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Windward Islands Vacation Packages

Windward Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Banana Bay Resort & Marina

Banana Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Nov 18 - Nov 22
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3-star golf hotel in Marathon. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the bar in our reviews. Popular attractions Sombrero Beach and Florida Keys Country Club are located nearby.
Sheraton Rome Parco de’ Medici

Sheraton Rome Parco de’ Medici

4 out of 5
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Stay at this 4-star golf hotel in Rome. Enjoy 2 outdoor pools, 3 restaurants, and a golf course. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Palazzo dello Sport and Circus Maximus are located nearby.
Cardo Roma, Autograph Hotel

Cardo Roma, Autograph Hotel

4 out of 5
per person
Nov 18 - Nov 22
found 5 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Stay at this 4-star business-friendly hotel in Rome. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Colosseum and Roman Forum are located nearby.
Hotel Smeraldo

Hotel Smeraldo

3 out of 5
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Stay at this 3-star hotel in Rome. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the bar in our reviews. Popular attractions Campo de' Fiori and Pantheon are located nearby.
Courtyard by Marriott Rome Central Park

Courtyard by Marriott Rome Central Park

4 out of 5
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Stay at this 4-star family-friendly hotel in Rome. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Vatican Museums and Sistine Chapel are located nearby.
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
per person
Nov 7 - Nov 11
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Prudential Center and Cape Liberty Cruise Port are located nearby.
Orto di Roma

Orto di Roma

3 out of 5
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rome (FCO)
Stay at this 3-star hotel in Rome. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Colosseum and Roman Forum are located nearby.
Hotel Eurogarden

Hotel Eurogarden

3 out of 5
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rome (FCO)
Stay at this 3-star business-friendly hotel in Rome. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Villa Borghese and Spanish Steps are located nearby.
Viminale View Hotel

Viminale View Hotel

3 out of 5
per person
Nov 4 - Nov 8
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rome (FCO)
Stay at this 3-star hotel in Rome. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Trevi Fountain and Roman Forum are located nearby.
Napoleon Hotel

Napoleon Hotel

4 out of 5
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rome (FCO)
Stay at this 4-star hotel in Rome. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colosseum and Roman Forum are located nearby.
Renzzi Wynwood Apartments

Renzzi Wynwood Apartments

4 out of 5
Save 100% on your flight
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Stay at this 4-star business-friendly apartment in Miami. Enjoy free WiFi, free parking, and a beach shuttle (surcharge). Popular attractions Kaseya Center and Bayside Marketplace are located nearby.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.

3-4 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Horti 14 Borgo Trastevere

Horti 14 Borgo Trastevere

4 out of 5
Rome City Centre
per person
Nov 18 - Nov 21
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
The Fifteen Keys Hotel

The Fifteen Keys Hotel

4 out of 5
Rome City Centre
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Room Mate Filippo

Room Mate Filippo

4 out of 5
Rome City Centre
per person
Nov 18 - Nov 21
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
Occidental Aran Park

Occidental Aran Park

4 out of 5
Giuliano Dalmata
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)

5-7 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
per person
Nov 6 - Nov 13
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
Relais de la Poste

Relais de la Poste

3 out of 5
Rome City Centre
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rome (FCO)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Nov 15 - Nov 20
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Miami (MIA)
Banana Bay Resort & Marina

Banana Bay Resort & Marina

3 out of 5
per person
Nov 7 - Nov 13
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)

Windward Islands Last Minute Hotel Deals

Coconut Bay Beach Resort & Spa All Inclusive
Coconut Bay Beach Resort & Spa All Inclusive
4 out of 5
Eau Piquant, Vieux Fort
Stay at this 4-star beach property in Vieux Fort. Enjoy free WiFi, free parking, and 5 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Coconut Bay Beach Resort & Spa All Inclusive
Jade Mountain Resort
Jade Mountain Resort
5 out of 5
1000 Anse Chastanet Road, Soufriere
Stay at this 5-star luxury resort in Soufriere. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Anse Chastanet Beach and Gros Piton ...
Jade Mountain Resort
Sandals St. Vincent and the Grenadines - All Inclusive Couples Only
Sandals St. Vincent and the Grenadines - All Inclusive Couples Only
4 out of 5
Buccament Bay Valley, Kingstown, Saint Andrew
Stay at this 4-star all-inclusive resort in Kingstown. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Fort Charlotte and Barrouallie ...
Sandals St. Vincent and the Grenadines - All Inclusive Couples Only
Grenadine House
Grenadine House
4 out of 5
Kingstown Park, P.O. Box 2523, Kingstown
Stay at this 4-star spa hotel in Kingstown. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Grenadine House
Cobblestone Inn
Cobblestone Inn
3 out of 5
Bay Street, Kingstown
Stay at this 3-star hotel in Kingstown. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Cobblestone Inn
Sunset Shores Beach Hotel
Sunset Shores Beach Hotel
3 out of 5
Windward Highway, Villa Beach, Villa
Stay at this 3-star beach hotel in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the restaurant and the helpful staff in our reviews. ...
Sunset Shores Beach Hotel
Beachcombers Hotel
Beachcombers Hotel
3.5 out of 5
Villa beach, Villa
Stay at this 3.5-star beach resort in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
Beachcombers Hotel
Sugar Beach, A Viceroy Resort
Sugar Beach, A Viceroy Resort
5 out of 5
Val des Pitons, Soufriere
Stay at this 5-star luxury resort in Soufriere. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Sugar Beach, A Viceroy Resort
See all 6,101 properties in Windward Islands
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.

Book the perfect getaway to Windward Islands

With Hotwire, booking your next trip to Caribbean is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Windward Islands while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Windward Islands flight and hotel package for as low as $287.

Living it up in Caribbean means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Windward Islands, Caribbean vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Windward Islands for some of the best accommodations and flight deals.

FAQs about cheap Windward Islands packages:

How to get cheap vacation deals to Windward Islands?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $102.

How much are Windward Islands packages?

Vacation packages to Windward Islands vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $287.

How to find cheap car rentals near Windward Islands?

Hotwire partners with some of the most reliable car rental companies in Caribbean to bring you the best car rental deals in Windward Islands for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Windward Islands now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Windward Islands right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.