Cottages in Helmsley

Within 10 miles
  • Within 1 mile
  • Within 2 miles
  • Within 3 miles
  • Within 5 miles
  • Within 10 miles
  • Within 20 miles
  • Within 30 miles
  • Within 50 miles
1
2
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
Pets
  • Pets
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • Property pet free
7
  • 7
  • 3
  • 4
  • -
  • 2
  • 5
  • 6
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
3 Days +/-
  • Exact Dates
  • 1 Day +/-
  • 2 Days +/-
  • 3 Days +/-
Our most popular properties are filling up fast!

British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Cottages in Helmsley

REFINE SEARCH

Your Helmsley, North Yorkshire search returned 141 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
Map View
A row of brick houses with arched windows and doors with potted plants outside at Chapel Cottage in Stillington near Easingwold and York
33
Stillington near Easingwold and York, North Yorkshire, YO61
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

Attractive, period cottage in pretty Stillington village. Character beams, open fire, enclosed sunny courtyard garden. Quality accommodation, well-equipped and comfortable. Many attractions close by. York 10 miles. (Ref. 28836)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $594

See more details
An outdoor deck with a hot tub wooden deck chairs a table and a grill with trees in the background at Cropton Golden Oak Hideaway in Cropton Forest
23

Holiday Park

Cropton Forest, North York Moors National Park, YO18
  • Sleeps2
  • Bedrooms1
  • PetsNo

(Ref. 1146702)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from $1893

See more details
A stone house with a tiled roof and a green door with plants in pots outside at Owls Nest in Stearsby near Brandsby
Offer
21
Stearsby near Brandsby, North Yorkshire, YO61
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Owl's Nest is a fabulous detached barn conversion offering flexible accommodation and beautifully positioned in the glorious Howardian Hills near York and Malton. York 12 miles. (Ref. 20946)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

  • 5% off - Fri 11th Jul to 24th Jul 2025

7 nights from $771

See more details
A stone cottage with wooden shutters and a small outdoor seating area at Cow Byre Cottage in Wrelton near Pickering
10
Wrelton near Pickering, North Yorkshire, YO18
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Delightful conversion of old cow byre in centre of Wrelton. Exposed timbers, wooden floors. Quality cottage, very high standard. Excellent walking and touring base. Pickering 3 miles. (Ref. 1577)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from $421

See more details
A stone cottage with solar panels on the roof and a gravel courtyard with picnic tables at Kitchen Cottage in Thirsk
15
Thirsk, North Yorkshire, YO7
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

A charming barn conversion located near the village of Thirsk, North Yorkshire. Breakfast bar. Open-plan. High ceilings. Ripon 11 miles; York 23 miles. (Ref. 19934)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from $393

See more details
A wooden cabin with a porch, two chairs, a small table, and a grassy lawn at Rising Sun in Kirkbymoorside
22
Kirkbymoorside, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A lovely one-bedroom lodge perched near Kirkbymoorside, North Yorkshire. Pet-free. Wood fired hot tub. Near National Park. Romantic. Pickering 5.8 miles; Helmsley 7.3 miles. (Ref. 1049218)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Washing machine

7 nights from $672

Last booked 2 days ago
See more details
A stone cottage with red tile roof and white framed windows next to a small gravel area with a wooden fence and surrounded by greenery at Yon Cottage in Stonegrave near Hovingham
22
Stonegrave near Hovingham, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A wonderful, semi-detached cottage settled in Stonegrave near Hovingham, North Yorkshire. Woodburning stove. Near National Park. Romantic. Helmsley 5.9 miles; Malton 10.1 miles; York 18.5 miles. (Ref. 1106690)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from $474

Last booked yesterday
See more details
A wooden shepherds hut with an open door behind a wooden gate and stone wall with chairs and table on grass at Sheep Cote Shepherds Hut in Chop Gate near Stokesley
27
Chop Gate near Stokesley, North York Moors National Park, TS9
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A gorgeous, one-bed hut sitting in a rural location in Chop Gate, near Stokesley, North Yorkshire. Countryside location. Ideal for couples. Rural views. Great Ayton 10.4 miles; Saltburn-by-the-Sea 20.2 miles. (Ref. 1126877)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $737

See more details
A stone exterior wall of a house with a door and windows and potted plants on a paved patio at Mole End in Wass near Helmsley
19
Wass near Helmsley, North York Moors National Park, YO61
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Mole End is a lovely, single-storey cottage located in the charming market town of Helmsley, North Yorkshire. Woodburning stove. Couple's retreat. Kirkbymoorside 13.2 miles; Thirsk 12.8 miles; Pickering 20.3 miles; York 22 miles. (Ref. 1151091)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $486

See more details
A stone cottage with a green front door surrounded by plants and flowers with a patio area at Cartwheel Cottage in Yearsley
19
Yearsley, North Yorkshire, YO61
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A charming ground floor annexe resting in Yearsley, North Yorkshire. Open-plan living. Malton 13.4 miles; York 16 miles. (Ref. 1022390)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher

7 nights from $757

See more details
A gravel path leading to a small building with ivy-covered walls and a tiled roof surrounded by various green bushes and white flowering plants at The Hayloft in Lastingham
19
Lastingham, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

Charming detached stone-built barn conversion in picturesque Lastingham. Quality accommodation with woodburning stove. Excellent walking, coast easily accessible. Pickering 7 miles. (Ref. 1571)

  • Wi-fi
  • Off-road parking

7 nights from $478

Last booked 3 days ago
See more details
An outdoor area with brick walls wooden doors hanging flower baskets and stone paving at Stable Cottage in Sutton-Under-Whitestonecliffe near Thirsk
15
Sutton-Under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A single-storey barn conversion in courtyard setting on the outskirts of the small village of Sutton-Under-Whitestonecliffe. Romantic retreat. Open plan living area. Superb area for walking and touring. Thirsk 4 miles. (Ref. 14936)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from $401

See more details
A brick garage with an outdoor staircase and a seating area with a red umbrella at The Stables Crayke Lodge in Easingwold
18
Easingwold, North Yorkshire, YO61
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Beautiful, first floor, studio-style cottage in rural location. Close to Easingwold and Crayke. Tastefully furnished to high standard. Woodburner, splendid views. Easy access to York. Easingwold 2 miles. (Ref. 917511)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly

7 nights from $424

See more details
An outdoor seating area with a table and two chairs next to a small shed and a covered seating area at Bellwether in Helmsley
24
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A superb, shepherd’s hut situated on the outskirts of the market town of Helmsley. Woodburner. WiFi. Rural views. Kirkbymoorside 3.9 miles; Pickering 10.9 miles. (Ref. 986040)

  • Wi-fi
  • Ground floor bedroom

7 nights from $413

See more details
A wooden cabin with a porch and outdoor seating area with a small table and chairs at Peep o Day in Kirkbymoorside
22
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A beautiful one-bedroom lodge resting on the outskirts of Kirkbymoorside, North Yorkshire. Off-road parking. Near a National Park. Romantic. Pickering 5.8 miles; Helmsley 7.3 miles. (Ref. 1049219)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Washing machine

7 nights from $672

See more details
A wooden cabin with outdoor seating and a covered hot tub on a stone patio at Westfield Lodge in Terrington near Sheriff Hutton
18
Terrington near Sheriff Hutton, North Yorkshire, YO60
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

A charming detached, single-storey lodge settled in Terrington near Sheriff Hutton, North Yorkshire. Hot tub. Parking. Romantic. Malton 9.2 miles; York 13.4 miles. (Ref. 1095905)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub

7 nights from $732

See more details
A stone building with glass patio doors and a glass balustrade beside a gravel area and wooden fence at Shippon in Beadlam
44
Beadlam, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A romantic, single-storey cottage resting in Beadlam, North Yorkshire. Open-plan. Beautiful views. Helmsley 2.2 miles; Pickering 10.9 miles; York 24.4 miles. (Ref. 1099725)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from $559

See more details
A stone cottage with a tiled roof and metal railing in a rural setting at Beckside in Lastingham
18
Lastingham, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Detached stone built stable conversion in pretty Lastingham village. Quality ground floor accommodation, streamside patio. Ideal for York Moors & Coast. Pickering 7 miles. (Ref. 1293)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $489

See more details
A wooden cabin with a deck surrounded by trees in a grassy area at Cropton Silver Birch in Cropton Forest
19

Holiday Park

Cropton Forest, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

(Ref. 1146829)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from $1380

See more details
A stone house with a tiled roof and a small garden with a table and two chairs at 8 Pottergate Mews in Helmsley
27
Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

Ideal for a family holiday in the heart of market town. Front garden and rear courtyard. WiFi. Thirsk 14 miles. (Ref. 956799)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from $794

See more details
Map View

On the border of the North York Moors National Park, this delightful market town is a haven for walkers and lovers of the outdoors.

Why Helmsley?

After an action-packed day among the wonders of the North York Moors, our Helmsley cottages enjoy close proximity to the town's charming pubs and delightful tea rooms to recharge the batteries. There is a selection of excellent independent shops and a weekly market along its attractive streets to pick up some of the finest local produce. From your Helmsley accommodation, be sure to explore the stunning Helmsley Castle and sculpture garden, as well as Duncombe Park and the National Centre for Birds of Prey for nature enthusiasts.

Places to Visit near Helmsley

Our range of cottages in Helmsley rest on the southern fringes of the North York Moors National Park, perfectly based for a break filled with activity and adventure. This National Park hugging the coast of Yorkshire has much to offer, not least its wide range of walks and cycle paths taking in some of the finest landscape scenery imaginable. Discover a handful of unique villages in and around the spectacular moors, waiting to be explored with rustic inns and delightful cafés offering those mid-adventure refreshments. Make your Helmsley cottage holiday a memorable one by visiting popular spots such as Ampleforth, Hutton-le-Hole, Kirkbymoorside, Pickering, Ripon and Thirsk.

Types of Holidays

All types of holidays can be enjoyed across Yorkshire with Sykes, whether you're seeking a Yorkshire cottage by the sea, or more of a rural retreat at a cottage in the Yorkshire countryside. Bring your dog along to enjoy the sublime walking country nearby by booking a North York Moors pet-friendly cottage, or really treat yourselves to a break in a Yorkshire luxury cottage.