A gravel path through a lush green landscape with dense vegetation on either side.
Photo by Adrian Farwell
Open Photo by Adrian Farwell

Tiptoe Holidays from £104

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Your Tiptoe Holiday

The stress-free way to experience this interesting city is with a tailor-made Tiptoe holiday package. Stay in the neighbourhood of Southbourne, which is good for dining, shopping and bars and pubs or go someplace else — our package deals are all about you. Any trip to Tiptoe needs a well-thought-out itinerary. Fill yours with attractions like Milford on Sea Beach, Hurst Beach and Lymington Sea Water Baths. Whatever your travel plans or the size of your budget, putting together a tailored Tiptoe holiday is a cinch with Expedia.

Top Tiptoe flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 22 Jan - 24 Jan

    The Poacher Inn + Flight

    Hook
    2 nights
    3.0 star property
    8.2/10 - Very good (111 reviews)
    "My wife and I only stayed one night in this Quaint Inn that has a lovely vibe and we would definitely stay here again. The room was nice, clean and had plenty of tea/coffee. Couldn't sample the breakfast because we were up and away early. However, we did have our evening meal here and can say the food was very good. The staff were very friendly, professional and helpful. We chose the Poachers Inn based on previous reviews and location (being 20-30mins away from Farnborough international..."
    Reviewed September 26, 2026
    Return • Glasgow (GLA) - Southampton (SOU)
    GLA - STN • Direct STN - GLA • Direct
    £130
    £104
    per traveller
    found 21 hours ago
    The Poacher Inn
  • 23 Dec - 28 Dec

    The Pilot Boat Inn + Flight

    Bembridge
    5 nights
    3.5 star property
    7.8/10 - Good (30 reviews)
    "A band was playing until 11.10pm on Friday night which was above the legal 11pm time limit.. (this was the time I was told this would be the time the band would finish. My room was above the band- so it's worth avoiding that room! It was called “Port” Breakfast was ok other than the mouldly brown bread, I didn't check if the kitchen was clean. Didn't get breakfast on the 2nd morning as I arrived downstairs at 9.15 am - doors all locked up. The room was clean and tidy - staff friendly"
    Reviewed October 5, 2026
    Return • Jersey (JER) - Southampton (SOU)
    JER - LHR • Direct LHR - JER • Direct
    £474
    £372
    per traveller
    found 1 day ago
    The Pilot Boat Inn
  • 23 Dec - 28 Dec

    The Q Hotel + Flight

    Shanklin
    5 nights
    3.0 star property
    8.2/10 - Very good (213 reviews)
    Return • Jersey (JER) - Southampton (SOU)
    JER - LHR • Direct LHR - JER • Direct
    £581
    £457
    per traveller
    found 1 day ago
    The Q Hotel
  • 23 Dec - 28 Dec

    Orange Grove Hotel & Gardens + Flight

    Southampton
    5 nights
    3.0 star property
    8.4/10 - Very good (403 reviews)
    "Well located for our purposes. We had several meals in the hotel. From breakfast through to dinner and Sunday lunch. Everything we tried was excellent. Room was massive with equally huge bathroom. Only slight issue was that the TV/remote were not responsive and other people were logged into Netflix and prime but the not so good remote wouldn’t let us adjust this."
    Reviewed November 2, 2026
    Return • Jersey (JER) - Southampton (SOU)
    JER - LHR • Direct LHR - JER • Direct
    £472
    £389
    per traveller
    found 1 day ago
    Orange Grove Hotel & Gardens
  • 23 Dec - 28 Dec

    Sentry Mead + Flight

    Totland Bay
    5 nights
    3.5 star property
    9.8/10 - Exceptional (112 reviews)
    "If I had to run an hotel - this would be it! Every aspect was excellent!"
    Reviewed November 2, 2026
    Return • Jersey (JER) - Southampton (SOU)
    JER - LHR • Direct LHR - JER • Direct
    £626
    £519
    per traveller
    found 1 day ago
    Sentry Mead

Tiptoe Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

Why should I book my Tiptoe holiday with Expedia?

Choose Expedia to plan your next big escape simply and all in one convenient place. Our insider tip for bagging a terrific deal on a Tiptoe getaway? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a couple of awesome tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to worry if you have to switch up your travel agenda. Round-the-clock help with making tweaks to your trip is available via our Customer Service Portal link.

When is the best time of year to holiday in Tiptoe?

If you love the buzz of peak season, visit Tiptoe in April, June and September. If you prefer a more relaxed vibe, March, November and December are better times to visit. To get an idea of what type of weather you can experience, the average temperature during the day in January, the coolest time of year in Tiptoe, is 6ºC. The warmest period here is July, when temperatures are around 17ºC.

What is the top hotel for my holiday in Tiptoe?

Create unforgettable memories in Tiptoe by choosing Macdonald Elmers Court Hotel as your home-away-from-home and gateway to adventure and exploration.

How do I get a cheap holiday to Tiptoe?

If you love getting an amazing deal, bundle your bookings into a Tiptoe holiday. Whether you're searching for hotels, flights, activities or hire cars, you can book them all in one place. You'll have loads of choice at your fingertips too. Expedia has more than 400 airlines and 321,000 hotels around the world to choose from. Fly with who you want, stay anywhere you like and save a tidy sum — now that's the perfect holiday! Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Tiptoe holiday?

Offering popular attractions like Milford on Sea Beach and Hurst Castle, a holiday in Tiptoe is filled with fun things to see and do. Lymington Sea Water Baths and Hurst Beach are two other sights also worth exploring.

Do I need a visa for my Tiptoe holiday?

Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for your visit, whether it be for work or holidays, will determine if you'll need a visa for Tiptoe. Also double-check that your passport is up to date and has at least six months validity remaining after the date of your intended return. Finalise all your travel planning well in advance to avoid any last-minute surprises.

What should I wear on my Tiptoe holiday?

Though everyone's style differs, it can be helpful to have some guidelines for what kind of clothes to wear on your holiday in Tiptoe. We recommend searching style blogs before you leave so you can blend in like a local. Daytime temperatures during January, Tiptoe's coolest month, average 6ºC. July marks this city's warmest month when the average reaches 17ºC. Our tip? Take the guesswork out of packing and check the weather forecast.

What does an Expedia Tiptoe holiday include?

Hotels, flights and a cool car for all your road trip adventures. Simply choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of tours and activities and watch your savings pile up. When it comes to crafting your Tiptoe holiday, you're in charge! Discover a large selection of property types and pick one that matches your travel needs. The most in-demand holiday rentals here are private holiday homes and cottages. With Expedia, it's easy to customise your Tiptoe escape any way you want.

Does Expedia offer Book Now, Pay Later Tiptoe holidays?

We certainly do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Be sure to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions sounds right for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
  • No-deposit holidays: If no upfront fee for your getaway makes clicking that "book now" button more stress-free, choose a no-deposit holiday plan with Klarna so you can Book Now, Pay Later!

Can I choose my airline with a Tiptoe Expedia holiday?

With a holiday package, you're in charge. Whether you'd prefer to fly to Tiptoe in coach or first class, simply select from the available airline options. Expedia has access to more than 400 partner airlines around the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.