Glaisdale Holiday Cottages

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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.

Glaisdale Holiday Cottages

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Your Glaisdale, North Yorkshire search returned 600 cottages

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Map View
Stone terraced houses with green door and small front garden at Pheasant Cottage in Danby
17
Danby, North York Moors National Park, YO21
  • Sleeps2
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A characterful, stone-built cottage resting near the village of Danby. Woodburning stove. WiFi. Pub within 0.2 miles. Whitby 16.5 miles. (Ref. 1007774)

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

7 nights from £350

Last booked yesterday
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A stone house with chimneys and windows surrounded by trees and a grassy area at Westonby Lodge in Shortwaite near Lealholm
25
Shortwaite near Lealholm, North York Moors National Park, YO21
  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A large, detached former hunting lodge, surrounded by panoramic countryside views, in Shortwaite near Lealholm, in the North York Moors National Park. Incredible views. Woodburning stove. Large, enclosed garden. Whitby 8.1 miles; Scarborough 26.1 miles. (Ref. 1026625)

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

7 nights from £633

Last booked yesterday
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The exterior of a stone cottage with two white front doors a black metal gate and wooden bench at Hart Cottage in Glaisdale
31
Glaisdale, North York Moors National Park, YO21
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A charming, stone terraced cottage in the heart of Glaisdale. Character beams, stripped doors, woodburner. Glorious views over open countryside. Whitby 8 miles. (Ref. 1015513)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £365

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A stone building with green doors and white windows with a wooden fence and grass in front at Manor House Farm Cottage in Roxby near Staithes
23
Roxby near Staithes, North York Moors National Park, TS13
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A splendid two-bedroom cottage resting on a working farm in Roxby near Staithes in North Yorkshire. Country views. Close to amenities. Original features. Saltburn-by-the-Sea 10.9 miles; Whitby 12 miles; Middlesbrough 22.2 miles (Ref. 1084493)

  • Wi-fi
  • Off-road parking

7 nights from £369

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Exterior view of a stone and wood sided building with windows and a paved patio at The Old Jet Workshop in Whitby
New property
36
Whitby, North Yorkshire, YO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Old Jet Workshop is a harmonious single-storey cottage in the heart of Whitby, North Yorkshire, boasting an open-plan layout and is near the beach. Robin Hood's Bay 6.2 miles; Scarborough 20.3 miles; Pickering 21.2 miles; Guisborough 22 miles. (Ref. 1173443)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £369

Last booked yesterday
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A stone barn with red tile roof and blue doors next to a gravel path and green lawn at Basils Barn in Egton near Grosmont
26
Egton near Grosmont, North York Moors National Park, YO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A quirky barn conversion situated in Egton Bridge near Grosmont, on the edge of the North York Moors National Park. Woodburning stove. Romantic dwelling. Lawned garden. Whitby 6.8 miles; Pickering 18.5 miles. (Ref. 1064996)

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

7 nights from £416

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A railway platform with train tracks and a long stone building with multiple windows at Duchess of Hamilton @ Engine Shed in Whitby
New property
30
Whitby, North Yorkshire, YO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Duchess of Hamilton is a beautiful, ground-floor apartment resting in the popular seaside town of Whitby in North Yorkshire near the local beach. Robin Hood's Bay 5.7 miles; Pickering 20.7 miles; Guisborough 21.6 miles. (Ref. 1172078)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £582

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A single-story building with a brick section and green wooden siding surrounded by trees and grass at Bee Garth in Castleton near Danby
32
Castleton near Danby, North York Moors National Park, YO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This delightful detached cottage is situated in the owner’s grounds in a peaceful location on the edge of Castleton village, nestling in the heart of the North York Moors National Park. Beautifully furnished. Woodburning stove. Pickering 19 miles. (Ref. 915326)

  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £290

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A stone building with a tiled roof next to a patio with yellow flowers and a hot tub at Thompson Rigg Barn in Langdale End near Thornton Dale
15
Langdale End near Thornton Dale, North York Moors National Park, YO13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This superb barn conversion is located on the outskirts of Langdale End, North Yorkshire. Woodburner. Studio style living. WiFi. Hot tub. Pickering 17 miles; Whitby 20 miles. (Ref. 997270)

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

7 nights from £631

Last booked 2 days ago
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A brick house exterior with two windows a small wooden fence and two wooden chairs in front garden at The Station Master's Office Loftus near Staithes
8
Loftus near Staithes, North Yorkshire, TS13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Annexe to former station master's house, in quiet Liverton village. Studio accommodation with separate kitchen. Rear patio garden with the novelty of a private goods train line at the end of the garden. Staithes 5 miles. (Ref. 922557)

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

7 nights from £276

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An outdoor patio with wooden table and bench seating next to a sliding door overlooking a river and houses at Old Joiners Shop Staithes
17
Staithes, North York Moors National Park, TS13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Cosy and comfortable converted cottage overlooking the beck in Staithes village. Bright, open plan living area, double bedroom, en-suite walk-in shower. All ground floor. Stone terrace with lovely views. WiFi. All amenities and beach 3 mins walk. (Ref. 927817)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher

7 nights from £403

Last booked yesterday
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A stone building with a red tiled roof gravel courtyard and wooden benches
26
Robin Hoods Bay, North York Moors National Park, YO22
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Well-appointed barn conversion located near the Yorkshire village of Robin Hood's Bay. Open-plan. Shared tennis court. WiFi. Beach and Cleveland Way close by. (Ref. 1002415)

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

7 nights from £351

Last booked 2 days ago
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A train station platform beside multiple railway tracks and a long stone building with windows at Repton @ Engine Shed in Whitby
17
Whitby, North Yorkshire, YO21
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A charming apartment named after a famous steam train and is situated in the town centre of Whitby. Open-plan living. Robin Hood's Bay 6 miles; Scarborough 19 miles. (Ref. 998766)

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

7 nights from £582

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An outdoor seating area with a barrel table holding a wine bottle and glasses overlooking a grassy field and a coastal cliffside at The Shepherds Rest in Robin Hoods Bay
37
Robin Hood’s Bay, North York Moors National Park, YO22
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A lovely studio-style shepherds hut resting in Robin Hoods Bay, North Yorkshire. In a National Park. Stunning bay views. Open-plan. Romantic. Close to amenities. Near a beach. Whitby 4.8 miles; Scarborough 18 miles. (Ref. 1109931)

  • Off-road parking
  • Ground floor bedroom

7 nights from £442

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A stone entryway with a gray door decorated with a wreath next to a potted tree at Brambles Apartment Sneatonthorpe near Ruswarp
19
Sneatonthorpe near Ruswarp, North York Moors National Park, YO22
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A stylish, first-floor apartment residing in Sneatonthorpe near Ruswarp, North York Moors. Pretty views. Smart TV. Couples retreat. Robin Hood's Bay 4.3 miles; Whitby 4.4 miles. (Ref. 1137764)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £421

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A red brick and white building with multiple windows and balconies with a palm tree and bushes in front at Sunset View in Whitby
37
Whitby, North Yorkshire, YO21
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, fourth-floor apartment with elevator, overlooking the Whitby Seafront and across towards Whitby Abbey. Pet free. Beach nearby. Sea views. Robin Hood's Bay 5.7 miles; Scarborough 19.7 miles. (Ref. 1123635)

  • Wi-fi

7 nights from £483

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Stone house with green shutters and red tiled roof surrounded by trees at New Stable Cottage in Lealholm
17
Lealholm, North York Moors National Park, YO21
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Stunning barn conversion set near Lealholm in the North York Moors National Park. Delightful garden. WiFi. Smart TV. Rural views. (Ref. 925536)

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

7 nights from £422

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A living room with arched windows black leather sofas a wooden coffee table a television and a floor lamp at Chapel-on-the-Hill in Grosmont
16
Grosmont, North York Moors National Park, YO22
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A fabulous Chapel conversion providing luxury two bedroom accommodation in this charming village with stunning long distance views. (Ref. 1015282)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £575

Last booked 8 hours ago
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A modern three-story brick building with glass balconies and a black garage door at The Office Gardens Apartment 1 in Whitby
Offer
20
Whitby, North Yorkshire, YO21
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Stylish first floor apartment within the town of Whitby in North Yorkshire. Balcony. Open-plan. En-suite. Smart TV. Off road parking. (Ref. 948080)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 10% off - Fri 25th Jul to 15th Aug 2025

7 nights from £710

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Row of terraced houses with different colored doors and a gravel garden path at Sunny Side in Runswick Bay
New property
35
Runswick Bay, North York Moors National Park, TS13
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

20 Hinderwell Lane is a lovely cottage resting in Runswick near Staithes in the North York Moors National Park, just a short walk to a pub and beach. Whitby 8.7 miles. (Ref. 1170630)

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

7 nights from £376

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Map View

Our holiday cottages in Glaisdale enjoy a central location within the North York Moors National Park. The village is placed excellently for a holiday of scenery, walking and exploring charming villages. Read on to discover what it is that make our Glaisdale cottages ideal for a UK break.

Lined with pretty stone buildings and surrounded by the picturesque Esk Valley, Glaisdale is a fabulous holiday base. It marks one of the last stops along the North York Moors Steam Railway. After passing through the breath-taking North York Moors, the train runs below the Grade II listed Beggar's Bridge within Glaisdale. Our holiday cottages in Glaisdale can make us of the assortment of friendly, traditional inns and local shops. The village's Ford Henry Butcher is known for its mouth-watering pork pies.

Walking and cycling paths are accessible within a stone's throw of our Glaisdale self-catering accommodation. Venture through rejuvenating, undulating countryside and discover the fascinating stories that the sleepy villages hold. You will recognise Goathland's railway station from its appearance in the Harry Potter films. Travel to the coast to find a wealth of fun-packed destinations; Whitby, Staithes and Saltburn should all be high on your agenda. The southern fringes of the North York Moors will present you with characterful market towns such as Kirkbymoorside and Pickering.

Use our years of experience and wealth of knowledge to embark on a memorable cottage holiday. Call 01244356666 today to speak to one of our helpful travel experts for more information.