Upwey Vacations from $1,570

Book a Hotel + Flight or Car together to unlock savings

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.
OYO The Kilburn Arms

OYO The Kilburn Arms

3 out of 5
Queen's Park
Price was $3,365, price is now $1,570 per person
$1,570
per person
Jun 17 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to London (LHR)
8/10 Very Good! (21 reviews)
Clean room, comfy bed, hot shower. Nearby corner shop and Tesco metro. Short walk to cafes etc at Queens Park. The food in the pub was very good. My only complaint is that one of the bar staff had a runny nose, would blow it and NOT WASH HIS HANDS and go on to serve people.Basic hygiene!!! I am glad we had eaten before we noticed this..

Reviewed on Apr 5, 2026

The Savoy

The Savoy

5 out of 5
London City Centre
Price was $3,563, price is now $2,688 per person
$2,688
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.8/10 Exceptional! (1,004 reviews)
Incredible hotel, couldn’t fault it from the moment we walked in to the moment we checked out. Pure luxury

Reviewed on May 16, 2026

One Aldwych

One Aldwych

5 out of 5
London City Centre
Price was $3,235, price is now $2,507 per person
$2,507
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.6/10 Exceptional! (628 reviews)
Everything was wonderful

Reviewed on Apr 28, 2026

Sea Containers London

Sea Containers London

5 out of 5
London City Centre
Price was $2,442, price is now $1,914 per person
$1,914
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.4/10 Exceptional! (2,556 reviews)
Great staff and very cool bar on the roof.

Reviewed on May 15, 2026

The Beaumont Mayfair

The Beaumont Mayfair

5 out of 5
London City Centre
Price was $3,393, price is now $2,674 per person
$2,674
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.8/10 Exceptional! (308 reviews)
Perfect location lovely staff will stay there again!!

Reviewed on Apr 20, 2026

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Discover the most popular places to visit in Upwey

Weymouth 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
Chesil Beach, Weymouth, Dorset, England, UK.

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 Bay, Harbour. Dorset

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

Half-Day Guided E-Bike Tour Portland with Brunch

Half-Day Guided E-Bike Tour Portland with Brunch

$176
per adult
Half-Day Guided E-Bike Tour Portland with Brunch
Pauls Walking Tour - Sundays at 10:00am - or Group

Pauls Walking Tours - Sundays at 10:00am

$14
per adult
Pauls Walking Tours - Sundays at 10:00am
See all activities in Upwey

Upwey Hotel Deals

Fairhaven Hotel

Fairhaven Hotel

3 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
$74 nightly
The price is $89 total per night from May 17 to May 18
$89 total
May 17 - May 18
Total with taxes and fees
8.4/10 Very Good! (774 reviews)
Great location .Large comfortable room overlooking beach. Windows old and very draughty ,building a bit tired in places. WiFi non existent in room. Not a hotel problem, but Weymouth car parking charges astronomical!!

Reviewed on May 10, 2026

Fairhaven Hotel
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
$112 nightly
The price is $134 total per night from May 31 to Jun 1
$134 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
We had a brilliant stay in this hotel. The guy who checked us in was really friendly and helpful & the room was bigger than expected. This is our second time staying in this hotel & we will definitely be coming back again next year. The pool is lovely too and pleased children can bring toys with ...

Reviewed on May 16, 2026

Best Western Weymouth Hotel Rembrandt
The Frampton Arms

The Frampton Arms

3.5 out of 5
Station Road Dorchester England
$89 nightly
The price is $107 total per night from May 21 to May 22
$107 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (595 reviews)
Breakfast was well stocked and we had everything we needed

Reviewed on May 15, 2026

The Frampton Arms
See all 2,198 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 $1,570 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.

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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.