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

3 Star Hotels in Helmsley

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3 Star Hotels in Helmsley

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

Two dogs sitting in front of a fireplace in a rustic room with a stone wall, a wooden table, and a chair.

A staircase with white balusters, a chandelier, a bookshelf, and a window with a view of a tower.

A traditional dining room with wooden tables and chairs, a patterned carpet, and a fireplace.

1. The Royal Oak Hotel

York

$89

$107 total

includes taxes & fees

Oct 26 - Oct 27

A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

A room with two beds, a wooden door, a radiator, and a wall with a floral pattern.

A kitchen with a stainless steel sink, a yellow kettle, and various potted plants on the windowsill.

A staircase with wooden steps and white railings, leading to a landing with a vase of flowers.

2. Cliff House

York

$573

$688 total

includes taxes & fees

Nov 5 - Nov 6

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

A cozy living room with a fireplace, a sofa set, and a wooden door.

A small brick house with a tiled roof, a door, and a window. There is a garden with various plants and flowers in front of the house.

A garden with a pathway leading to a stone house with a tiled roof.

3. 29 Bondgate

York

$559

$671 total

includes taxes & fees

Oct 30 - Oct 31

A building with a sign reading "EN SUITE ACCOMMODATION" and flower baskets on the wall.

A stone building with outdoor seating, a signboard, and parked cars.

A traditional inn with wooden furniture, a patterned carpet, and string lights.

A neatly made bed with a white comforter, multiple pillows, a dark striped throw blanket, a bedside table with a lamp, and a remote control on the bed.

4. The Royal Oak Inn

York

$124

$149 total

includes taxes & fees

Nov 15 - Nov 16

A rural landscape with a stone wall, a road, and neatly trimmed hedges.

A garden with purple flowers and green foliage.

A traditional stone building with multiple windows, surrounded by a well-maintained lawn and various plants.

A table with a vase of purple flowers, salt and pepper shakers, a small bowl, and a teapot.

5. Newburgh House Bed & Breakfast

York

$106

$127 total

includes taxes & fees

Oct 26 - Oct 27

A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a bookshelf.

A traditional stone building with a sign reading "Kings Head Hotel."

A rustic kitchen with a wooden bench and a herringbone-patterned floor.

A bedroom with a large bed, bedside tables, a dresser, a mirror, and a chandelier.

6. Kings Head Hotel

York

$109

$131 total

includes taxes & fees

Nov 1 - Nov 2

A restaurant with a glass ceiling, tables set for dining, and various bottles and decorative items on the tables.

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

A building with ivy-covered walls and a sign for "The Pheasant Hotel."

7. The Pheasant Hotel

York

$260

$312 total

includes taxes & fees

Nov 15 - Nov 16

A bar with various beer glasses and taps, including brands like Black Sheep, Theakston, and John Smith's Extra Smooth.

A cozy dining area with a fireplace, a table set for two, and a bottle of wine.

A cozy room with a stone wall, a wood-burning stove, a bookshelf with wine bottles, and a decorative metal bucket.

A cozy dining area with a brick wall, a wood-burning stove, and a table set for two with pink upholstered chairs.

8. The Oak Tree Inn

York

$77

$93 total

includes taxes & fees

Nov 1 - Nov 2

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

A welcome sign with the name 'The Cove' and 'ION' partially visible, surrounded by greenery.

A bar area with multiple beer taps, a computer monitor, and a sign indicating a 'Food Allergy' policy.

An outdoor patio with wicker furniture, stone flooring, and brick buildings in the background.

9. The Union Inn & Restaurant

Malton

$117

$140 total

includes taxes & fees

Oct 28 - Oct 29

A bedroom with a floral wallpaper, a wooden headboard, and a bed with matching bedding.

A small bathroom with a shower, a white curtain with shell patterns, and a tiled floor.

A bathroom with a white sink, a toilet, and a mirror with a geometric frame.

A two-story building with a sign reading 'Old Red House.'

10. Old Red House Thirskl

Thirsk

$45

$54 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with a table set for four, surrounded by wooden chairs, with a view of a garden through large glass doors.

A stone building with a patio area featuring wooden tables and benches.

A bathroom with a white sink, a glass shower enclosure, and a towel rack.

A grassy area with a small bush of tall, light-colored flowers, a few trees, and a large log on the ground.

11. Cottage Lea's Country Hotel & Restaurant

Pickering

$137

$165 total

includes taxes & fees

Oct 26 - Oct 27

A hotel room with a single bed, a bedside table with a lamp, a TV mounted on the wall, a shelf with a kettle and cups, and a framed floral artwork.

A two-story building with a sign reading "Fourways Guest House Thirsty."

A dining area with tables set for four, each with white tableware and a vase of flowers.

A bedroom with two single beds, a nightstand with a lamp, and a window with curtains.

12. Fourways Guest House

Thirsk

$139

$167 total

includes taxes & fees

Oct 30 - Oct 31

A neatly arranged bedroom with a large bed, a bedside lamp, and a window with a view.

A stone building with multiple windows, a gravel driveway, and outdoor seating.

A stone building with a traditional design, featuring multiple windows and a paved entrance area.

A stone fireplace with a metal grate, a lit fire, and a shelf above holding several metal cups.

13. White Horse Farm Inn

Pickering

$99

$119 total

includes taxes & fees

Oct 30 - Oct 31

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

A bathroom with marble walls, a glass shower enclosure, and two pendant lights.

A bedroom with a bed, bedside tables, a chair, a dresser, and a mirror.

A brick house with a swimming pool, outdoor furniture, and a wooden fence.

14. Dewars Restaurant & Rooms

Kirby Misperton

$228

$274 total

includes taxes & fees

Oct 26 - Oct 27

A bar with a wooden sign reading "THE CROWN".

A compact kitchen with a sink, cabinets, and a window overlooking a parking area.

A neatly arranged hotel room with a bed, a wooden nightstand with a teapot, a chair, and a wall with a tree mural.

A compact kitchen with a sink, stove, and a window with a striped valance.

15. The Crown - Hutton le Hole

York

$134

$160 total

includes taxes & fees

Oct 28 - Oct 29

A building with large windows, a patio area with outdoor seating, and two illuminated trees.

A two-story stone building with a sign reading "Forest & Vale Hotel".

A living room with a fireplace, two upholstered chairs, and a large painting on the wall.

A well-maintained garden with a lawn, a wooden bench, and a house with a stone facade and multiple windows.

16. Best Western Forest & Vale Hotel

Pickering

$160

$193 total

includes taxes & fees

Oct 29 - Oct 30

A restaurant interior with wooden beams, green upholstered seating, and vibrant pink flowers.

A modern staircase with a glass railing and a wooden finish, leading to an upper level.

A hotel with a stone facade, large illuminated letters 'W' and 'S', and a parking lot in front.

A modern fireplace with a circular glass front, set in a marble surround, and a contemporary abstract painting above it.

17. Wainstones Hotel

Middlesbrough

$121

$146 total

includes taxes & fees

Oct 26 - Oct 27

A rooftop pool area with glass railings, outdoor seating, and a view of a road and trees.

A breakfast table set with plates of food, a pitcher, a cup, and a vase with flowers.

A bar area with a variety of liquor bottles, a television screen, and bar stools.

A reception area with a wooden reception desk, a leather chair, a small table with a magazine, and a glass door leading outside.

18. Burn Hall Hotel

York

$60

$72 total

includes taxes & fees

Nov 15 - Nov 16

A tranquil lake with a clear reflection, surrounded by dense forest and a distant hill.

A rustic bar area with a wooden counter, a brick wall, and a hanging light fixture.

A window with a view of a tree and a grassy field.

A rustic stone building with a signpost indicating 'Coast to Coast'.

19. Park House Country Guest House

Northallerton

$119

$119 total

includes taxes & fees

Oct 27 - Oct 28

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

A building with a large glass facade, a wooden exterior, and a landscaped garden with purple flowers.

A restaurant with wooden beams, circular ceiling lights, and a mix of booths and tables.

A reception area with a wooden reception desk, a large leather sofa, and two grey armchairs.

20. Sandburn Hall Hotel

York

$127

$152 total

includes taxes & fees

Nov 1 - Nov 2

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Top landmarks in Helmsley

Helmsley Castle

8.6/10 (12 reviews)

Helmsley Castle is just one of the landmarks located 0.4 mi (0.7 km) from central Helmsley, so you might want to stop by for a few pics during your trip.

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Hemsley Walled Garden

9.0/10 (6 reviews)

Hemsley Walled Garden is 0.5 mi (0.7 km) from central Helmsley, why not stop by during your stay. Want to stretch your legs some more? Head to Duncombe Park, just a short walk away.

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Duncombe Park

8.8/10 (8 reviews)

If you're planning a bit of sightseeing during your trip, head to Duncombe Park— just one of the monuments in central Helmsley.

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Cleveland Way

9.6/10 (10 reviews)

Cleveland Way is 0.4 mi (0.6 km) from central Helmsley, why not stop by during your stay.

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Helmsley Arts Centre

8.0/10 (6 reviews)

If you’re after a show while in the center of Helmsley, you might want to get tickets at Helmsley Arts Centre. If you'd also like to explore some of the parks in Helmsley, Hemsley Walled Garden and Duncombe Park are both a short walk away.

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