Helmsley Vacations from $2,363

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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 $2,548, price is now $2,363 per person
$2,363
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Leeds (LBA)
8.4/10 Very Good! (1,000 reviews)
Looks grand from the outside and reception, with beautiful grounds. It’s dated. Very dated! We booked the cheapest room so walked a few miles in corridors getting lost in lifts that only go to certain rooms and then a stairwell that was really smelly. We had drinks in the bar, asked for coke was given Pepsi without being asked if I was ok with that and then the £4 small bowl of fries was literally cold. No need to return.

Reviewed on May 8, 2026

Leeds Centre by Charles Hope

Leeds Centre by Charles Hope

3 out of 5
Leylands
Price was $2,761, price is now $2,541 per person
$2,541
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Leeds (LBA)
9.4/10 Exceptional! (19 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

Quebecs Luxury Aparthotel

Quebecs Luxury Aparthotel

5 out of 5
Leeds City Center
Price was $2,659, price is now $2,496 per person
$2,496
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Leeds (LBA)
9.6/10 Exceptional! (355 reviews)
Fantastic venue and great location

Reviewed on Apr 17, 2026

262 Apartments

262 Apartments

2 out of 5
Hyde Park
Price was $2,516, price is now $2,364 per person
$2,364
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Leeds (LBA)
8.8/10 Excellent! (5 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

Dakota Leeds

Dakota Leeds

4 out of 5
Leeds City Center
Price was $2,812, price is now $2,645 per person
$2,645
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Leeds (LBA)
9.6/10 Exceptional! (1,005 reviews)
Lovely spacious suite, modern vibe, great location in city

Reviewed on Apr 29, 2026

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Discover the most popular places to visit in Helmsley

Shambles

Shambles

4.5/5(147 reviews)

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

Shambles
York Minster

York Minster

5/5(158 reviews)

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

York Minster
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 lively bars in this family-friendly area.

York Racecourse

What to do in Helmsley

The Yorkshire Dales Tour from York

The Yorkshire Dales Tour from York

$110
per adult
The Yorkshire Dales Tour from York
Boats on river at night

York Evening Escape On The Ouse Cruise

$24
per adult
York Evening Escape On The Ouse Cruise
From York: North Moors and Whitby Tour

From York: North Moors and Whitby Tour

$107
per adult
From York: North Moors and Whitby 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
$166 nightly
The price is $200 total per night from May 14 to May 15
$200 total
May 14 - May 15
Total with taxes and fees
9/10 Wonderful! (414 reviews)
My friend and I had a girlie two night break at this hotel and loved it. When we arrived the receptionist noticed I was using a walking aid and unprompted started looking to change our room to an accessible room eliminating needing to use stairs. We were very touched by his thoughtfulness. It was ...

Reviewed on Apr 21, 2026

Feversham Arms Hotel & Verbena Spa
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 $121 total per night from May 17 to May 18
$121 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (414 reviews)
The staff were friendly and polite. The room was comfy. Location was great overlooking the market square. Breakfast was great, freshly cooked english breakfast plus continental choses. Would definitely stay again.

Reviewed on Apr 30, 2026

The Black Swan - The Inn Collection Group
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
$96 nightly
The price is $115 total per night from May 25 to May 26
$115 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (483 reviews)
All aspects of the food and drinks rooms and bars were very good.

Reviewed on Apr 25, 2026

The Feathers Hotel, Helmsley, North Yorkshire
See all 3,760 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 $2,363 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.