Cleveland Cottages

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Your search returned 153 cottages.

All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

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    • Sleeps8
    • Bedrooms4
    • PetsNo

    Beautifully renovated stone barn conversion, in small group of three near Staithes fishing village. Open plan living area, 4 bedrooms, stone floors, character beams. WiFi, rear elevated garden. Excellent walking area. Staithes 2 miles. (Ref. 927339)

    Last booked yesterday

    7 nights from £396

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    A fresh, mid-terrace cottage in the centre of Guisborough in North Yorkshire. By North York Moors. Amenities walking distance. Coast 6 miles. (Ref. 969655)

    Last booked yesterday

    7 nights from £357

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    • Customer Rating: 4 out of 4

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Charming detached stone cottage in popular village of Hinderwell, just north of Whitby. Well-presented open plan living area, off road parking nearby, small sunny courtyard. Local pub and shops 2 mins walk, beach 10 mins walk. (Ref. 942487)

    Last booked within the last 2 days

    7 nights from £266

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Ground floor cottage in peaceful setting near Castleton village. Cosy sitting room with bay window, lovely walks in the area. Pleasant views. Guisborough 8.5 miles. (Ref. 914908)

    Last booked within the last 2 days

    7 nights from £284

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    A characterful, three-storey cottage in Newholm, close to Whitby in North Yorkshire. Countryside views. Exposed beams. (Ref. 984423)

    7 nights from £280

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Charming, terraced fishing cottage in Staithes. Character cottage with panelling, beams and woodburning stove. Spacious sitting room, sunny rear courtyard. Beach, pubs and shops 2 mins walk. Whitby 10 miles. (Ref. 933838)

    Last booked yesterday
    • 5% off - Fri 11th Jan to 1st Feb 2019

    7 nights from £308

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    • Sleeps5
    • Bedrooms2
    • PetsYes

    A cosy stone-walled cottage based in the calming hamlet of West Barnby. Views all around. Open fire. Decking area. Perfect holiday location. Whitby 6 miles. (Ref. 960331)

    Last booked 6 hours ago

    7 nights from £302

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    • Customer Rating: 3.8 out of 4

    • Sleeps4
    • Bedrooms2
    • PetsYes

    Cosy, characterful old fisherman's cottage in quiet corner of Staithes village. Open plan living area, woodburner, 3 mins walk to beach, pub, shops. Wonderful walking and touring area with North York Moors on the doorstep. Whitby 10 miles. (Ref. 926017)

    Last booked within the last 2 days

    7 nights from £310

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    • Sleeps3
    • Bedrooms1
    • PetsYes

    Perfect retreat for up to three guests in the pretty market town of Guisborough. Multi-fuel stove, secure storage for bikes and full of original features, this is a super holiday choice. (Ref. 936036)

    Last booked within the last 2 days

    7 nights from £295

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Traditional end-terrace cottage in quiet location above Saltburn Beach. Open fire in original fireplace, off road parking, lovely views. Ten mins walk to beach and town centre. Excellent walking area and easy access to coastal towns. (Ref. 929674)

    Last booked 6 hours ago

    7 nights from £245

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All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

*Applicable to holidays commencing at least 6 weeks in the future. Full balance due 6 weeks prior to departure. Please refer to Book Now Pay Later Terms and Conditions for further information.

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!