Winchester Travel
Packages & Tours
We offer everything from basking in the Caribbean sun at an all-inclusive resort, to exploring the culture and history of Europe, snorkelling at the Great Barrier Reef, pampering yourself at a tropical Thai spa, or a romantic honeymoon in an over water bungalow in Tahiti. The choices are endless.
We’ve got you covered
Choose worry-free vacation packages with Winchester Travel. Our travel planners are constantly searching for great rates and packages and the results are often the best you’ll find in the travel industry.
Flights
Looking for a better deal on a flight? You’ll find it here. We’re always looking out for our customers—that means the best prices possible on flights to your favorite domestic and worldwide locations.
Hotels
We’re all about choice when it comes to finding you a hotel. If you’re looking for a five star resort or you have a limited budget, we can help you find the perfect hotel to suit your travel plans.
Cars
We make it easy to rent a car for your holiday. Whether you want to arrive in style or drive a hybrid during your stay, you can count on us to get you a better deal from internationally recognized vehicle rental companies.
Insurance
Protection against unexpected events like cancellations or medical emergencies is essential. We’ll help you set it up so you can focus on enjoying your trip without worrying about potential financial losses.
Upcoming Cruises
Packages & Tours
Celtic Highlights
(Ireland & Scotland)
June 15 - 27, 2025
per/person starting at:
$5995
Alaska Land & Sea
Aug 24 - Sep 7, 2025
per/person starting at:
$5195
Christmas Market Cruise
Nov 29 - Dec 7, 2025
per/person starting at:
$4995
Winchester Travel
Cruise Vacations
Boarding a cruise ship to travel to so many parts of the globe is becoming the fastest growing aspect of vacation travel. Allow us to help you plan your next cruise vacation.