Upwey Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Upwey Holiday
Our pick of the best Upwey Hotel Deals
Fairhaven Hotel
Fairhaven Hotel, 37 Esplanade Weymouth England
NZ$250
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (851 reviews)
"The staff were friendly and helpful and got the shower fixed very quickly. Very clean and tidy plenty of room . Shame that you have paper things walls as could hear guests in the next room arguing and kicking off at 01:30 am and then again at 6am not tour fault about the guests but maybe some consideration ..."
Reviewed on 9 Aug 2026
The Jubilee Hotel East- with Spa Facilities
143-146 The Esplanade Weymouth England
NZ$228
1 Sept - 2 Sept
includes taxes & fees
7.2/10 Good! (490 reviews)
"Staff are very helpful I am elderly and disabled stayed with my 11 year old daughter the staff went above and beyond to help us enjoy our stay the food was really nice from the 3 chimneys and well priced I would recommend the jubilee hotel very highly location is perfect and lots happening on ..."
Reviewed on 8 Aug 2026
Best Western Weymouth Hotel Rembrandt
12-18 Dorchester Road Weymouth England
Fully refundableReserve now, pay when you stay
NZ$245
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Pristine throughout and helpful friendly staff and an excellent breakfast 👌"
Reviewed on 8 Aug 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.
What to do in Upwey
Nordic Walking Tour of Weymouth’s Iconic Landmarks
NZ$23
per adult
Frequently asked questions
How much does an Upwey holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Upwey costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Upwey?
The off-season is the best time to visit Upwey if you're on a budget. Another tip for finding cheap Upwey holiday packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Upwey?
The ideal length for your Upwey holiday depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to hit all the top sights and discover some hidden spots along the way.
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 personalise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?
You can enjoy significant savings on your next Upwey getaway by booking a tailored holiday 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 holiday package to Upwey?
If you've got your Upwey holiday 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.
How to plan a trip to Upwey?
- Pick your dates: What you want to do in Upwey and your favourite season will help you decide when to get away.
- Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Upwey.
- Decide how long to go for: Now that you're up to speed on Upwey, you can figure out the perfect length of your break. Create a draft plan and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customised Upwey holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
