British Travel Award Winners 2019!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards for an amazing 7th consecutive year.

Cleveland Cottages

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Your search returned 208 cottages

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  • Lobster Lodge

    Runswick Bay, North York Moors & Coast
    • Sleeps7
    • Bedrooms3
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    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)

    7 nights from £762

    Secure this property with a 30% deposit*
    Last booked 2 days ago
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  • Foulsyke Farm Cottage

    Loftus, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    A semi-detached, stone-built property resting on the outskirts of Loftus. Woodburning stove. WiFi. Pet-friendly. Off-road parking. Staithes 3.5 miles; Whitby 13.4 miles. (Ref. 1021276)

    7 nights from £329

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  • Rockpool Retreat

    Runswick Bay near Hinderwell, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A stunning, renovated lodge in a small, gated community, in Runswick, North Yorkshire. In the North York Moors National Park. Beach within walking distance. Contemporary interior. Whitby 8.9 miles; Middlesbrough 23.9 miles. (Ref. 1058617)

    7 nights from £501

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  • Walkers Halt

    Boulby near Staithes, North York Moors & Coast
    • Sleeps8
    • Bedrooms4
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    Semi-detached stone cottage on the Cleveland Way, near Staithes. Incredible sea views. Woodburning stoves. Large enclosed garden with summerhouse. Staithes 1.7 miles; Saltburn-by-the-Sea 8.1 miles; Whitby 11.7 miles. (Ref. 1018651)

    7 nights from £429

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  • Barn Cottage

    Hinderwell, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsYes
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    Delightful stone barn conversion in Hinderwell village. Spacious sitting room. Conservatory. WiFi. Excellent walking and cycling area. Runswick Bay 1 mile; Staithes 1.5 miles; Whitby 9 miles. (Ref. 1050446)

    7 nights from £418

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  • 7 Lilac Terrace

    Danby, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A mid-terrace, stone-built cottage resting in Ainthorpe near Castleton. WiFi. Woodburning stove. Whitby 16.6 miles. (Ref. 1044845)

    7 nights from £314

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  • Westonby Lodge

    Shortwaite near Lealholm, North York Moors & Coast
    • Sleeps8
    • Bedrooms3
    • PetsYes
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    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)

    7 nights from £549

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  • Mulgrave Cottage

    Port Mulgrave, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    Attractive, mid-terraced cottage in the quiet hamlet of Port Mulgrave on edge of Hinderwell village. Open-plan living. Open fire. Next to Cleveland Way. Staithes 1.5 miles, Whitby 9 miles. (Ref. 1022457)

    7 nights from £314

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  • Esklets Cottage

    Castleton, North York Moors & Coast
    • Sleeps6
    • Bedrooms4
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A charming mid-terrace stone cottage resting in the village of Castleton in the heart of the North York Moors. Enclosed courtyard. Master with en-suite. WiFi. Guisborough 9.2 miles; Whitby 15.5 miles; Pickering 20 miles. (Ref. 1046071)

    7 nights from £382

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  • Fair Holme

    Hinderwell, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    Delightful end-terrace character cottage in centre of Hinderwell. Cosy, open fire, en-suite bedrooms. Comfortable, well-equipped, accommodation. Beach 1 mile, Whitby 7 miles. (Ref. 1050474)

    7 nights from £379

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Just Show Me Cleveland Cottages


Wedged between the Heritage Coast and the northern fringes of the North York Moors National Park, our Cleveland holiday cottages are stepping stones to some fantastic attractions whether fun-filled adventure or peace and quiet rank high on your wish list.

Let's start at the coast and the broad, sandy beaches of Redcar - great for families and traditional seaside entertainment. Savour crab and lobster straight from the sea, slip into a wetsuit or have a flutter at the races. Enjoy exhilarating cliff-top walks along the Cleveland Way National Trail and take in the dizzying views from Boulby cliff. Saddle up at a local riding school and hack along the sands. Or ride the waves at Saltburn-by-the-Sea, a charming and historic resort that draws surfers from near and far - don't miss a pint or meal at The Ship Inn, once a favourite haunt of smugglers.

Cleveland's 'Captain Cook Country Tour'

Delve into the past tracing the steps of Cleveland's most famous explorer, Captain James Cook, taking in a variety of attractions including his birthplace along a 70-mile circular route.

Make the most of your Cleveland cottage's close proximity to the North York Moors National Park - a region of breathtaking natural beauty and ideal if you truly want to get-away-from-it-all. Enjoy leisurely drives along narrow, winding roads. Walk, cycle, fish, play golf - so much on offer, not to mention a welcoming range of sleepy villages, market towns and historic sites.

All in all, the best of coast and countryside when you book a Cleveland cottage holiday!