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Find a lower price online up to 24-hours prior to check-in and we’ll refund the difference.

Save up to $387^ on holiday packages when you bundle a hotel and flight.

With more than 550 airlines and 665,000 properties worldwide, it’s easy to find your best holiday.

Tips for planning your Winchester holiday

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Winchester Holiday Package Deals

Save some moolah with Wotif. Our brilliant package deals combine your flights and accommodation to make life easier. Winchester is waiting!

You could even see savings of up to $341*. And with more than 550 airlines and 665,000 worldwide properties, it's easy to craft the holiday of your dreams.

With Wotif's competitive prices, you'll be packing your bags and cruising down the runway before you know it.

Winchester Accommodation

Holidays approved? Check. Tickets booked? Check. Accommodation booked? Umm... Never fear, Wotif's got your back. You'll discover an impressive 64 accommodations in Winchester to select from.

Counting down to your upcoming holiday? Why not make the thought of it even more exciting by reserving a decadent room at the Global Luxury Suites at Kendall Square (285 Third Street) or the Global Luxury Suites at Kendall East (250 Kendall Street)? Alternatively, if all you want is a place to dump your belongings and get a good night's snooze, the Harvard Square Hotel (110 Mount Auburn Street) or the Days Hotel-Boston/Cambridge (1234 Soldiers Field Rd) will work nicely.

Car Hire in Winchester

A quick cab journey from Logan International Airport will take you to either Advantage Rent-A-Car (100 Tomahawk Drive) or Enterprise (6 Tomahawk Dr). Whichever you choose, we're sure you'll find the right car for your trip.

On the hunt for the closest vehicle hire company to the city centre? Enterprise (4 Dudley Place) is the easiest place to snag a set of keys and a comfortable ride.

Holidays to Winchester

Booked those plane tickets, packed your best thongs but clueless about Winchester? Listen up. We'll let you in on this exciting destination.

Winchester is just down the road from some major cities that should help you get your bearings. Just 4 kilometres to the north is Woburn. The town isn't far from Stoneham either. You only need to head northeast for 5 kilometres before you reach it.

Travelling alone? Excited to buddy up with a few friendly locals? With approximately 21 000 people living in this area of Massachusetts, it shouldn't take you too long to make some new friends.

How about activities that won't cost a cent? Sounds amazing, right? Well Winchester has plenty of those:

  • Are you searching for a place to visit when the clouds roll in? The National Heritage Museum and the Collection of Historical Scientific Instruments are enlightening and captivating choices to bear in mind.

  • Stop by fun and fabulous spots like the Somerville Theatre and the Alchemist. After all, you don't need to be a highbrow socialite to admire art and culture.

  • Allow your inner historian to nerd out at the Harvard University, Mount Auburn Cemetery, the Lexington Battle Green and Old Burying Ground. These important attractions tell many stories, and they won't cost you a cent to explore.

  • Spend a little time soaking up the beautiful surrounds of Winter Pond. Take a few snaps and find a place to sit — after all, we all need to slow down every now and then.

  • Receive a free and illuminating insight into the creed and culture of the area at Christ Church. Don't worry — you don't have to be especially devout to drop by this sacred site.

  • Hang out in the spectacular scenery of Boston Common, Boston Public Garden, Arnold Arboretum and Breakheart Reservation. Don't forget to take some nibbles with you.

Must-see Winchester

The Harvard University and the Semitic Museum are a big part of what make this neighbourhood so special. Be sure to stop by them during your stay.

For some people, holidays mean just one thing — shopping. To get your fix of retail therapy, check out the sales at Harvard Square. Need more ideas? Burlington Mall is the place to go for all your shopping needs. Whether you're searching for designer clothing or some flaming hot deals, this thriving mall is sure to have the goods. But you don't have to stop there. Whatever you do, don't leave behind your credit card when you go to Square One Mall. With such a variety of irresistible deals, you might need to bring some helpers to lug your bags.

Places to Visit Near Winchester

You can spend your entire time in Winchester, but you'll be missing out. Don't overlook the awesome things around you, like the Plymouth Rock. Around 60 kilometres away in Duxbury, it's the perfect excuse for a road trip.

*Savings based on all Flight + Hotel package bookings on Wotif.com from Jan 2017 to Jun 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings made with Flight + Hotel on Wotif.com from January 1, 2018 to December 31, 2018, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.