did they ask to watch TV! This trip was just for my wife and I. Perfect location for our Valentine’s getaway! I want to let you know that the breezes here are second to none. At no point did I feel like we needed AC in this house due to the perfect location and layout. Slept like a baby listening to the waves crashing below. And, once again, Roy was an amazing host. There is just something about this island and the people that just keep us coming back!

 by Inga R.
Celebrating 50 @ 5 O’Clock
Date of Stay: November 2016
Source: VRBO

For that Special milestone Birthday I wanted a place where my family could join me and celebrate ,The House was perfect the rooms are nice & private all with Oceanview I loved hearing the waves at night The outdoor dining was amazing for Breakfast & Dinners with a large group! And the private pool relaxing both Daytime And Nightswim when the pretty lights are on Would Stay @ 5 O’clock again for sure Inga

 by Cathleen S.
Best Christmas!!
Date of Stay: December 2016
Source: VRBO

My parents, three sisters and our families spend the holiday together, this year in St. Croix. Roy was the perfect host!! Because we flew in on Christmas Eve, he called around to ensure the grocery stores would be open and had someone meet us at the airport and wait while we gathered supplies. He also set up a Christmas tree so Santa could visit during our stay. He also helped arrange a trip to Buck Island and Christmas dinner reservations. His home is the perfect setting for a large group. Everyone had ample space and we loved all the beaches and hiking trails. The outdoor patio was a great place to eat family meals together, enjoy the fabulous views and play games in the evening. It was a beautiful, relaxing vacation and our Vice President even paid a visit while we were there!

 by Stacey S.
Beautiful location for a retreat
Date of Stay: November 2016
Source: VRBO

This private villa provided an excellent location for our Rejuvenation & Restoration Retreat. In their free time, participants were able to enjoy the ample space around the property and still feel like they had privacy. The villas close proximity to hiking trails & beaches provided the perfect opportunity to get outside and enjoy nature. In addition the porches were perfect for a yoga class under the stars and a sunrise yoga class. Roy was great to work with as we coordinated this event- he was very accommodating! I would definitely host another retreat here in the future!