Upwey Vacations from $1,308

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Photo by Sue Wormald

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.
Smart Stays Suites in Sloane Square

Smart Stays Suites in Sloane Square

2 out of 5
London City Centre
Price was $1,725, price is now $1,308 per person
$1,308
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
7.4/10 Good! (3 reviews)
Everything went very well once I got in touch with the manager of the property who explained to me how the check in works as well as the codes etc… The flat is all brand new, super quiet and very comfortable. Excellent area and all walking distance to everything. Overall, an excellent experience! I recommend it!

Reviewed on May 6, 2025

Maddox Street - 1 bed

Maddox Street - 1 bed

2 out of 5
London City Centre
Save 100% on your flight
Price was $3,296, price is now $2,287 per person
$2,287
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
No reviews
The George Street Residences

The George Street Residences

4 out of 5
London City Centre
Save 100% on your flight
Price was $4,071, price is now $2,978 per person
$2,978
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
No reviews
Pestana Chelsea Bridge Hotel & SPA

Pestana Chelsea Bridge Hotel & SPA

4 out of 5
London City Centre
Price was $2,056, price is now $1,554 per person
$1,554
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
8.8/10 Excellent! (1,199 reviews)
Room was very clean Reception staff superb

Reviewed on Nov 10, 2025

Spacious 3-bed House With car Park Near Heathrow

Spacious 3-bed House With car Park Near Heathrow

3.5 out of 5
Heston Central
Price was $7,626, price is now $5,091 per person
$5,091
per person
Dec 12 - Dec 14
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to London (LHR)
7/10 Good! (2 reviews)
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Discover the most popular places to visit in Upwey

Weymouth Beach showing a sandy beach

Weymouth Beach

4.5/5(16 reviews)

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

4.5/5(9 reviews)

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 Upwey

Portland Shore Excursion to Jurassic Coast Highlights

Portland Shore Excursion to Jurassic Coast Highlights

$95
per adult
Portland Shore Excursion to Jurassic Coast Highlights
See all activities in Upwey

Upwey Hotel Deals

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

3 out of 5
12-18 Dorchester Road, Weymouth, England
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $125 total per night from Dec 11 to Dec 12
$125 total
Dec 11 - Dec 12
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Functional

Reviewed on Nov 9, 2025

Best Western Weymouth Hotel Rembrandt
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 16 to Nov 17
$79 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (717 reviews)
Very happy with our weekend. Really helpful staff, super appartment that really catered for our needs.A lovely mini break for my husbands 70th birthday.Would definately book again.

Reviewed on Nov 3, 2025

Fairhaven Hotel
Durdle Door Hotel

Durdle Door Hotel

3 out of 5
West Lulworth House, Main Road, West Lulworth, Wareham, England
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $140 total per night from Dec 12 to Dec 13
$140 total
Dec 12 - Dec 13
Total with taxes and fees
8.6/10 Excellent! (72 reviews)
staff and service was good and location also good

Reviewed on Nov 1, 2025

Durdle Door Hotel
See all 2,074 properties in Upwey
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 $1,308 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

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