Osmington Vacations from $756

Book a Hotel + Flight or Car together to unlock savings

Your Osmington Vacation

Lock in a custom vacation package to Osmington and get ready for your next epic adventure. Base yourself in the neighborhood 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 vacation to Osmington to suit your travel style, whatever that may look like.

The Latest Osmington vacation packages

Price found within the past 48 hours. Click for updated prices.
Westpoint Hotel

Westpoint Hotel

3 out of 5
London City Centre
Price was $1,139, price is now $756 per person
$756
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
6.8/10 (1,000 reviews)
The location of hotel is close to Paddington station, which is very convenient to travel around in London via public transportation.

Reviewed on Aug 12, 2025

THE KNIGHT OF NOTTINGHILL

THE KNIGHT OF NOTTINGHILL

3.5 out of 5
Notting Hill
Price was $1,606, price is now $1,150 per person
$1,150
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
8.8/10 Excellent! (22 reviews)
I booked this last minute when another hotel booking fell through. All I knew was that I liked the area it was in and needed a place to sleep but I was so pleasantly surprised by how nice and cute it was. Highly recommend for solo travelers!

Reviewed on Sep 10, 2024

Staines City Centre by Charles Hope

Staines City Centre by Charles Hope

3.5 out of 5
Staines Town Centre
Price was $1,206, price is now $890 per person
$890
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
8.8/10 Excellent! (35 reviews)
Nice and spacious apartment, I love it!

Reviewed on Jul 7, 2025

1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
Save 100% on your flight
Price was $4,108, price is now $2,803 per person
$2,803
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to London (LHR)
9.4/10 Exceptional! (283 reviews)
Lovely property. Balcony was a great perk during my stay.

Reviewed on Aug 16, 2025

Maddox Street - 3 bed

Maddox Street - 3 bed

2 out of 5
London City Centre
Save 100% on your flight
Price was $3,691, price is now $2,568 per person
$2,568
per person
Oct 26 - Oct 30
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to London (LHR)
No reviews
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Discover the most popular places to visit in Osmington

Weymouth Beach showing a sandy beach

Weymouth Beach

Breathe in the salty sea air, savor hot fish and chips and take photos of the coastline as you amble along the Esplanade that follows the gentle curve of this beach.

Weymouth Beach
Pebbles everywhere! Beautiful crystal blue sea. #waterlust #sea #waves #chesilbeach

Chesil Beach

If a restful vacation is part of your travel plans, Chesil Beach might be the perfect place to seek out during your trip to Weymouth. Stroll along the area's seaside, or simply savor its charming coffeehouses.

Chesil Beach
Weymouth Harbour

Weymouth Harbour

Explore the waterfront in Weymouth with a trip to Weymouth Harbour. Wander the area's seaside or simply enjoy one of its charming coffeehouses.

Weymouth Harbour

What to do in Osmington

Pauls Walking Tour - Sat & Sundays at 10:00am - or Group book on 07851934735

Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735

$14
per adult
Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735
Portland Shore Excursion to Jurassic Coast Highlights

Portland Shore Excursion to Jurassic Coast Highlights

$99
per adult
Portland Shore Excursion to Jurassic Coast Highlights
See all activities in Osmington

Osmington Hotel Deals

The Smugglers Inn

The Smugglers Inn

3 out of 5
Osmington Mills, Weymouth, Weymouth, England
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $152 total per night from Sep 7 to Sep 8
$152 total
Sep 7 - Sep 8
Total with taxes and fees
The Smugglers Inn
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $85 total per night from Sep 7 to Sep 8
$85 total
Sep 7 - Sep 8
Total with taxes and fees
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
$90 nightly
The price is $108 total per night from Sep 28 to Sep 29
$108 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express Poole by IHG
See all 2,691 properties in Osmington
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.

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Frequently asked questions

How much does an Osmington vacation package cost?
Offering great value package deals from $756 on Expedia, you'll be pleasantly surprised at how much a vacation to Osmington costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osmington?
March, April and December are the best times to look for cheap Osmington vacation packages. Opting to travel in quieter months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Osmington?
With a well-organized itinerary, you can easily visit the main Osmington attractions in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Osmington vacation for longer.
How to find the best Osmington package deals?
Use Expedia's filters to help you find some of the best Osmington package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Osmington package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book an Osmington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Osmington vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Osmington?
Secure incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Osmington trip.
Does Expedia offer Book Now, Pay Later Osmington vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Osmington vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.