Helmsley Vacations from $1,262

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Your Helmsley Vacation

Lock in a Helmsley vacation package that has everything you need and no unnecessary extras. Great for adventure sports, watersports and families, consider basing yourself in the neighborhood of Kirby Misperton. Rievaulx Abbey, Ampleforth Abbey and Byland Abbey are just a few of the many attractions worth checking out during your trip to Helmsley. Browse Expedia's extensive range of travel options and start planning your perfect vacation to Helmsley today.

The Latest Helmsley vacation packages

Price found within the past 48 hours. Click for updated prices.
Oulton Hall Hotel, Spa & Golf Resort

Oulton Hall Hotel, Spa & Golf Resort

4 out of 5
Price was $1,311, price is now $1,262 per person
$1,262
per person
Apr 1 - Apr 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Leeds (LBA)
8.4/10 Very Good! (1,004 reviews)
The room was spacious and large enough to accommadate 2 double beds. Instead it had a double which was 2 large singles pushed together and a pull out bed which was so uncomfortable it couldnt be slept in. We all slept in one bed. No dressing gowns were in the room. The bar meals were expensive and were standard if not poor. The staff were polite

Reviewed on Jan 26, 2026

Leeds Centre by Charles Hope

Leeds Centre by Charles Hope

3 out of 5
Leylands
Price was $1,370, price is now $1,274 per person
$1,274
per person
Apr 1 - Apr 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Leeds (LBA)
9.8/10 Exceptional! (16 reviews)
The need to have ID for every adult in the flat for "health and safety" reasons is ridiculous. The flat itself was very nice though.

Reviewed on Oct 14, 2025

Jorvik House

Jorvik House

4.5 out of 5
Bootham
Price was $1,388, price is now $1,330 per person
$1,330
per person
Apr 1 - Apr 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Leeds (LBA)
9.2/10 Wonderful! (371 reviews)
Lovely comfortable room, incredibly well stocked mini bar including full size bottles of wine. Excellent location, short walk to centre and very quiet.

Reviewed on Jan 29, 2026

262 Apartments

262 Apartments

2 out of 5
Hyde Park
Price was $1,388, price is now $1,331 per person
$1,331
per person
Apr 1 - Apr 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Leeds (LBA)
No reviews
Greeted by a pleasant stain member. Flat was clean. Secure parking is a plus. Things could be improved if they had the following, welcome pack giving WiFi details etc, better equipped kitchen I.e tea towel, bin and more crockery, bathroom could do with bath mat and bedroom could do with bedside cabinet with bedside lamp

Reviewed on Feb 4, 2026

Quebecs Luxury Aparthotel

Quebecs Luxury Aparthotel

5 out of 5
Leeds City Center
Price was $1,372, price is now $1,317 per person
$1,317
per person
Apr 1 - Apr 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Leeds (LBA)
9.6/10 Exceptional! (333 reviews)
As you expect, excellent

Reviewed on Feb 3, 2026

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Discover the most popular places to visit in Helmsley

Shambles which includes street scenes and heritage architecture

Shambles

4.5/5(146 reviews)

This picturesque cobblestone street has a fascinating medieval history and crooked buildings that appear to almost fall into one another.

Shambles
York Minster featuring religious aspects, a church or cathedral and a square or plaza

York Minster

5/5(156 reviews)

The city’s emblem is known for its superb stained-glass windows, underground treasure chambers and tall tower with spectacular views.

York Minster
a little night time photo shot at York Racecourse

York Racecourse

5/5(4 reviews)

You can take time to visit York Racecourse during your travels to York. Check out the shops and top-notch restaurants in this romantic area.

York Racecourse

What to do in Helmsley

Forbidden Chronicles- Tour of York

York's Forbidden Chronicles- Terrors from the dark side.

$17
per adult
York's Forbidden Chronicles- Terrors from the dark side.
York’s Haunted Heart : Ghost, Ghouls and Gallows

York’s Haunted Heart : Ghost, Ghouls and Gallows

$16
per adult
York’s Haunted Heart : Ghost, Ghouls and Gallows
The beautiful city of York has the best preserved medieval streets in the country.

Romans, Vikings and Medieval York: An Audio Tour

$12
per adult
88% of travellers recommend
Romans, Vikings and Medieval York: An Audio Tour
See all activities in Helmsley

Helmsley Hotel Deals

The Feathers Hotel, Helmsley, North Yorkshire

The Feathers Hotel, Helmsley, North Yorkshire

4 out of 5
Market Place York England
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $102 total per night from Mar 8 to Mar 9
$102 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (458 reviews)
Room was very clean, bathroom was small but absolutely fine.

Reviewed on Jan 25, 2026

The Feathers Hotel, Helmsley, North Yorkshire
The Black Swan - The Inn Collection Group

The Black Swan - The Inn Collection Group

4 out of 5
Market Place York England
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $120 total per night from Feb 13 to Feb 14
$120 total
Feb 13 - Feb 14
Total with taxes and fees
8.6/10 Excellent! (401 reviews)
Enjoyed the whole experience

Reviewed on Jan 18, 2026

The Black Swan - The Inn Collection Group
The Royal Oak Hotel

The Royal Oak Hotel

3 out of 5
15 Market Place York England
$89 nightly
The price is $107 total per night from Feb 9 to Feb 10
$107 total
Feb 9 - Feb 10
Total with taxes and fees
8/10 Very Good! (90 reviews)
The room was clean and pleasant, although the toilet was leaking. The noise from the bar music was very loud up until midnight. Easy walking to the venue we were going to so it served it’s purpose at a good price.

Reviewed on Jan 18, 2026

The Royal Oak Hotel
See all 3,523 properties in Helmsley
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 Helmsley Vacation Packages

Helmsley Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Teesside Intl. Airport (MME)
Population
1,500
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Castle Howard, Helmsley Castle and Ryedale Folk Museum

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Frequently asked questions

How much does a Helmsley vacation package cost?
Offering great value package deals from $1,262 on Expedia, you'll be thrilled with how little a vacation to Helmsley costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Helmsley?
March, July and November are the best times to search for cheap Helmsley vacation packages. Traveling in less busy months means you can typically find better prices on flights and hotels.
How many days is enough for Helmsley?
With a well-organized travel plan, you can easily visit the main Helmsley sights in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Helmsley vacation for longer.
Is it worth booking a vacation package to Helmsley?
Helmsley is a good vacation destination with attractions like Hemsley Walled Garden among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Helmsley vacation promises a good time for everyone.
How to find the best Helmsley package deals?
Finding a cheap Helmsley package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Helmsley package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Helmsley vacation as a package?
You can enjoy significant savings on your Helmsley break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Helmsley?
If you're planning an impromptu Helmsley trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Helmsley?

  1. Pick your dates: The things you'd like to do in Helmsley and your preferred season will help you decide when to go.
  2. Budget wisely: Besides the price of your accommodations, you'll need to consider other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Helmsley.
  3. Use Expedia's trip planning tool to explore Helmsley: Research every part of your trip to Helmsley with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide your trip length: Think about how much time you want to spend exploring Helmsley. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Helmsley vacation package.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to do and see. Browse some of the top things to do in Helmsley and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Helmsley vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Helmsley break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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.