Helmsley Vacations from $999

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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.
Hotel Indigo York by IHG

Hotel Indigo York by IHG

4 out of 5
City Centre
Price was $1,168, price is now $999 per person
$999
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Leeds (LBA)
9.2/10 Wonderful! (1,230 reviews)
Great location, super friendly staff, comfy and cosy room.

Reviewed on Jan 11, 2026

New Holgate

New Holgate

4 out of 5
Holgate
Price was $1,293, price is now $1,017 per person
$1,017
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Leeds (LBA)
9.4/10 Exceptional! (120 reviews)
Stunning hotel , quite small rooms but still very homely! We was even welcomed with a couple of mince pies! Thoroughly enjoyed our stay here. Easy to get to the center of York. Car park is located to the rear of the hotel . Overall a lovely stay. The only reason for 4 star is because the room was a little on the small side and due to being near the restraunt part we could hear the guests going to breakfast. But having said this we would stay again. Thank you so much.

Reviewed on Dec 29, 2025

The Milner York

The Milner York

4 out of 5
South Bank
Price was $1,268, price is now $1,073 per person
$1,073
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Leeds (LBA)
8.6/10 Excellent! (1,620 reviews)
Great place to stay. Great brekkie, great location and great bars

Reviewed on Jan 13, 2026

Judges Court

Judges Court

5 out of 5
City Centre
Price was $1,214, price is now $1,058 per person
$1,058
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Leeds (LBA)
8.6/10 Excellent! (1,002 reviews)
Friendly staff, very central and perfect for what we needed as a base for seeing York at night.

Reviewed on Dec 25, 2025

DoubleTree by Hilton York

DoubleTree by Hilton York

4 out of 5
The Groves
Price was $1,153, price is now $1,010 per person
$1,010
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Leeds (LBA)
7.8/10 Good! (1,001 reviews)
Hotel dated for a 4 star radiator not working and toilet roll holder hanging off the wall

Reviewed on Jan 19, 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.
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
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
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
$94 nightly
The price is $113 total per night from Jan 21 to Jan 22
$113 total
Jan 21 - Jan 22
Total with taxes and fees
9.2/10 Wonderful! (453 reviews)
Super room and fabulous meals.

Reviewed on Jan 15, 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 $119 total per night from Jan 26 to Jan 27
$119 total
Jan 26 - Jan 27
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 Jan 21 to Jan 22
$107 total
Jan 21 - Jan 22
Total with taxes and fees
8/10 Very Good! (89 reviews)
The location, facilities and PEOPLE make this a superb place to stay in North Yorkshire

Reviewed on Jan 4, 2026

The Royal Oak Hotel
See all 3,474 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 $999 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.

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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.