Helmsley Vacations from $1,087

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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.
The Boundary Hotel

The Boundary Hotel

2 out of 5
Headingley
Price was $1,140, price is now $1,087 per person
$1,087
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Leeds (LBA)
6.8/10 (150 reviews)
Value for money hotel. Fixtures and fittings are tired but the bed and bathroom were clean and comfortable. Great value cooked breakfast for £7. Road a bit noisy. We were able to leave our car behind the building for the day which was great. If stairs are an issue/heavy luggage pays to be aware you might have a few flights of steps to climb depending on your room! Staff very helpful and friendly.

Reviewed on Jun 25, 2026

Leeds Centre by Charles Hope

Leeds Centre by Charles Hope

3 out of 5
Leylands
Price was $1,273, price is now $1,205 per person
$1,205
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Leeds (LBA)
9.4/10 Exceptional! (20 reviews)
Fantastic apartment super clean and really plush. Would definitely book again one of the best we've stayed in. Beds were so comfy with quality pillows and duvet. As we couldn't check in till after reception had closed we called the customer service number which is open till 4am. The apartment is called Charles Hope but accessed through new York apartments over the phone we were guided in and let in electronically through each door. It should be made a little clearer on the booking instructions but do not let this put you off.

Reviewed on May 25, 2026

Wool Merchant Hotel

Wool Merchant Hotel

3 out of 5
Price was $1,156, price is now $1,115 per person
$1,115
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Leeds (LBA)
7.6/10 Good! (549 reviews)
Sadly disappointing, needs updating, rooms dusty and dirty. Wouldn't recommend.

Reviewed on Jul 5, 2026

Clayton Hotel Leeds

Clayton Hotel Leeds

4 out of 5
Holbeck
Price was $1,186, price is now $1,148 per person
$1,148
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Leeds (LBA)
9.2/10 Wonderful! (1,000 reviews)
The room was lovely and clean. The beds were really comfy too. Only thing was that the room was very warm.

Reviewed on Jul 5, 2026

Oulton Hall Hotel, Spa & Golf Resort

Oulton Hall Hotel, Spa & Golf Resort

4 out of 5
Price was $1,296, price is now $1,255 per person
$1,255
per person
Sep 19 - Sep 21
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Leeds (LBA)
8.4/10 Very Good! (1,005 reviews)
Beautiful place with great facilities

Reviewed on Jul 5, 2026

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Stay near popular Helmsley attractions

Helmsley Castle

8.6/10 (12 reviews)
You can find out about the history of Helmsley with a visit to Helmsley Castle. Check out the top-notch restaurants or lively bars in this quaint area.
See properties

What to do in Helmsley

York Evening Escape On The Ouse Cruise

York Evening Escape On The Ouse Cruise

$24
per adult
York Evening Escape On The Ouse Cruise
RHS Garden Harlow Carr Entry Ticket

RHS Garden Harlow Carr Entry Ticket

$18
per adult
100% of travellers recommend
RHS Garden Harlow Carr Entry Ticket
York: "All Creatures Great and Small" Yorkshire Dales Tour

York: "All Creatures Great and Small" Yorkshire Dales Tour

$107
per adult
York: "All Creatures Great and Small" Yorkshire Dales Tour
See all activities in Helmsley

Helmsley Hotel Deals

Feversham Arms Hotel & Verbena Spa

Feversham Arms Hotel & Verbena Spa

4 out of 5
High Street York England
$205 nightly
The price is $246 total per night from Jul 12 to Jul 13
$246 total
Jul 12 - Jul 13
Total with taxes and fees
9/10 Wonderful! (435 reviews)
"We stayed for 5 nights. We moved from a standard room at the front corner of the hotel as it was noisy and claustrophobic. The en suite having been built into the corner of the room , so all the other stuff ie chairs table wardrobe were squeezed in. The poolside suite which we were kindly moved to ..."

Reviewed on Jul 6, 2026

Feversham Arms Hotel & Verbena Spa
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
$108 nightly
The price is $129 total per night from Aug 2 to Aug 3
$129 total
Aug 2 - Aug 3
Total with taxes and fees
9.4/10 Exceptional! (491 reviews)
"We had an excellent stay in the hotel right from our arrival staff were able to help and explain about parking etc. We had an absolutely fantastic room 33 with our own outdoor space to enjoy a drink or a coffee / tea in the morning. Large bed was amazing after our day driving and the beautiful roll ..."

Reviewed on Jun 19, 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
$128 nightly
The price is $154 total per night from Jul 12 to Jul 13
$154 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (423 reviews)
"Clean,good bar and great breakfast"

Reviewed on Jun 27, 2026

The Black Swan - The Inn Collection Group
See all 3,874 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 $1,087 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.