Upwey Vacations from $1,042
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Your Upwey Vacation
Say bye-bye to the worries of planning and hello to a Upwey vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Puncknowle, which is good for nature, history and culture. Fill your schedule with tours of Weymouth Beach, Chesil Beach and Weymouth Harbour, some of the top attractions you should see during your trip to Upwey. Whatever your travel plans or the size of your budget, organizing a tailored Upwey vacation is simple with Expedia.
The Latest Upwey vacation packages
Price found within the past 48 hours. Click for updated prices.
What to do in Upwey
Portland Shore Excursion to Jurassic Coast Highlights
$89
per adult
Guided E-Bike Tour of the Isle of Portland, Dorset
$176
per adult
Upwey Hotel Deals
Fairhaven Hotel
Fairhaven Hotel, 37 Esplanade Weymouth England
$81 nightly
$97 total
Oct 4 - Oct 5
Total with taxes and fees
The Jubilee Hotel East- with Spa Facilities
143-146 The Esplanade Weymouth England
Fully refundable
$77 nightly
$93 total
Oct 4 - Oct 5
Total with taxes and fees
7.2/10 Good! (508 reviews)
"The children's bedroom was not clean, under the mattress on bunk bed was months of dust and grime, the carpet hadn't been hoovered. Sweets and rubbish on the floor under the bunk bed. The children safety lock has only 1 bent scew, as a fixing.and hanging off."
Reviewed on Sep 2, 2026
Sleeping Bear Hotel Dorchester
32 High West Street, 32 Dorchester England
Fully refundableReserve now, pay when you stay
$64 nightly
$76 total
Oct 4 - Oct 5
Total with taxes and fees
8.8/10 Excellent! (601 reviews)
"Excellent hotel, highly recommended"
Reviewed on Sep 1, 2026
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 Upwey Vacation Packages
Upwey Essential Information
Language | English |
|---|---|
Currency | British pounds sterling |
Top Sights | Weymouth Beach, Chesil Beach and Weymouth Pavilion |
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Frequently asked questions
How much does an Upwey vacation package cost?
Offering great value package deals from $1,042 on Expedia, you'll be pleasantly surprised at how much a vacation to Upwey costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Upwey?
March, April and December are the best times to search for cheap Upwey vacation packages. Choosing to travel in less busy months means you can usually find reduced prices on accommodations and flights.
How many days is enough for Upwey?
With a well-organized itinerary, you can easily tick off the most popular Upwey sights in a few days. But if you prefer to venture off the beaten track or take day trips, think about booking your Upwey vacation for longer.
How to find the best Upwey package deals?
Bagging a cheap Upwey package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Upwey package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Upwey vacation as a package?
You can enjoy significant savings on your next Upwey getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Upwey?
If you've got your Upwey vacation dates locked in, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Upwey vacation packages?
Your Upwey getaway is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
Explore a world of travel with Expedia
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- Sandsfoot Castle
- Kingston Maurward Park and Gardens
- Visit Broadwey
- Weymouth Harbour
- Abbotsbury Swannery
- Visit Poundbury
- Abbotsbury Children's Farm
- Visit Chickerell
- Tutankhamun: The Exhibition
- Nothe Fort
- The Olympic Rings Stone Sculpture
- Weymouth Vacations
- Verne High Angle Battery
- Visit Whitcombe
- Durdle Door Beach
- Maiden Castle
- Durdle Pier
- Abbotsbury Sub-Tropical Gardens
- Sea LIFE Centre Weymouth
- Chesil Beach
- Dorchester Vacations
- Castle Cove Beach
- Visit Weymouth
- Durdle Door
- Weymouth Beach
- Portland Vacations
- Visit South Coast
- Portland Harbour
- Tolpuddle Martyrs Museum
- Fantasy Island Fun Park
- Visit Dorset
- Hardy Monument
- Portland Castle
- Visit Dorchester
- Dorset Vacations
- Church Ope Cove
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
