Helmsley Vacation Packages 2026 from $1,145

Helmsley flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Boundary Hotel

Headingley

$1,145

per person

Nov 4 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Leeds (LBA)

A bar/lounge and dry cleaning are featured at this hotel, along with free self parking. WiFi in public areas is free. Luggage storage, laundry facilities, and free newspapers are also on offer.

White Rose Hotel & Restaurant - Leeds

Harehills Corner

$1,161

per person

Nov 4 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Leeds (LBA)

This hotel features a restaurant and free self parking. WiFi in public areas is free. Luggage storage is also provided.

Hyatt House Leeds Aparthotel

Leeds City Center

$1,274

per person

Nov 3 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Leeds (LBA)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A coffee shop, dry cleaning, and luggage storage are also on offer.

The Butlers Hotel

Headingley

$1,163

per person

Nov 4 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Leeds (LBA)

A bar/lounge and a snack bar/deli are featured at this hotel, along with free self parking. WiFi in public areas is free. A library, express check-out, and dry cleaning are also on offer.

Best Western Plus Milford Hotel

$1,156

per person

Nov 4 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Leeds (LBA)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Self parking, a coffee shop, and a terrace are also offered.

Top Helmsley hotels deals

The Feathers Hotel, Helmsley, North Yorkshire

Market Place York England

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$153 total

Oct 15 - Oct 16

Total with taxes and fees

This smoke-free inn features 2 restaurants and 2 bars/lounges. WiFi in public areas is free. A terrace, a garden, and dry cleaning are also on offer.

Feversham Arms Hotel & Verbena Spa

High Street York England

Get rates

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free valet parking. Enjoy the hot tub and free perks like English breakfast and free self parking.

The Black Swan - The Inn Collection Group

Market Place York England

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$119 total

Oct 15 - Oct 16

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

The Royal Oak Hotel

15 Market Place York England

$89 nightly

$107 total

Sep 22 - Sep 23

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. WiFi in public areas is free. A coffee shop, a library, and a picnic area are also on offer.

Burn Hall Hotel

Tollerton Road York England

Free Cancellation

Reserve now, pay when you stay

$53 nightly

$64 total

Oct 20 - Oct 21

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Moxy York

Black Horse Lane York England

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$104 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, a snack bar/deli, and a picnic area are also on offer.

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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.

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 lively bars or top-notch restaurants in this relaxing area.

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Frequently asked questions

How much are vacation packages to Helmsley?

Your vacation dreams can all come true in Helmsley from just $1,145. Our affordable package deals include flights and hotels, and they'll make your booking nice and easy. The only thing you'll have to focus on is getting out there and having a great time.

How long should my Helmsley vacation be?

Your Helmsley getaway can be as short or as long as you like, but the majority of travelers stay about 2 nights. Hoping to hop off the beaten path and uncover some lesser-known attractions? Lock in a couple of extra nights and experience a different side of this destination.

Where can I get the best vacation package deals for Helmsley?

You can lock in awesome Helmsley package deals with Travelocity. Pick and choose from 400 air carriers and 1,000,000 properties worldwide and turn those vacation dreams into reality.

Why should I book my Helmsley vacation package via Travelocity?

We've got 24/7 customer support, high-quality service and a Price Match Guarantee. Life's a great big journey — and we have amazing destinations for you to journey to in every nook and cranny of the globe. Travel with us and your bank balance will thank you for it.

Can I save money on my Helmsley car rental if I combine it with hotels and flights?

With a Helmsley vacation package, you can combine your flight, hotel and car bookings and save tons. If you'd love to discover the best of this fabulous destination, why not start with Old Trafford? This famous attraction is 75 mi from Helmsley. With your own wheels, you'll be there in no time.

Which airport is best for Helmsley?

Newcastle Intl. Airport (NCL) is one of the most popular airports in Helmsley. You'll find it 60 mi northwest of the buzzing city center. Other options open to you are Leeds Bradford Airport (LBA) (35 mi away from central Helmsley) and Teesside Intl. Airport (MME) (25 mi away from central Helmsley).

Where should I stay when visiting Helmsley?

If you're looking for a place to base yourself, check out the 2 Bedroom Cottage Situated in The centre of Helmsley With Off Street Parking. It's the top choice for many visitors.