Osmington Holidays from £292

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Your Osmington Holiday

Lock in a custom holiday package to Osmington and get ready for your next epic adventure. Base yourself in the neighbourhood of Wool, which is great for history and culture, for a true taste of this exciting city. Fill your schedule with visits to Weymouth Beach, Chesil Beach and Weymouth Harbour, some of the things you shouldn't miss during your trip to Osmington. Expedia will help you escape your daily routine. Tailor your holiday to Osmington to suit your travel style, whatever that may look like.

Top Osmington Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Battersea Serviced Studio Apartments
Three Falcons Hotel
Mowbray Court Hotel
The Guardsman Hotel and Residences
Middle Eight - Covent Garden - Preferred Hotels and Resorts

Osmington Essential Information

Language
English
Currency
British pounds sterling
Max Temp Winter
10ºC
Max Temp Summer
18ºC
Top Sights
Weymouth Beach, Chesil Beach and Weymouth Pavilion

Top hotels in Osmington

The Smugglers Inn

The Smugglers Inn

3 out of 5
Osmington Mills, Weymouth, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is £207 per night from 3 Aug to 4 Aug
£207
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (39 reviews)
Great
"Fabulously enjoyable, great location and great staff"

Reviewed on 25 Jul 2025

The Smugglers Inn
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
The price is £115 per night from 30 Jul to 31 Jul
£115
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very Good! (630 reviews)
"Location is fantastic!"

Reviewed on 27 Jul 2025

Fairhaven Hotel
Holiday Inn Express Poole by IHG

Holiday Inn Express Poole by IHG

3 out of 5
Walking Field Lane, Poole, England
Fully refundable
The price is £93 per night from 10 Aug to 11 Aug
£93
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"Needed more breakfast choices and Aircon was faulty"

Reviewed on 23 Jul 2025

Holiday Inn Express Poole by IHG
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.

Popular places to visit

What to do in Osmington

Frequently asked questions

Why should I book my Osmington holiday with Expedia?
Choose Expedia to plan your next big escape simply and all in the same place. Our insider tip for getting a fabulous deal on an Osmington getaway? Bundle your flights, hotel and/or hire car into a package holiday. Then add a few exciting tours and activities. Most bookings also have flexible cancellation policies, so there's no need to worry if you have to change plans. Round-the-clock assistance with making tweaks to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Osmington?
Peak season falls in January, February and July and is a thrilling time to visit — but be prepared for bigger crowds and longer queues. March, April and December are usually quieter times of the year. With average daytime temperatures of 6ºC, February is the coolest period in Osmington. The warmest month is July, when you can expect averages of 16ºC throughout the day. Whatever the weather conditions, you'll discover plenty of things to keep you busy here.
What is the top hotel for my holiday in Osmington?
Offering many of home's creature comforts, Best Western Weymouth Hotel Rembrandt will make an ideal base for your Osmington trip.
How do I get a cheap holiday to Osmington?
Browse and book everything in the one place with our Osmington holidays. You'll discover deals on hotels, flights, tours and more that'll keep your budget happy and your spirit of adventure alive. And, with more than 400 partner airlines and 321,000 hotel options around the world to choose from, you'll have the flexibility to mix and match all you want. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Osmington holiday?
Make sure your next holiday in Osmington is a memorable one by taking in its leading attractions. Weymouth Beach, Weymouth Harbour, Chesil Beach and Weymouth Pavilion are among the things we recommend seeing while you're in the city.
Do I need a visa for my Osmington holiday?
Official government websites are the best source of information on visa requirements, application procedures and any necessary documentation. Your nationality and reason for visiting, whether it be for holidays or business, will determine if you'll need a visa for Osmington. Also check that your passport is up to date and has at least six months validity remaining beyond the date of your intended return. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Osmington holiday?
Although everyone's style differs, it can be useful to have a few guidelines for what type of clothes to wear during your holiday in Osmington. We recommend looking up social media before you leave for inspiration on local dress codes or fashion trends. Daytime temperatures during February, Osmington's coolest month, are around 6ºC. July marks this destination's warmest month when average temperatures reach 16ºC. Our tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Osmington holiday include?
It depends on what sort of trip you want to have. Osmington holiday deals can include car hires, flights and hotels. You can mix and match to find the travel package that fits your needs. You can also add on activities and experiences after you've booked to land even bigger discounts. Explore a large selection of property types and select one that fits your travel needs. The most in-demand holiday rentals here are cottages and private holiday homes. With Expedia, you can easily tailor-make your Osmington retreat however you want.
Does Expedia offer Book Now, Pay Later Osmington holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Make sure you bundle your accommodation, flights and activities with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers payments in multiple transactions that suit all budgets, so you can take that well-deserved holiday sooner.
  • No-deposit holidays: Pressing the "book now" button is easier with this payment option. With no upfront fee for your getaway, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with an Osmington Expedia holiday?
Yes, and with over 400 airlines to select from across the globe, you've got lots of choice. Scroll through the available options and find out which airline best suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.