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Boston, Winter, Holiday Season
We confirmed all prices were correct when we reviewed this deal, but that was a quite a while ago so they may have changed. Feel free to check if it’s still available, and join us on our WhatsApp channel below so you never miss a new review.

Walking in a winter wonderland ❄️ Check out this Boston 5-night break with ✈️

Say what?! A 5-night stay is cheaper than three 🥂🤩

From £477 pp

Published by
Hannah G·15/12/2023

Calling all winter wonderland chasers, do we have a snowy city break for you. Say hello to Boston in February. February is usually Boston's snowiest month. The cold weather is coupled with sunny days, so for us, that's the perfect time to see Beantown.

Fly to Boston and enjoy five nights at the Staypineapple, A Delightful Hotel, for £477. This is a super price for a boutique hotel and transatlantic flight package. Plus, the 5-night stay is somehow cheaper than three nights. We're not gonna argue with that...

So what's the catch? Well, firstly the flight isn't direct, you will have a stop off in Barcelona along the way. If indirect flights are not your bag, you can enjoy this same deal with direct flights for £585. Fear not, we've got your back.

This deal is a great excuse to discover the cultural city of Boston and dive deep into American history. Not to mention visit its world-class museums (which remain open throughout the year), and catch a Boston Bruins and Celtics basketball game at TD Garden.

From ice skating on Frog Pond and visiting the Snowport Winter Village in the seaport to having dinner in an igloo at the Envoy Hotel's Lookout Rooftop Bar, Boston has seriously fun winter activities to make your winter trip truly memorable.


  • Travel on 1 February from London for the best price

  • Other travel dates, departure airports and durations are available but they may cost more

  • Transfers and checked luggage are not included

  • Based on two sharing, ATOL protected and available on Kayak

Additional Information

We might be Pirates, but we’re an honest bunch. We check all our deals when we review them to make sure everything is available. Here’s the catch: with deals this hot, things change quickly: flight prices fluctuate, hotel rooms sell out, currencies yo-yo. Mainly, demand for the best deals means the lowest prices don’t last long. But, if you’ve missed out this time, don’t worry: we’re working on more great offers.

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