Osmington Vacation Packages

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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.

Top Osmington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Villa Kensington

The Villa Kensington

3.5 out of 5
London City Centre
Price was CA $1,945, price is now CA $1,285 per person
CA $1,285
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8/10 Very good! (956 reviews)
quite acceptable for a one night stop over

Reviewed on Jul 2, 2026

Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Price was CA $2,871, price is now CA $1,871 per person
CA $1,871
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9/10 Wonderful! (1,739 reviews)
Mediocre stay. No options for vegetarian sausages etc

Reviewed on Jul 13, 2026

Three Falcons Hotel

Three Falcons Hotel

4 out of 5
City of Westminster
Price was CA $2,015, price is now CA $1,320 per person
CA $1,320
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8.8/10 Excellent! (641 reviews)
My partner and me stayed for one night. This place has great potential but they need to work on several areas. It was very clean the room was very nice and the air con was spot on. Negatives breakfast. Yes it’s a bonus getting a breakfast in a London hotel but this was very poor. No hot water in morning so no shower which was very very disappointing. No explanation as to why . Barman in evening when we returned after watching London show not particularly receptive . A bit of courtesy goes a long way. In summary lots of things to be improved but with a bit of effort this will be achievable

Reviewed on Jul 7, 2026

Oldfields House

Oldfields House

4 out of 5
Oldfield Park
Price was CA $2,721, price is now CA $1,787 per person
CA $1,787
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
9/10 Wonderful! (1,001 reviews)
Beautiful, out of the way b&b. The staff are so nice, and helpful.

Reviewed on Jul 12, 2026

Chancery Lane by Viridian Apartments

Chancery Lane by Viridian Apartments

4 out of 5
London City Centre
Price was CA $6,832, price is now CA $4,554 per person
CA $4,554
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to London (LHR)
8/10 Very good! (3 reviews)
The apartment was great - getting in the property was tricky at first as code didn't work and property manager didn't respond but beyond that was good. the hallway and elevator was very dirty on arrival. the apartment was good though. nice size/quality

Reviewed on Jun 15, 2025

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Osmington Hotel Deals

The Smugglers Inn

The Smugglers Inn

3 out of 5
Osmington Mills Weymouth England
Fully refundableReserve now, pay when you stay
The price is CA $293 per night from Jul 26 to Jul 27
CA $293
CA $352 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (72 reviews)
"Not enough natural ventilation in the room given there is no air conditioning."

Reviewed on Jul 12, 2026

The Smugglers Inn
Fairhaven Hotel

Fairhaven Hotel

3 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
The price is CA $158 per night from Jul 19 to Jul 20
CA $158
CA $190 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (828 reviews)
"Always enjoy our stay, we have stayed in the Fairhaven 3 years on the trot and the staff are all very helpful and nice"

Reviewed on Jul 12, 2026

Fairhaven Hotel
Sandbanks Hotel

Sandbanks Hotel

4 out of 5
15 Banks Road Poole England
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from Jul 30 to Jul 31
CA $300
CA $360 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very good! (900 reviews)
"Big space hotel very dated and no a/c"

Reviewed on Jul 12, 2026

Sandbanks Hotel
See all 3,164 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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What to do in Osmington

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

Pauls Walking Tours - Sundays at 10:00am

CA $19
per adult
Pauls Walking Tours - Sundays at 10:00am
Half-Day Guided E-Bike Tour Portland with Brunch

Half-Day Guided E-Bike Tour Portland with Brunch

CA $244
per adult
Half-Day Guided E-Bike Tour Portland with Brunch
Nordic Walking Tour of Weymouths Iconic Landmarks

Nordic Walking Tour of Weymouth’s Iconic Landmarks

CA $19
per adult
Nordic Walking Tour of Weymouth’s Iconic Landmarks
See all activities in Osmington

Frequently asked questions

How much does an Osmington vacation package cost?
Offering excellent value package deals from CA $1,285 on Expedia, you'll be surprised at how little a vacation to Osmington costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Osmington?
To score cheap Osmington vacation packages, organize your getaway outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Osmington?
We recommend planning an Osmington vacation for at least 2 days. This will allow you plenty of time to tick off top attractions including Chesil Beach and Weymouth Pavilion, and also check out neighbourhoods like Preston and Overcombe. You could even make time for one or two day trips from Osmington.
How to find the best Osmington package deals?
Use Expedia's filter tool to help you find some of the best Osmington package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Osmington package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Osmington vacation as a package?
You can enjoy significant savings on your next Osmington escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Osmington?
If you're considering a spontaneous Osmington adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Osmington?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Osmington.
  2. Budget wisely: Besides the cost of your accommodations, you should consider other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Osmington.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to get to in Osmington. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Osmington vacation package.

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