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Our Tailor-Made Holidays

Osprey Holidays offer travellers the highest-standard tailor-made short breaks to over 90 of the world's most exciting destinations. Our award-winning team work to take the hassle out of holiday planning and create an unforgettable short break that has been designed just for you.

Why Osprey Holidays? / Our Holiday ItinerariesOur Hand-picked Hotel SelectionYour Travel OptionsMulti-Centre OptionsSpecial Offers

Why Osprey Holidays?

  • Award-winning holidays: We're proud to have been voted the best Travel Company in Western Europe at the 2023 British Travel Awards. 
  • Full financial protection: Your trip is fully ATOL and ABTA bonded.
  • Value for money: We are committed to offering our clients the very best value at all times and this means wherever possible when the opportunity arises to purchase currency at advantageous rates we will do so, as well as including any up-to-the-minute special offers from hotels and airlines.
  • Total flexibility: You choose when and how you travel and duration of your stay.
  • Personalised service: Your dedicated holiday consultant is available to assist with queries prior to and throughout your break.
  • First-class advice: Our well-travelled staff can provide expert advice on the destinations and hotels we offer.

>> Contact our expert term to begin planning your tailor-made holiday now


Our Holiday Itineraries

Our holidays are truly bespoke, every itinerary we create is completely unique and tailored to your personal holiday requirements, with as much or as little input from our City Breaks Specialists as you'd like.

Guaranteeing Flexibility and Choice

As standard, we'll arrange and book your travel and accommodation at one of the hotels within our carefully chosen selection. If you require, we can also arrange private transfers, excursions, tours, opera or concert tickets, or a full itinerary of activities for your whole stay.

We can also organise twin or triple centre holidays, group breaks or special occasions.Whatever it is you're looking for, just ask and we'll make it happen!

Travel on the Venice Simplon Orient Express to Venice and take in Verona on the same trip, combine Granada, Seville and Cordoba for a historical mini-break, or visit one of Europe's impressive Christmas markets in December.

>> Sample Itineraries

Our Hand-picked Hotel Selection

Our range of hand-picked hotels has expanded over the years, based on our own experience and that of our clients, and we're proud to offer the very best in flexibility and choice to our clients.

The hotels featured on this website are a selection of favourites but if you can't find what a hotel or destination that you are looking for, then just give us a call! We have access to many other hotels and we'd be delighted to put together a tailor-made itinerary that suits you.

Osprey Select Hotels

With our years of experience and knowledge, the Osprey Holidays team has hand-selected our favourite hotels from across our featured destinations. These hotels have a wealth of great reviews, building on both the feedback of our clients as well as our own level of quality assurance.

We offer a diverse group of Osprey Select hotels, from homely 2-star to luxurious 5-star properties, all designed to suit a wide range of tastes and budgets. The one thing they have in common is that they each meet our exceptional high standards. 

>> Find out more about our Osprey Select hotels or speak to one of our Short Break Specalists on 0131 243 8098 who will be happy to advise on your options.

Please note that we don't offer self-catered accommodation.

Your Travel Options

By Air

Whether you are travelling with a scheduled airline such as BA, KLM or Air France or a no-frills airline such as easyJet or Jet2, your holiday will be fully protected with Osprey Holidays.

We have contracts with most of the relevant scheduled airlines, however if it is cheaper or more convenient for you to use a no-frills carrier our Short Break Specalists will discuss your options.

Our guide prices are generally based on flights from London Gatwick or Heathrow, however we are of course able to book flights from our local regional airport, just ask us for details.

Also, in order to give you more options and a cheaper basic fare, many airlines now charge for extras, such as additional bags and pre-allocated seats. If you have any particular requests, let us know at the time of quotation and we will happily look at all options for you.

By Eurostar

Depart from London St Pancras, Ebbsfleet or Ashford and enjoy a leisurely journey from city centre to city centre. We can also arrange travel from most UK stations. There are convenient check in times (minimum 30 minutes prior to departure) and no separate check-in for baggage if you have no more than 2 bags or cases and one piece of hand luggage. We offer two options:

  1. Standard Class: Enjoy comfort in a spacious air-conditioned carriage. Onboard buffet cars offer an array of snacks, meals and alcoholic and non-alocoholic beverages.
  2. Standard Premier: Quiet, spacious surroundings with extra legroom in exclusive carriages. Staff are on hand to serve your complimentary meal at your seat. As for drinks, enjoy tea, coffee and soft drinks, or maybe relax with a glass of wine or beer.

Pre-Booked Transfers

Take the hassle out of getting to and from your hotel by pre-booking transfers before you leave.

Private Transfers: Your personal driver will be waiting for you upon arrival to take you to your destination. Larger vehicles can be pre-booked depending on the size of party travelling.

Shared Shuttle Transfers: A good value option to get to your desired destination, these have multiple drop off and pick up points and there may be a waiting time involved. Journey times will generally be slightly longer than private transfers.

Please note that shared transfers are not available in every city. Both transfer types will pick you up from your arrival point and take you to your hotel, however whilst the supplier endeavours to operate a door-to-door service, on some occasions this may not be possible due to local restrictions such as pedestrian areas or road closures. Where these restrictions apply drivers will drop and collect you from the nearest accessible point.

Multi-Centre Options

Why not make the most of your time away by enjoying a multi-centre holiday? Many European locations are easy to combine and we can arrange the perfect itinerary before you leave.

Should you wish to opt for a multi-centre holiday we are able to book rail journeys on the continent for you. Whether you want to travel First or Standard Class, or even by overnight sleeper, simply ask our City Break Specalists who will be happy to put together a tailor-made itinerary for you.

Why not extend your trip to Paris by experiencing the magical Cote D’Azur, or after exploring the wonders of Rome a relaxing trip down to the Neapolitan Riviera might be on the cards. The exciting Spanish cities of Madrid and Barcelona make the perfect two centre option and why just visit Prague when you can combine Vienna and Budapest too? The possibilities are endless and we would be delighted to discuss options with you.

Latest Offers

Throughout the range of city break destinations that we offer you'll find a huge number of special offers and discounts for selected dates. We look forward to assisting you with your travel plans.

>> View our latest offers

Request your bespoke holiday itinerary now - call our Short Breaks team on 0131 243 8098 for your tailor-made quote.