Helmsley Vacation Rentals & Homes - 314 Rentals Available
314 Vacation rentals
PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture
Nawton House
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
- Pet friendly
$125.00
from $125.00 / night
CASTLE VIEW, pet friendly, character holiday cottage, with a garden in
Helmsley House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$219.00
from $219.00 / night
OAKLEIGH HOUSE, attractive cottage, near walks, attractions and amenities, two
Nawton House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$136.00
from $136.00 / night
BLACK CAT COTTAGE, woodburner, on working farm, superb accommodation, Helmsley
Hawnby House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$137.00
from $137.00 / night
8 POTTERGATE MEWS, terraced, enclosed garden, in Helmsley, Ref 956799
Helmsley House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
$203.00
from $203.00 / night
WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden
Helmsley House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$95.00
from $95.00 / night
SHEPHERD'S HUT, working farm, valley views, near Helmsley
Hawnby Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Pet friendly
$90.00
from $90.00 / night
LITTLE MANOR FARM COTTAGE, romantic, WiFi, character holiday cottage in Nawton
Nawton House
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
$87.00
from $87.00 / night
ORCHARD COTTAGE, character, woodburning stove, in Helmsley, Ref 913657
Helmsley House
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- 3 nights min
- Child friendly
$121.00
from $121.00 / night
CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location
Helmsley House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
$115.00
from $115.00 / night
AUBURN HOUSE, detached, woodburning stove, near Helmsley, ref:943848
Helmsley House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Private garden
$195.00
from $195.00 / night
OSBOURNE COTTAGE, open fire, character, in Helmsley, Ref 914229
Helmsley House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$202.00
from $202.00 / night
44 ELMSLAC ROAD, pet-friendly, spacious interior, conservatory, Ref 971251
Helmsley House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$179.00
from $179.00 / night
IVY COTTAGE, end-terrace, WiFi, lawned garden, close to town centre, in
Helmsley House
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
$135.00
from $135.00 / night
ARCHWAY HOUSE, pet-friendly, peaceful location, four poster bed, two bathrooms
Nawton House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$140.00
from $140.00 / night
BELLWETHER, WiFi, open-plan, near Helmsley
Nawton Yurt
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
$102.00
from $102.00 / night
THE BRYE, pet-friendly, WiFi, near Thirsk
Scawton Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Pet friendly
$112.00
from $112.00 / night
THE COTTAGE, WiFi, open-plan, near Thirsk
Scawton Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Pet friendly
$112.00
from $112.00 / night
Your search has been expanded 19.9 miles to include more rentals
Ryedale Country Lodges - Willow Lodge, Kirkbymoorside
Kirkbymoorside Log cabin - 5.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
$145.00
from $145.00 / night
THE FLOUR POT detached stone cottage, en-suite, WiFi, Pickering, Ref 936971
Pickering House - 10.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
$158.00
from $158.00 / night
PREACHER'S REST, 5 bedrooms, Grosmont Nr Whitby
Grosmont Cottage - 18.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
$198.00
from $198.00 / night
Smiths Cottage, Ampleforth
Grimstone Cottage - 6 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
$129.00
from $129.00 / night
WHEATSHEAF COTTAGE, 8 bedrooms, Whitby
Egton Cottage - 18.5 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
$290.00
from $290.00 / night
THE HOLLIES, detached, all ground floor, gas fire in sitting room, lovely
Pickering House - 11.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$128.00
from $128.00 / night
Sycamore Cottage, Hutton Rudby
Hutton Rudby House - 16.6 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$149.00
from $149.00 / night
Cosy Cottage, Swainby
Swainby House - 14.1 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- 3 nights min
- Child friendly
- Pet friendly
$108.00
from $108.00 / night
MEADOW COTTAGE, on working farm, open-plan, exposed beams, Ref 974387
Kirkbymoorside Cottage - 5.9 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Pet friendly
$113.00
from $113.00 / night
The Barn at Orchard Farm, York
Nun Monkton Cottage - 18 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
$148.00
from $148.00 / night
WHITE ROSE COTTAGE, WIFI, centre of Guisborough, contemporary furnshings, Ref
Guisborough House - 19.9 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$108.00
from $108.00 / night
THE LOFT, WIFI, open plan, king size bed, Ref 961175
Great Ouseburn House - 16.6 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
$92.00
from $92.00 / night
POND VIEW, charming interior, near Thirsk
Ainderby Quernhow Cottage - 15.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
$150.00
from $150.00 / night
THE STABLES, exposed beams, woodburning stove, pet friendly, in Ebberston, Ref
Ebberston House - 17.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
$141.00
from $141.00 / night
Little Pines, Snainton
Ebberston Cottage - 19 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$148.00
from $148.00 / night
Thorn Abby Lodge, Malton
Great Habton Log cabin - 10.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Private garden
$163.00
from $163.00 / night
HAWTHORNE COTTAGE, pub across road, Howardian Hills AONB, en-suite, Ref 974508
Crayke House - 8.9 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$254.00
from $254.00 / night
7 OFFICE ROW, honey pot location, enclosed garden, pet-friendly, in Grosmont
Grosmont Cottage - 18.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$107.00
from $107.00 / night
ST. HEDDAS COTTAGE, stone cottage, woodburning stove, three bedrooms, walks
Egton Bridge House - 17.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$142.00
from $142.00 / night
NEW STABLE COTTAGE, views of Moors, stable conversion, Smart TV, Ref 925536
Lealholm Cottage - 16.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$159.00
from $159.00 / night
THE ARCHES, pet friendly, character holiday cottage, with a garden in Farndale
Church Houses House - 9.7 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$110.00
from $110.00 / night
CROFT HEAD COTTAGE, romantic, character holiday cottage, with open fire in
Pickering House - 9.7 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$95.00
from $95.00 / night
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