A historic castle ruin with two towers on a grassy hill.

Search Holiday Rentals in Helmsley

Q: What are some of the best holiday rentals that Helmsley has to offer?

Vas's York House : This holiday home rental outside of Helmsley is equipped with a garden, daily housekeeping and free WiFi to help you feel comfortable during your stay.

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Helmsley holiday rentals

A cozy living room with a fireplace, a television, and comfortable seating.

1. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Helmsley

Helen H.

includes taxes & fees

7 Nov - 8 Nov

A bedroom with a bed, a window with a view, a wardrobe with louvered doors, and a hanging light fixture.

2. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY

includes taxes & fees

24 Nov - 25 Nov

A dining area with a wooden table set for four, surrounded by chairs. A vase with flowers is on the table, and there is a fireplace with a mantel to the left.

3. Cliff House

York

includes taxes & fees

18 Nov - 19 Nov

A bathroom with a window, a sink, a mirror, a vase with flowers, and a towel rack.

4. Eighteen Pottergate - Beautiful cottage with garden central location

HELMSLEY

includes taxes & fees

7 Nov - 8 Nov

A stone building with a patio area featuring a table and chairs.

5. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Helmsley

includes taxes & fees

15 Nov - 16 Nov

A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

6. 29 Bondgate

York

includes taxes & fees

10 Nov - 11 Nov

A compact kitchen with a washing machine, a sink, and a stove.

7. Lilac Cottage

York

Kevin

includes taxes & fees

14 Nov - 15 Nov

A glass on a hot tub with a view of a green field and mountains in the background.

8. Cosy Rural Cabin with Private Hot Tub

Thirsk

Alex

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

9. Keldholme Cottage 1 - UK10992

Keldholme, near Kirkbymoorside

John Kelly

includes taxes & fees

17 Nov - 18 Nov

A patio with a table and chairs, surrounded by lush greenery and a wooden fence.

10. 1 bedroom accommodation in Slingsby, near Malton

Slingsby, near Malton

Carol Horne

includes taxes & fees

9 Nov - 10 Nov

Two wooden pod-style cabins with large windows and seating areas, surrounded by a well-maintained lawn and trees.

11. Daisy Family Glamping Pod | sleeps 4 - Gold Award winning

Pickering

James E.

includes taxes & fees

8 Nov - 9 Nov

A campsite with two cabins, each with a wooden deck and outdoor seating.

12. The Little Hide - Adult Only Camping Pods

York

Steve

includes taxes & fees

29 Nov - 30 Nov

A compact hotel room with a kitchenette, a dining area, and a bed with a blue headboard.

13. Station Suites

Middlesbrough

Alan

includes taxes & fees

13 Nov - 14 Nov

A cozy wooden cabin with a hot tub, a fire pit, and a dining area.

14. Wigwam Holidays Cabin with Hot Tub and Pergola

Northallerton

includes taxes & fees

8 Nov - 9 Nov

A spacious room with a large sliding glass door leading to an outdoor patio area.

15. Goodramgate Apartments

York

Christian

includes taxes & fees

12 Nov - 13 Nov

A stone building with a steeply pitched roof, a narrow street, and a clear sky.

16. Heather Cottage - a beautiful cosy cottage

Snainton

Luigi

includes taxes & fees

8 Nov - 9 Nov

A two-story stone house with a brick facade, surrounded by a garden with various plants and flowers.

17. Auburn House

York

Stephen

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a brown sofa, a wall-mounted light, and a sliding glass door leading to an outdoor area.

18. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

Pickering

Joy

includes taxes & fees

9 Nov - 10 Nov

A brick building with a sign for 'The Duke Of Wellington COURTYARD ROOMS.' There are picnic tables with umbrellas, a gravel courtyard, and a staircase leading to the entrance.

19. Welbury Studio, Sleeps 2, Pet Friendly & Parking

Northallerton

Gillian

includes taxes & fees

23 Nov - 24 Nov

A staircase with white balusters, a door with a circular glass window, and a wall-mounted light fixture.

20. Middlesbrough Lodge

Middlesbrough

Beatrice

includes taxes & fees

19 Nov - 20 Nov

View all properties

Find holiday rentals that suit your style

Top Helmsley Hotel Reviews

A traditional hotel with multiple buildings, including a Tudor-style structure and a stone building with a sign for "The Hotel."

The Black Swan - The Inn Collection Group

York

10/10 Excellent

Les

A stone building with a red-tiled roof, a stone archway, and a garden with yellow flowers.

The Royal Oak Hotel

York

10/10 Excellent

terence

An outdoor patio area with wicker furniture, stone flooring, and a pergola covered in greenery.

The Pheasant Hotel

York

10/10 Excellent

Gorgeous looking hotel. Already lovely but excited to see it when their plans to gain a 4th star come to fruition. My only qualms are rather thin walls to the next bathroom (you can hear the next rooms shower power unit) and the ventilation (weather was low 20s but room got full sun and with no air con it was very hot, even with windows fully open). Otherwise, tasteful decor, a really nice restaurant with super food and a beautiful location.

Rachael

A brick building with a sign reading "Plum Partridge."

Plum and Partridge Inn

York

10/10 Excellent

Mhairi

A dining area with a wooden table set for four, a kitchen with a central island, and a view through a glass door to the outside.

The Carpenters Arms

Thirsk

10/10 Excellent

NICOLA

A covered outdoor seating area with wicker furniture, a ceiling projector, and a view of a green landscape.

Newsham Grange Farm Bed and Breakfast

Thirsk

10/10 Excellent

First off, Sue (the owner) is just the best! I phoned in advance and asked a couple of favours of her, to put a couple of gifts in the room to surprise my girlfriend. Not only did she do it but she did it for less than budget! (If you do ask something of her like this, it's only fair to reward the wonderful lady with a gift of her own. OK?! Haha!) Newsham Grange is gorgeous. We had a fantastic overnight stay and wow that breakfast is good. We were lucky enough to use the pool and outdoor...

Andrew

A stone building with a red-tiled roof, a covered patio area, and a landscaped garden with a paved walkway.

Dewars Restaurant & Rooms

Kirby Misperton

10/10 Excellent

Ashley

A modern hotel room with a large bed, a sitting area with a chair, a view of the outdoors, and a balcony.

Sandburn Hall Hotel

York

10/10 Excellent

Elizabeth

A bedroom with a bed, two wall-mounted paintings, bedside lamps, and a neatly made bed with folded towels.

The Union Inn & Restaurant

Malton

10/10 Excellent

emily

A backyard with a picnic table, a small shed, and a car parked on the street.

Old Oak Tree

Thirsk

10/10 Excellent

Anonymous traveller

A hallway with a checkered floor, a chandelier, a radiator, and a door with a stained glass window.

MonkBridge House

The Groves

10/10 Excellent

John

Find out more about Helmsley

Everything you need to know about Helmsley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Helmsley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Helmsley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Helmsley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Helmsley. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Helmsley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Helmsley holiday rentals we have selected for you start as low as £53 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Helmsley rentals

At Expedia, we put the best Helmsley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Helmsley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Helmsley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Helmsley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Helmsley?

Yes, there are holiday rentals in Helmsley close to Helmsley Arts Centre, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and spas in Helmsley. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Helmsley has to offer?

Vas's York House: This holiday home rental outside of Helmsley is equipped with a garden, daily housekeeping and free WiFi to help you feel comfortable during your stay.

How many holiday rentals will I find in Helmsley?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Helmsley stay.

What can I see and do in Helmsley?

Hemsley Walled Garden and Howardian Hills are a couple of scenic spots to enjoy the outdoors, whereas Helmsley Arts Centre is one of the cultural attractions. Other places in town to visit include Helmsley Castle and North York Moors National Park.

What are holiday rentals like in Helmsley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Helmsley. Holiday rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.

Explore a world of travel with Expedia

Things to do in Thirsk
Standard Link for Things to do in Thirsk

Search Holiday Rentals in Helmsley

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Helmsley holiday rentals

1. Beautiful stone cottage in the heart of Helmsley - sleeps 2

2. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

3. Cliff House

4. Eighteen Pottergate - Beautiful cottage with garden central location

5. Hyland Cottage - sleeps 6 guests in 3 bedrooms

6. 29 Bondgate

7. Lilac Cottage

8. Cosy Rural Cabin with Private Hot Tub

9. Keldholme Cottage 1 - UK10992

10. 1 bedroom accommodation in Slingsby, near Malton

11. Daisy Family Glamping Pod | sleeps 4 - Gold Award winning

12. The Little Hide - Adult Only Camping Pods

13. Station Suites

14. Wigwam Holidays Cabin with Hot Tub and Pergola

15. Goodramgate Apartments

16. Heather Cottage - a beautiful cosy cottage

17. Auburn House

18. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

19. Welbury Studio, Sleeps 2, Pet Friendly & Parking

20. Middlesbrough Lodge

Find holiday rentals that suit your style

Top Helmsley Hotel Reviews

The Black Swan - The Inn Collection Group

10/10 Excellent

Find out more about Helmsley

Helmsley holiday rentals: An excellent choice for every season

How to find incredible deals on Helmsley rentals

Frequently Asked Questions

Can I find holiday rentals in Helmsley?

What are some of the best holiday rentals that Helmsley has to offer?

How many holiday rentals will I find in Helmsley?

What can I see and do in Helmsley?

What are holiday rentals like in Helmsley?

Explore a world of travel with Expedia