Osmington Vacations from $1,039

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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.
Berkley Aparthotel

Berkley Aparthotel

3 out of 5
London City Centre
Price was $1,385, price is now $1,039 per person
$1,039
per person
Dec 31 - Jan 7
found 11 hours ago
Roundtrip flight included
New York (NYC) to London (LHR)
8/10 Very Good! (228 reviews)
The room was great. A little tricky to get in, but some of the other guests helped. Will definitely stay there again.

Reviewed on Oct 2, 2025

Urban Chic - York street

Urban Chic - York street

3 out of 5
London City Centre
Save 100% on your flight
Price was $3,506, price is now $2,343 per person
$2,343
per person
Jan 7 - Jan 13
found 12 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
No reviews
Hapimag Apartments London

Hapimag Apartments London

4.5 out of 5
London City Centre
Save 100% on your flight
Price was $1,974, price is now $1,335 per person
$1,335
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.6/10 Exceptional! (19 reviews)
Amazing stay. Beautiful location. Across from Hyde Park. Comfortable and easy walking distance to the tube.

Reviewed on Mar 5, 2023

Cleveland Residences Bloomsbury

Cleveland Residences Bloomsbury

3 out of 5
London City Centre
Price was $1,465, price is now $1,088 per person
$1,088
per person
Dec 12 - Dec 16
found 15 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.6/10 Exceptional! (86 reviews)
Arwind is excellent. Important to note that the rooms are not serviced which I didn’t realise. Everything is great.

Reviewed on Oct 23, 2025

Cleveland Residences Farringdon

Cleveland Residences Farringdon

3 out of 5
London City Centre
Price was $1,674, price is now $1,280 per person
$1,280
per person
Dec 12 - Dec 16
found 15 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.6/10 Exceptional! (12 reviews)
This property is a little gem. Great location near Farringdon station and very good cafes and eateries. Apartment was lovely and fully equipped. Communication excellent

Reviewed on Mar 18, 2025

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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 waterfront, 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

$13
per adult
Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735
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
$104 nightly
The price is $125 total per night from Nov 2 to Nov 3
$125 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (48 reviews)
Nadia at check-in to dinner service was amazing &so kind. We had the roughest day & ended up getting to the Smugglers Inn after 7p, 1 room left & she was so sweet. The food is top notch at dinner! EST we’ve had so far on our two week trip haunting all over Bath, Cornwall, & London!!!

Reviewed on Oct 18, 2025

The Smugglers Inn
Holiday Inn Express Poole by IHG

Holiday Inn Express Poole by IHG

3 out of 5
Walking Field Lane, Poole, England
Fully refundable
$70 nightly
The price is $84 total per night from Nov 2 to Nov 3
$84 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,012 reviews)
Everything about this hotel was great. Location perfect for theatre and town. Staff couldn’t do enough for us, room was clean and well appointed. Breakfast was superb - great variety to suit all tastes and constantly being replenished.

Reviewed on Oct 15, 2025

Holiday Inn Express Poole by IHG
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $79 total per night from Nov 3 to Nov 4
$79 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (706 reviews)
Lovely hotel could do with a refurbishment in reception and corridors but our room was lovely

Reviewed on Oct 20, 2025

Fairhaven Hotel
See all 2,681 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.

Find the Best Osmington Vacation Packages

Osmington Essential Information

Language
English
Currency
British pounds sterling
Max Temp Winter
50ºF
Max Temp Summer
65ºF
Top Sights
Weymouth Beach, Chesil Beach and Weymouth Pavilion

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Frequently asked questions

How much does an Osmington vacation package cost?
Offering great value package deals from $1,039 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.