These holiday cottages in Castleton, North Yorkshire are set in the breathtaking countryside of the North Yorkshire Moors. Castleton is the main village in the Upper Esk Valley and home to many great walking routes, bird-watching spots and local pubs.

If you're looking for a rural holiday to remember then these holiday cottages in and around Castleton, North Yorkshire are for you. Looking to explore the area further? Why not explore the picturesque market towns of Grosmont and Egton or head to Whitby and enjoy a day at the seaside. 

found 21 cottages
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Rockpool Retreat

Runswick Bay near Hinderwell, North York Moors & Coast
A beautifully-presented lodge in a small, gated community in Runswick, North Yorkshire. In North York Moors National Park. Pet-friendly. Electric fire. Barbecue. Staithes 2.4 miles; Whitby 9.1 miles; Saltburn-by-the-Sea 11.1 miles.(Ref. 1112653)
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Per week £576
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Ammonite Lodge

Runswick Bay near Staithes, North York Moors & Coast
An attractive, detached lodge in a small, gated community in the stunning Runswick Bay. Open-plan living. Off-road parking. Garden. Children welcome. Staithes 2.4 miles; Whitby 8.9 miles. (Ref. 1112943)
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Per week £625

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Pebble Cottage

Hinderwell, North York Moors & Coast
An attractive mid-terrace traditional cottage sitting in Hinderwell, North Yorkshire. Open-plan. Woodburning stove. Close to beach. Dog-friendly. Whitby 8.9 miles.(Ref. 1104367)
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Per week £379

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Michaelmass Cottage

Castleton, North York Moors & Coast
A delightful two-bedroom, stone-built cottage resting in Castleton in North Yorkshire. Smart TV. Woodburning stove. Close to amenities. Guisborough 9.6 miles; Whitby 17.5 miles; Pickering 21.7 miles.(Ref. 1085226)
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Per week £387

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Hideaway Lodge

Runswick Bay, North York Moors & Coast
A charming lodge with beautiful décor in the fabulous village of Runswick Bay, North Yorkshire. Open-plan living. Beach nearby. Off-road parking. Staithes 2.6 miles; Whitby 9 miles. (Ref. 1097511)
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Per week £555

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Limber View

Grosmont, North York Moors & Coast
4 Stars Gold
A fabulous former village school converted to provide luxury two bedroom accommodation in this charming village surrounded by open countryside.(Ref. 1015656)
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Per week £531

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Huckleberry

Runswick Bay near Staithes, North York Moors & Coast
A stylish and contemporary ground-floor lodge resting on The Pines in Runswick Bay, North Yorkshire. Chic interior. Close to the coast. Within National Park. Whitby 8.9 miles; Danby 9.4 miles; Robin Hood's Bay 13.9 miles. (Ref. 1054717)
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Per week £522

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Preacher's Rest

Grosmont, North York Moors & Coast
5 Stars Gold
A fabulous Chapel conversion providing luxury three bedroom accommodation in this charming village surrounded by open countryside.(Ref. 1015645)
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Per week £541

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Roxby Cottage

Staithes, North York Moors & Coast
With views of the sea, harbour and beach, this pretty cottage on the seafront in the picturesque village of Staithes is beautifully furnished and ideal for a wonderful seaside holiday(Ref. 1015761)
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Per week £690

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Bracken Howe Lodge

Egton, North York Moors & Coast
Wow! Luxurious lodge with a wonderful hot tub, set in beautiful woodland with stylish accommodation and a veranda for dining outside - bliss!(Ref. 1015816)
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Per week £849

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The Old Dairy, Ellerby

Runswick Bay, North York Moors & Coast
A superb four-bedroom Grade II listed barn conversion resting in Ellerby near Staithes, North Yorkshire. Rural sea views. In the North York moors National Park. Smart TV. Enclosed garden. Whitby 7.7 miles.(Ref. 1090629)
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Per week £716

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Wheatsheaf Cottage

Whitby, North York Moors & Coast
An idyllic stone-built cottage in this glorious village, lovingly restored and thoughtfully designed, providing comfortable accommodation for all ages - a charming cottage in a perfect location.(Ref. 1015660)
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Per week £806
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Pond Farm View

Hinderwell, North York Moors & Coast
A charming three-bedroom property situated in Hinderwell, North Yorkshire. Conservatory. Off-road parking. Enclosed garden. Pet-free. Runswick Bay Beach 1 mile; Staithes Fishing Village 1.5 miles; Sandsend Beach 6.5 miles; Whitby 8.9 miles. (Ref. 1094665)
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Per week £445

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Manor Cottage

Whitby, North York Moors & Coast
Manor Cottage is a lovely period house located on the stunning Egton Estate – with its 6000 acres of magnificent woodland, pastures and moorland plus the beautiful manor house – and combines elegance with a cosy atmosphere, perfect for a family holiday.(Ref. 1015678)
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Per week £597

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Lobster Lodge

Runswick Bay, North York Moors & Coast
A stunning and luxurious lodge in the idyllic fishing village of Runswick Bay. Close to the beach. Stylish interior. Enclosed decking. Whitby 8.7 miles; Saltburn-by-the-Sea 11.2 miles; Goathland 14.7 miles. (Ref. 1058853)
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Per week £726

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Bramblewick

Runswick Bay near Staithes, North York Moors & Coast
A contemporary single-storey lodge resting on The Pines holiday home development in Runswick Bay, North Yorkshire. Open-plan. Decking. Close to the beach. Staithes 2.8 miles; Whitby 9 miles; Saltburn-by-the-Sea 11.5 miles.(Ref. 1076816)
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Per week £522

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Chapel-on-the-Hill

Grosmont, North York Moors & Coast
5 Stars Gold
A fabulous Chapel conversion providing luxury two bedroom accommodation in this charming village with stunning long distance views.(Ref. 1015282)
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Per week £531

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Seagull Lodge

Runswick Bay, North York Moors & Coast
A single-storey lodge on The Pines at Runswick Bay holiday park in Runswick Bay on the North Yorkshire coast. Close to beach. Decking area. Open-plan living. Staithes 2.4 miles; Whitby 8.9 miles; Saltburn-by-the-Sea 11.1 miles.(Ref. 1074088)
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Per week £548

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Esk View Cottage

Grosmont, North York Moors & Coast
A charming river-front cottage which has been newly refurbished and decorated, in a picturesque spot in the lovely village of Grosmont. (Ref. 1015777)
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Per week £500

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Sunday Cottage

Grosmont, North York Moors & Coast
Wheelchair Accessible 4 Stars Gold
A fabulous former village school converted to provide luxury three bedroom accommodation in this charming village with stunning long-distance views and offering a suite for those with mobility issues.(Ref. 1015657)
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Per week £531

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The Barn, Ellerby

Runswick Bay, North York Moors & Coast
5 Stars Gold
A stunning luxury barn conversion with fabulous hot tub, private gardens and paddock, located in a beautiful village near the picturesque Runswick Bay.(Ref. 1015690)
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Per week £1620