Vacation Packages from Boston, MA | CheapCaribbean

View our Accessibility Statement Skip to Main Content Link will open in a new tab.

Destinations
DESTINATIONS
- Anguilla
- Antigua
- Aruba
- Bahamas
- Barbados
- Belize
- Bermuda
- Bonaire
- British Virgin Islands
  - Tortola
- Cartagena
- Cayman Islands
- Costa Rica
- Curaçao
- Dominican Republic
- Grenada
- Jamaica
- Mexico
  - Acapulco
  - Cancun
  - Cozumel
  - Huatulco
  - Ixtapa / Zihuatanejo
  - Los Cabos
  - Manzanillo
  - Mazatlan
  - Puerto Vallarta
  - Riviera Maya
  - Tulum
- Nicaragua
- Panama
- Puerto Rico
- St Kitts & Nevis
- St Lucia
- St Maarten / St Martin
- Turks & Caicos
- U.S. Virgin Islands
View all destinations
Deals
TRAVEL DEALS
DEALS BY DESTINATIONS
DEALS BY INTEREST
View all deals
Resorts
FEATURED RESORT BRANDS
- Breathless
- Dreams
- Iberostar
- Meliá Hotels & Resorts
- Now
- Occidental
- Palladium
- Paradisus by Meliá
- Riu
- Secrets
- Sunscape
- TRS
- Zoëtry
MORE RESORT BRANDS
- Bahia Principe
- Be Live
- Blue Diamond
- Bluebay
- Catalonia
- Comfort Suites
- Couples
- Decameron
- Divi
- El Cid
- Elegant
- Elite Island
- Fairmont
- Hard Rock Hotels
- Hilton
- Holiday Inn
- Karisma
- La Coleccion by Fiesta Americana
- Majestic
- Marriott
- Oasis
- Ocean
- Original
- Princess
- Pueblo Bonito
- Radisson
- Renaissance
- Royal Hideaway Luxury Hotels & Resorts
- Sandos
- Sheraton
- Solaris
- Turks & Caicos Collection
- Velas
- VIK
- Villa Group
- Viva Wyndham
- Westin
- Wyndham
View all resort brands
Get Help
GET HELP
BE A #TRUEBEACHLOVER
- Facebook
- TikTok
- Instagram
- Pinterest
- Read Our Blog
Sign In
MY ACCOUNT
Get Help
GET HELP
BE A #TRUEBEACHLOVER
- Facebook
- TikTok
- Instagram
- Pinterest
- Read Our Blog

Caribbean

Aruba

Bahamas

Dominican Republic

Jamaica

Puerto Rico

Punta Cana

St. Martin/St. Maarten
Mexico

Cancun

Cozumel

Los Cabos

Puerto Vallarta

Riviera Maya
Latin America

Cartagena

Costa Rica

Panama

View all
View all
Travel Deals

All-Inclusive Packages

All-Inclusive Resorts

Vacation Packages

Last-Minute Deals

Promo Code Deals

MORE Perks

Noble Beach Prize Winners

Discounts for Heroes
Deals by Destination

Aruba All-Inclusive Vacations

Bahamas All-Inclusive Vacations

Cancun All-Inclusive Vacations

Jamaica All-Inclusive Vacations

Los Cabos All-Inclusive Vacations

Puerto Vallarta All-Inclusive Vacations

Punta Cana All-Inclusive Vacations

Riviera Maya All-Inclusive Vacations
Deals by Interest

Adults-Only Vacations

Best Beach Vacations

Cheap Vacation Packages

Family-Friendly Vacations

Golf Vacations

Luxury Vacations

Romantic Vacations

Spa & Wellness Vacations
View all
Find My Trip

Sign In

Explore Our Beaches

Find Your Beach Vacation

ALL FILTERS

ALL FILTERS

ALL FILTERS

Sort by

Destination

Antigua (9)
Aruba (20)
Cancun - Cancun AND Riviera Maya (69)
Cancun - Cancun Hotels (37)
Cancun - Riviera Maya Hotels (76)
Cozumel (8)
Dominican Republic, Puerto Plata (7)
Dominican Republic, Punta Cana (60)
Fort Lauderdale (7)
Fort Myers (7)
Hawaii, Honolulu, Oahu (14)
Hawaii, Kona, Island of Hawaii (5)
Jamaica, Montego Bay (35)
Los Cabos (22)
Puerto Rico, San Juan (3)

Theme

Adults Only (98)
Culture (35)
Dining (250)
Diving (145)
Family (188)
Gaming (37)
Golf (117)
Luxury (24)
Mystery Deal (1)
Nightlife (156)
On the Beach (322)
Romance (218)
Shopping (88)
Snorkeling (124)
Spa (227)
Wedding (212)

Sort by

Recommended
Hotel Name (Ascending)
Hotel Name (Descending)
Price (Low to High)
Price (High to Low)

Theme

Adults Only (98)
Culture (35)
Dining (250)
Diving (145)
Family (188)
Gaming (37)
Golf (117)
Luxury (24)
Mystery Deal (1)
Nightlife (156)
On the Beach (322)
Romance (218)
Shopping (88)
Snorkeling (124)
Spa (227)
Wedding (212)

Destination

Antigua (9)
Aruba (20)
Cancun - Cancun AND Riviera Maya (69)
Cancun - Cancun Hotels (37)
Cancun - Riviera Maya Hotels (76)
Cozumel (8)
Dominican Republic, Puerto Plata (7)
Dominican Republic, Punta Cana (60)
Fort Lauderdale (7)
Fort Myers (7)
Hawaii, Honolulu, Oahu (14)
Hawaii, Kona, Island of Hawaii (5)
Jamaica, Montego Bay (35)
Los Cabos (22)
Puerto Rico, San Juan (3)

5 Hotels

5 Hotels

TripAdvisor Traveler Rating

Reviews

Pineapple Beach Club - All Inclusive

4 Star Hotel

TripAdvisor Traveler Rating

Reviews

All-Inclusive

Antigua

Best Priced Departure Dates

2025: May 3 - Aug 15

3 Nights Hotel + Flight From

Get Price Includes Taxes + Fees
TripAdvisor Traveler Rating

Reviews

Carlisle Bay Resort - All Inclusive

5 Star Hotel

TripAdvisor Traveler Rating

Reviews

All-Inclusive

Antigua

Best Priced Departure Dates

2025: May 3 - Aug 15

3 Nights Hotel + Flight From

Get Price Includes Taxes + Fees
TripAdvisor Traveler Rating

Reviews

Royalton Antigua, An Autograph Collection - All Inclusive

5 Star Hotel

TripAdvisor Traveler Rating

Reviews

All-Inclusive

Antigua

Best Priced Departure Dates

2025: May 3 - Aug 15

4 Nights Hotel + Flight From

Get Price Includes Taxes + Fees
TripAdvisor Traveler Rating

Reviews

Galley Bay Resort and Spa - All Inclusive

4 Star Hotel

TripAdvisor Traveler Rating

Reviews

All-Inclusive

Antigua

Best Priced Departure Dates

2025: May 3 - Aug 15

5 Nights Hotel + Flight From

Get Price Includes Taxes + Fees
TripAdvisor Traveler Rating

Reviews

Hammock Cove Antigua - All Inclusive

5 Star Hotel

TripAdvisor Traveler Rating

Reviews

All-Inclusive

Antigua

Best Priced Departure Dates

2025: May 3 - Aug 15

5 Nights Hotel + Flight From

Get Price Includes Taxes + Fees

We're sorry; there are no hotels that match the criteria you have selected.

WHO WE ARE

About Us
Why Book with Us
Travel Protection Plus
In the News
Careers
Resorts

SUPPORT

Frequently Asked Questions
Health & Safety Measures
Payment Options
Group Travel
Accessibility Statement
Gen/Cancel Terms & Conditions
Privacy Policy

MY ACCOUNT

Sign In
Sign Up
Find Your Reservation
Check Travel Credits

BE A #TRUEBEACHLOVER

GET MORE VALUE

Sign up to get MORE deals, MORE insider tips on the best beaches and $100 off your first vacay (valid on 6 nights or more).

* Please enter a valid email address

BOOM! DONE.

Keep an eye on your inbox for your $100. In the meantime, get to work on that "out of office" message!

Copyright © 2025 CheapCaribbean TripAdvisor logo