Upwey Vacations from $1,093

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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.
Kensington Court Hotel

Kensington Court Hotel

3 out of 5
London City Centre
Save 100% on your flight
Price was $1,618, price is now $1,093 per person
$1,093
per person
Mar 13 - Mar 20
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LHR)
7.6/10 Good! (726 reviews)
The breakfast selection was very good and the staff kept it well stocked and everything cleaned up. The bed was comfy and all was clean. It was nice to have parking, but a little tricky. The staff was so friendly and kind!

Reviewed on Oct 26, 2025

One Bed Serviced Apartment in Chelsea

One Bed Serviced Apartment in Chelsea

3 out of 5
London City Centre
Save 100% on your flight
Price was $2,322, price is now $1,507 per person
$1,507
per person
Mar 13 - Mar 20
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LHR)
6/10 (1 review)
The Knightsbridge Residences

The Knightsbridge Residences

4 out of 5
London City Centre
Save 100% on your flight
Price was $2,667, price is now $1,747 per person
$1,747
per person
Mar 13 - Mar 20
found 15 hours ago
Roundtrip flight included
New York (NYC) to London (LHR)
6/10 (5 reviews)
Needs a refresh. Staff was very friendly and helpful. Of course it was on the less expensive side for similar properties

Reviewed on Jun 20, 2025

Dorsett Canary Wharf London

Dorsett Canary Wharf London

4 out of 5
Canary Wharf
Save 100% on your flight
Price was $1,819, price is now $1,194 per person
$1,194
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.2/10 Wonderful! (19 reviews)
Very nice hotel, staf

Reviewed on Dec 11, 2025

The Hans Residences

The Hans Residences

4 out of 5
London City Centre
Save 100% on your flight
Price was $2,122, price is now $1,421 per person
$1,421
per person
Mar 13 - Mar 20
found 15 hours ago
Roundtrip flight included
New York (NYC) to London (LHR)
6/10 (1 review)
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Discover the most popular places to visit in Upwey

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 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

Pauls Walking Tour - Sat & Sundays at 10:00am - or Group book on 07851934735

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

$13
per adult
Pauls Walking Tour - Sundays at 10:00am - or Group
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
$91 nightly
The price is $109 total per night from Jan 4 to Jan 5
$109 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
The room was nicely appointed and clean, staff were helpful and friendly. Would stay there again.

Reviewed on Dec 20, 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
$70 nightly
The price is $84 total per night from Jan 2 to Jan 3
$84 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.2/10 Very Good! (723 reviews)
All aspects of the room was clean and presentable. Plus we had a fantastic view across the bay. We only seen the reception staff who were both informative and helpful,

Reviewed on Dec 6, 2025

Fairhaven Hotel
The Duchess of Cornwall Inn

The Duchess of Cornwall Inn

3.5 out of 5
12 Queen Mother Square, Dorchester England
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $89 total per night from Jan 18 to Jan 19
$89 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
9.2/10 Wonderful! (136 reviews)
Lovely charming room. Friendly staff. Breakfast/food is great. Would recommend.

Reviewed on Dec 13, 2025

The Duchess of Cornwall Inn
See all 2,129 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 $1,093 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.