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Helmsley Vacations

Pack those stellar shades. We have Helmsley vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Helmsley – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Helmsley vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Helmsley

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Helmsley vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Helmsley well.

Top Hotel Deals

See all 145 Hotels in Helmsley
The Black Swan Hotel

The Black Swan Hotel

Market Place, York
4.5 out of 5.0

Located in Helmsley, this hotel is within a 5-minute walk of Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also within ...

Feversham Arms Hotel & Verbena Spa

Feversham Arms Hotel & Verbena Spa

High Street, York
4.5 out of 5.0

Located in Helmsley, this spa hotel is within a 5-minute walk of Helmsley Castle, Duncombe Park, and Helmsley Arts Centre. Hemsley Walled Garden and Rievaulx ...

The Royal Oak Hotel

The Royal Oak Hotel

15 Market Place, York
3.5 out of 5.0

Located in Helmsley, this inn is steps from Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also within 10 minutes.

The Feathers Hotel

The Feathers Hotel

Market Place, York
4.0 out of 5.0

Located in Helmsley, this inn is steps from Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also within 10 minutes.

Helmsley Garden Cottage & Railway Carriage

Helmsley Garden Cottage & Railway Carriage

1 Bondgate, York
3.5 out of 5.0

This cottage is located in York (Helmsley), close to Helmsley Arts Centre, Duncombe Park, and Helmsley Castle. Local attractions also include Hemsley Walled ...

YHA Helmsley - Hostel

YHA Helmsley - Hostel

Carlton Lane, York
4.5 out of 5.0

Located in Helmsley, this hostel is within a 10-minute walk of Helmsley Arts Centre, Helmsley Castle, and Duncombe Park. Hemsley Walled Garden is 0.6 mi (1 km) ...

Mercure York Fairfield Manor Hotel

Mercure York Fairfield Manor Hotel

Shipton Road, York
4.0 out of 5.0

Located in Skelton, this hotel is 2.4 mi (3.9 km) from Homestead Park and 3 mi (4.9 km) from York Minster. Bootham Bar and York Art Gallery are also within 3 ...

$74

$74
Holiday Inn Express York

Holiday Inn Express York

Malton Road, York
3.0 out of 5.0

Situated in York, this hotel is 0.5 mi (0.8 km) from York Waterworld and within 3 mi (5 km) of York Minster and Shambles. Merchant Adventurers' Hall and Jorvik ...

$128

$128
Aldwark Manor Golf & Spa Hotel

Aldwark Manor Golf & Spa Hotel

Aldwark, York
4.5 out of 5.0

Located in Aldwark, this spa hotel is within 12 mi (20 km) of Allerton Castle, Newby Hall and Gardens, and Homestead Park. York Minster and Shambles are also ...

$149

$149
Best Western Burn Hall Hotel

Best Western Burn Hall Hotel

Tollerton Road, York
3.5 out of 5.0

Situated in a rural location, this hotel is 0.8 mi (1.3 km) from Redwood Park Fishing Lakes and within 12 mi (20 km) of Beningbrough Hall and Garden and York ...

$57

$57