Beginning of main content
Leeward Islands
Vacation Travel Guide
Top Hotels Close to Leeward Islands
Brimstone View Guest Apartments
Main Rd, New Guinea, Old Road Town
Situated in a national park, this guesthouse is 0.3 mi (0.4 km) from Brimstone Hill Fortress National Park and 3 mi (4.9 km) from Romney Manor. Mount Liamuiga ...
Statia Lodge
White Wall, Oranjestad, Sint Eustatius
Situated in a rural location, this lodge is within 3 mi (5 km) of St. Eustatius Historical Foundation Museum, Honem Dalim Synagogue Ruins, and Fort Oranje. Lower ...
The Old Gin House
Oranjebaai 1, Oranjestad, Sint Eustatius
Fully refundable
Nestled on the beach, this Oranjestad hotel is within a 5-minute walk of Lower Town Beach and Fort Oranje. Honem Dalim Synagogue Ruins and St. Eustatius Historical ...
4.2/5 Very Good! (18 reviews)
"Saybolt and Merlies are an extremely attentive in all the senses possible. Whatever you may ask they going to make it possible even in this C-19 situation. Rooms are right next to the sea. Food is above the standards with some dishes really amazing. If you want to recharge your batteries give a chance ..."
Reviewed on May 19, 2021
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Plan a trip to see Leeward Islands
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Price was $1,341, price is now $998 per person
$998
per person
Jan 15 - Jan 20
Roundtrip non-stop flight included
Houston (IAH) to Montego Bay (MBJ)
4.1/5 Very Good! (1,001 reviews)
Property was nice. Staff was constantly working on the grounds. Cleaning could’ve been better. On arrival to our room windows and pieces of furniture had not been cleaned. It’s also possible no one had stayed in the room in some time and a refresher had not been done. I like there were many restrooms around the resort and they were always clean.
Reviewed on Nov 24, 2021
Ocho Rios Villa at Coolshade III
Price was $969, price is now $728 per person
$728
per person
Dec 29 - Dec 31
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
4.5/5 Wonderful! (8 reviews)
Lovely property, very quite and tranquil community. If not for the kids I would have spent the afternoons curled up on the veranda reading a book. The staff was very attentive. The price was a very good deal for the amenities.
Reviewed on Jul 23, 2019
Don't see what you're looking for?
See all available trips from Ashburn to Leeward Islands
View all tripsRead travel guides and advice on visiting Leeward Islands
Pirate Vacation, Ahoy! 7 Swashbuckling Destinations in the US & Caribbean
Exploring Excellence Oyster Bay, Jamaica: The Excellence Collection’s Newest Adults-Only All-Inclusive Resort
Popular places to visit in Leeward Islands
Sapphire Beach
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
Trunk Bay
Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.
Flamenco Beach
Nothing says vacation like spending a lazy day at Flamenco Beach, a popular beach in Culebra. Stroll along the seaside or seek out the snorkeling spots.
Magens Bay Beach
Appreciate the excellent views of hilly forests as you meander along a scenic trail on your way to this haven of white sand and inviting water.
Virgin Islands National Park
Hike on scenic trails, explore sugar plantation ruins and snorkel along an underwater trail in this pristine nature park, which covers much of St. John.
Coki Point Beach
Ample facilities and warm hospitality combine to make this one of the most appealing beaches on the island.
Leeward Islands
Best Lodging Options Near Leeward Islands
Check prices on hotels close to Leeward Islands
Brimstone View Guest Apartments
Main Rd, New Guinea, Old Road Town
Statia Lodge
White Wall, Oranjestad, Sint Eustatius
The Old Gin House
Oranjebaai 1, Oranjestad, Sint Eustatius
Orange Bay Hotel
Oranjebaaiweg 21, Lower Bay, Oranjestad
Talk of the Town
Oranjebaaiweg 1 Lowertown, Oranjestad, St. Eustatius
Belle Mont Farm
The Village Kittitian Hill St. Kitts, Saint Pauls, St. Kitts
Golden Rock Dive And Nature Resort
Behind the mountain #21, Sint Eustatius Bonaire, Oranjestad
K'O- Rooms B&B
Carl Nicholson Road #13, Oranjestad, Sint Eustatius
Belle Mont Farm
The Village Kittitian Hill, Saint Pauls, Saint Paul Capisterre Parish
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
- Plan your trip to Leeward Islands
- Popular Vacation Destinations
- More Hotel Options in Leeward Islands
- Other Hotels near Leeward Islands, Caribbean
- Hotels near popular Attractions
- Expedia's Latest Trends
- Walt Disney World Packages
- Universal Studios Hollywood Vacations
- Redwood National and State Parks Vacations
- Breckenridge Ski Resort Vacations
- Navy Pier, San Diego Vacations
- Legoland California Vacations
- Trunk Bay Vacations
- Great Smoky Mountains National Park Vacations
- SeaWorld® Orlando Vacations
- Alcatraz Island Vacations
- Broadway Vacations
- Creation Museum Vacations
- Grand Teton National Park Vacations
- Dry Tortugas National Park Vacations
- Busch Gardens Tampa Bay Vacations
- Space Needle Vacations
- Six Flags Over Texas Vacations
- Pikes Peak Vacations
- SeaWorld Vacations
- AT&T Stadium Vacations
Hotels
Hotel Rooms in Snug CornerResorts & Hotels with Spas in San Pedro de MacorisGrande Riviere Resorts & Hotels with SpasAntigua Hotels with Free Airport ShuttleCrown Point Hotels with a PoolAll-inclusive Resorts in TrelawnyAntigua Hotels with Free BreakfastAntigua 3 Star Star HotelsEast End Hotel Wedding VenuesLong Bay Beach hotelsCasinos in San Pedro de MacorisCrown Point All-inclusive ResortsProvidenciales Luxury HotelsEast End 5 Star Star HotelsHoneymoon Resorts & Hotels in Saint JohnProvidenciales Adults Only Resorts & HotelsBeach Hotels in Saint John
Activities
Vacation Rentals
e7c874d2-33f8-47cd-9f84-bcf4529dcb9ea8c8189a-5656-47a5-afde-c06aae6776d200000000-0000-0000-66a0-190325150b02