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Windward Islands Vacation Packages

Windward Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Rio Hotel & Casino, a Destination by Hyatt Hotel

Rio Hotel & Casino, a Destination by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $344, price is now $183 per person
$183
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Book a stay at this business-friendly resort in Las Vegas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the convenient parking in our reviews. Popular attractions Bellagio Casino and Colosseum at Caesars Palace are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,338, price is now $2,746 per person
$2,746
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 5-star luxury hotel in Brooklyn. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Hotel H-Wood

Hotel H-Wood

2.5 out of 5
Price was $926, price is now $519 per person
$519
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
Stay at this hotel in Los Angeles. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Hollywood Boulevard and Hollywood Walk of Fame are located nearby.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $1,447, price is now $825 per person
$825
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 4-star eco-certified hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
Riverside Hotel

Riverside Hotel

3.5 out of 5
Price was $869, price is now $433 per person
$433
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this business-friendly hotel in Fort Lauderdale. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions Las Olas Boulevard and Las Olas Beach are located nearby.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Price was $1,155, price is now $587 per person
$587
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star apartment in Miami. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions Kaseya Center and Bayside Marketplace are located nearby.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $2,731, price is now $1,395 per person
$1,395
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 4.5-star luxury hotel in New York. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby.
Planet Hollywood Resort & Casino

Planet Hollywood Resort & Casino

4 out of 5
Save 100% on your flight
Price was $1,050, price is now $545 per person
$545
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 4-star spa resort in Las Vegas. Enjoy an outdoor pool, a full-service spa, and 9 restaurants. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions The Cosmopolitan Casino and Bellagio Casino are located nearby.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Price was $1,697, price is now $893 per person
$893
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 4-star hotel in New York. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Price was $3,561, price is now $1,917 per person
$1,917
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 5-star luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $17,849, price is now $9,922 per person
$9,922
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Save 100% on your flight
Price was $557, price is now $312 per person
$312
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
Stay at this hotel in Glendale. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Dodger Stadium and Rose Bowl Stadium are located nearby.

3-4 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Westgate Las Vegas Resort & Casino

Westgate Las Vegas Resort & Casino

4 out of 5
Save 100% on your flight
Price was $413, price is now $208 per person
$208
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Price was $1,008, price is now $548 per person
$548
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
The LINQ Hotel & Casino – A Caesars Rewards Destination

The LINQ Hotel & Casino – A Caesars Rewards Destination

4 out of 5
Las Vegas Strip
Price was $2,276, price is now $1,114 per person
$1,114
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was $869, price is now $433 per person
$433
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)

5-7 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Westgate Las Vegas Resort & Casino

Westgate Las Vegas Resort & Casino

4 out of 5
Save 100% on your flight
Price was $729, price is now $362 per person
$362
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,338, price is now $2,746 per person
$2,746
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $2,000, price is now $962 per person
$962
per person
Oct 16 - Oct 21
found 17 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Price was $1,368, price is now $670 per person
$670
per person
Oct 19 - Oct 26
found 1 day 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
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

5 out of 5
Val des Pitons, Soufrière
Stay at this 5-star luxury resort in Soufrière. 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
Sandals St. Vincent and the Grenadines Couples Only

Sandals St. Vincent and the Grenadines 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 Couples Only
Beachcombers Hotel

Beachcombers Hotel

3.5 out of 5
Villa beach, Villa
Stay at this 3.5-star family-friendly resort in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Beachcombers Hotel
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
Holiday Inn Express & Suites Diamond by IHG

Holiday Inn Express & Suites Diamond by IHG

3 out of 5
Windward Highway, Diamond
Stay at this 3-star hotel in Diamond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Argyle Beach and Villa Beach are located ...
Holiday Inn Express & Suites Diamond by IHG
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
LA Vue Boutique Hotel & Beach Club

LA Vue Boutique Hotel & Beach Club

3.5 out of 5
Indian Bay Rd, Villa, St. George
Stay at this 3.5-star beach hotel in Villa. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
LA Vue Boutique Hotel & Beach Club
See all 6,510 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.