Helmsley Vacations from $1,250

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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.
St George's Guest House

St George's Guest House

3.5 out of 5
South Bank
Price was $1,410, price is now $1,250 per person
$1,250
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
Jacksonville (JAX) to Leeds (LBA)
9.2/10 Wonderful! (111 reviews)
Lovely place and will definitely return.

Reviewed on Jul 20, 2025

City Apartments Monkbar Mews

City Apartments Monkbar Mews

4 out of 5
Price was $1,648, price is now $1,476 per person
$1,476
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
Jacksonville (JAX) to Leeds (LBA)
9.2/10 Wonderful! (35 reviews)
Great location Right in the heart of everything Very well presented apartment

Reviewed on Sep 20, 2025

The Milner York

The Milner York

4 out of 5
South Bank
Price was $1,439, price is now $1,316 per person
$1,316
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
Jacksonville (JAX) to Leeds (LBA)
8.6/10 Excellent! (1,531 reviews)
Wonderful hotel, super easy from the train station - there is an entrance in the station. Really lovely room with a great bathroom and friendly staff.

Reviewed on Sep 21, 2025

Hotel du Vin & Bistro York

Hotel du Vin & Bistro York

4 out of 5
South Bank
Price was $1,462, price is now $1,362 per person
$1,362
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
Jacksonville (JAX) to Leeds (LBA)
9.2/10 Wonderful! (1,005 reviews)
Warm welcome, great base for visiting the city.

Reviewed on Sep 16, 2025

The Churchill Hotel

The Churchill Hotel

4 out of 5
Clifton
Price was $1,557, price is now $1,463 per person
$1,463
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
Jacksonville (JAX) to Leeds (LBA)
9/10 Wonderful! (1,002 reviews)
We loved our stay at the Churchill. It’s in a great location, about a 10 minute walk from York centre. The hotel was very clean and nicely decorated. The food in the bar was great-big portions too. Staff were lovely, friendly and helpful. Overall this hotel is wonderful and we would definitely stay here again!

Reviewed on Sep 14, 2025

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Discover the most popular places to visit in Helmsley

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
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
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 lively bars in this family-friendly area.

York Racecourse

What to do in Helmsley

York Hop-On Hop-Off Bus Tour

City Sightseeing York Hop-On Hop-Off Bus Tour

$23
per adult
90% of travellers recommend
City Sightseeing York Hop-On Hop-Off Bus Tour
From York: North Moors and Whitby Tour

From York: North Moors and Whitby Tour

$94
per adult
100% of travellers recommend
From York: North Moors and Whitby Tour
York's Chocolate Story: Guided Tour

York's Chocolate Story: Guided Tour

$29
per adult
100% of travellers recommend
York's Chocolate Story: Guided 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, Helmsley, York, England
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $134 total per night from Sep 28 to Sep 29
$134 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (431 reviews)
"Very nice place, staff are really friendly and helpful."

Reviewed on Sep 13, 2025

The Feathers Hotel, Helmsley, North Yorkshire
Feversham Arms Hotel & Verbena Spa

Feversham Arms Hotel & Verbena Spa

4 out of 5
High Street, Helmsley, York, England
$188 nightly
The price is $226 total per night from Oct 12 to Oct 13
$226 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (392 reviews)
Fantastic place
"Brilliant hotel, only stayed one night and couldn't use the spa, but room was great as was breakfast staff so friendly"

Reviewed on Sep 17, 2025

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, Helmsley, York, England
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $120 total per night from Sep 28 to Sep 29
$120 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (376 reviews)
Top Job - no complaints
"We had a big room which fitted us nicely. Check in was efficient and easy. Food and drink both good ( we ate in one night) staff were all friendly and helpful, no complaints at all!"

Reviewed on Sep 14, 2025

The Black Swan - The Inn Collection Group
See all 1,665 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.

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Frequently asked questions

How much does a Helmsley vacation package cost?
Offering great value package deals from $1,250 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

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.