--- title: "Skytop Vacation Packages 2026 from $1,260 | Expedia" description: "Bundle Skytop flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Skytop.d553248635976400500.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-14T08:39:33Z --- # Skytop Vacations from $1,260 ![A turquoise sea, a sandy beach, and lush green hills.](https://images.trvl-media.com/place/186/36d6880f-5b2c-4da6-a43e-b7385be7bf82.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## The Latest Skytop Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A resort with a large pool, multiple buildings, and a view of the ocean.](https://images.trvl-media.com/lodging/12000000/11800000/11796200/11796106/fce322aa.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A swimming pool with lounge chairs and umbrellas, a thatched-roof structure, and a sign for 'Chill Beach'.](https://images.trvl-media.com/lodging/12000000/11800000/11796200/11796106/d61b119f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 7 - Feb 12** ### [Margaritaville Vacation Club - St. Thomas + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-07/2027-02-12/?FromAirport=BOS&Destination=STT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11796106&dealMarker=&paandie=true&cabinClass=e) St. Thomas 5 nights **8.0/10** \- Very good (2,448 reviews) Roundtrip • Boston (BOS) - St. Thomas (STT) BOS - STT • Nonstop STT - BOS • Nonstop [~~$1,866~~](https://www.expedia.com/) **$1,260** per traveler found 1 day ago - ![A coastal landscape with a beach, clear blue waters, and lush greenery.](https://images.trvl-media.com/lodging/120000000/119840000/119839900/119839838/c142bc73.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A round wooden dining table set for six with wicker chairs, a vase of yellow flowers, and a hanging light fixture.](https://images.trvl-media.com/lodging/120000000/119840000/119839900/119839838/12cc8693.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 7 - Feb 12** ### [Villa Island Paradise + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-07/2027-02-12/?FromAirport=BOS&Destination=STT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=119839838&dealMarker=&paandie=true&cabinClass=e) St. John 5 nights **9.6/10** \- Exceptional (42 reviews) "St. Thomas is prone to blackouts. During our stay we experienced one which left us without AC in a very hot destination. This villa does not have a back up generator for when the power goes out. Outside of that this place was great and the owners were responsive when we contacted them. All other amenities were taken care of even beach chairs, cooler, beach umbrella, and some snorkeling gear!" Reviewed November 13, 2026 Roundtrip • Boston (BOS) - St. Thomas (STT) BOS - STT • Nonstop STT - BOS • Nonstop [~~$3,875~~](https://www.expedia.com/) **$2,403** per traveler found 1 day ago - ![A beach with clear turquoise water, a sandy shore, and a lush green hill in the background.](https://images.trvl-media.com/lodging/1000000/530000/527900/527815/beab7878.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A spacious living area with a high ceiling, large windows, and a view of palm trees.](https://images.trvl-media.com/lodging/1000000/530000/527900/527815/6e35310c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 7 - Feb 12** ### [Limetree Beach Resort by Club Wyndham + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-07/2027-02-12/?FromAirport=BOS&Destination=STT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527815&dealMarker=&paandie=true&cabinClass=e) St. Thomas 5 nights **8.2/10** \- Very good (250 reviews) "The studio was clean, the staff was always available when needed, the swim-up bar fabulous and the bar was excellent and the alcohol drinks outstanding." Reviewed October 30, 2026 Roundtrip • Boston (BOS) - St. Thomas (STT) BOS - STT • Nonstop STT - BOS • Nonstop [~~$2,318~~](https://www.expedia.com/) **$1,569** per traveler found 1 day ago - ![View from property](https://images.trvl-media.com/lodging/12000000/11980000/11973000/11972959/23f2c87a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11980000/11973000/11972959/8539dd31.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 7 - Feb 12** ### [Sea Shore Allure + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-07/2027-02-12/?FromAirport=BOS&Destination=STT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11972959&dealMarker=&paandie=true&cabinClass=e) St. John 5 nights **10/10** \- Exceptional (48 reviews) "The property was very clean and well kept. Our room was very clean and they had everything you could need in the kitchen. The views were amazing and it’s very close to several restaurants nearby! The pool area was also amazing and they had beach chairs and coolers we could take to the beach. Highly recommend!" Reviewed November 13, 2026 Roundtrip • Boston (BOS) - St. Thomas (STT) BOS - STT • Nonstop STT - BOS • Nonstop [~~$5,245~~](https://www.expedia.com/) **$3,722** per traveler found 1 day ago - ![A beach with clear water, palm trees, and sun loungers.](https://images.trvl-media.com/lodging/1000000/530000/527900/527816/41f1ab0e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A clear tropical beach with palm trees and a starfish visible in the shallow water.](https://images.trvl-media.com/lodging/1000000/530000/527900/527816/202eca37.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 24 - Dec 29** ### [Club Wyndham Elysian Beach Resort + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-24/2026-12-29/?FromAirport=BOS&Destination=STT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527816&dealMarker=&paandie=true&cabinClass=e) St. Thomas 5 nights **8.0/10** \- Very good (209 reviews) "We had to request towels several times." Reviewed November 13, 2026 Roundtrip • Boston (BOS) - St. Thomas (STT) BOS - STT • Nonstop STT - BOS • 1 stop [~~$2,831~~](https://www.expedia.com/) **$2,012** per traveler found 1 day ago ## Where to stay in Skytop Find the best Skytop areas and neighborhoods for the activities you enjoy most. - [Maho Bay Quarter](#) - [Contant Farms](#) - [Upper Carolina](#) - [Rendezvous & Ditleff](#) - [Lower Carolina](#) ![A beach with turquoise water, people swimming, and a mountain in the background.](https://images.trvl-media.com/place/6068171/2dcfaa55-6fa6-46f5-a195-440beabd041d.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Maho Bay Quarter](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635975749486) ### Maho Bay Quarter If you're spending some time in Maho Bay Quarter, Maho Beach and Cinnamon Bay Beach are top sights worth seeing. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635975749486) ![A coastal town with a marina, lush greenery, and a sunset over the ocean.](https://images.trvl-media.com/place/553248635976399752/d5f46338-b1f8-4162-8c73-a41a854fb932.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Contant Farms](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635976399752) ### Contant Farms If you're spending some time in Contant Farms, Great Cruz Bay and Turner Bay are top sights worth seeing. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635976399752) ![A pool overlooking a bay with boats and a hilly landscape.](https://images.trvl-media.com/place/11644/83adf16a-528f-4e6c-bad5-7861dbeb2bde.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Eric Sturgeon [View properties in map for Upper Carolina](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635976913042) ### Upper Carolina While visiting Upper Carolina, you might make a stop by sights like Virgin Islands National Park and Ajax Peak. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635976913042) ![A coastal town with a marina, lush greenery, and a sunset over the ocean.](https://images.trvl-media.com/place/553248635976399752/d5f46338-b1f8-4162-8c73-a41a854fb932.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Rendezvous & Ditleff](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635976398063) ### Rendezvous & Ditleff While visiting Rendezvous & Ditleff, you might make a stop by sights like Rendezvous Bay and Klein Bay. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635976398063) ![A turquoise sea, a white sandy beach, and lush green hills.](https://images.trvl-media.com/place/553248635976384333/f1f913c9-eef9-4cbd-8e24-277da961fefd.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Lower Carolina](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635976384333) ### Lower Carolina If you're looking for some top things to see and do in Lower Carolina and surrounding area, you can visit Virgin Islands National Park and Maho Beach. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635976384333) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.