Exclusive Main Street Vacation Deals
Main Street vacation package deals
Price found within the past 48 hours. Click for updated prices.
Coconut Tree Villa
Price was $2,595, price is now $1,893 per person
$1,893
per person
May 23 - May 29
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Tortola (EIS)
This hotel features a terrace, laundry facilities, and free self parking. A garden, concierge services, and barbecue grills are also on offer.
Bitter End Yacht Club
Save 100% on your flight
Price was $7,719, price is now $5,698 per person
$5,698
per person
May 23 - May 29
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Tortola (EIS)
This smoke-free hotel features a marina and 2 restaurants. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with a free kid's club and kayaking, and babysitting is an added bonus.
Scrub Island Resort, Spa & Marina
Price was $2,476, price is now $1,930 per person
$1,930
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Enjoy a meal in one of the 5 restaurants and freebies like WiFi in public areas and a roundtrip airport shuttle.
Saba Rock Resort
Save 100% on your flight
Price was $4,028, price is now $3,166 per person
$3,166
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
This award-winning resort features a marina and 2 restaurants. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A garden, luggage storage, and laundry facilities are also on offer.
Rosewood Little Dix Bay
Save 100% on your flight
Price was $18,332, price is now $14,860 per person
$14,860
per person
May 23 - May 29
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Tortola (EIS)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare.
Cane Garden Bay Beach Hotel
Price was $2,445, price is now $1,989 per person
$1,989
per person
May 23 - May 29
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Tortola (EIS)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and free perks like continental breakfast and free self parking.
Top Main Street hotel deals
Maria's By the Sea Hotel
Road Town Road Town Tortola
$275 nightly
The price is $300 total per night
$300 total
Mar 18 - Mar 19
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Dry cleaning, concierge services, and wedding services are also on offer.
Pool
Free WiFi
Nanny Cay Resort and Marina
Nanny Cay Road Town NA
$215 nightly
The price is $235 total per night
$235 total
Mar 30 - Mar 31
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
The Moorings Yacht Club Hotel
Road Town Road Town Tortola
Free Cancellation
Reserve now, pay when you stay
$323 nightly
The price is $352 total per night
$352 total
Mar 17 - Mar 18
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. A coffee shop, a garden, and a grocery/convenience store are also on offer.
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.