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Holiday Cottages Oswestry

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Your search returned 104 cottages.

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  • Pear Tree Cottage

    Chirk, Shropshire
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A characterful semi-detached cottage resting in Chirk, Wrexham. Woodburning stove. Dog-friendly. Enclosed patio garden. Oswestry 5.5 miles; Llangollen 8 miles. (Ref. 1020449)

    1 customer review

    7 nights from £346

    Secure this property with a 30% deposit*
    Last booked 2 days ago
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  • Haimwood Byetake

    Llandrinio, Mid Wales & Cardigan Bay
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A stunning ground-floor annexe set in the scenic village of Llandrinio, Wales. Outstanding views. Accessible. Open-plan living. Welshpool 10.7 miles; Shrewsbury 15.4 miles. (Ref. 1001069)

    4 customer reviews

    7 nights from £418

    Secure this property with a 30% deposit*
    Last booked yesterday
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  • The Goat's Shed

    Knockin, Shropshire
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A detached barn conversion located in the village of Knockin in Shropshire. En-suite bathrooms. Open-plan. Enclosed courtyard. Pet-friendly. Oswestry 5.7 miles; Shrewsbury 13.5 miles. (Ref. 1059787)

    7 nights from £327

    Secure this property with a 30% deposit*
    Last booked yesterday
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  • Belmont Bridge

    Henlle, Shropshire
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    This charming semi-detached cottage rests next to the Shropshire Union Canal in the area of Henlle, Shropshire. Woodburning stove. Garden with seating. Off-road parking. Oswestry 5 miles; Llangollen 8.7 miles; Shrewsbury 22.2 miles. (Ref. 1057460)

    7 nights from £361

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  • Bryn Celyn

    Trefonen, Shropshire
    • Sleeps10
    • Bedrooms5
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    This detached holiday cottage rests in the peaceful village of Trefonen in Shropshire. Pet-friendly. Woodburning stove and open fire. Enclosed garden. Oswestry 2.9 miles; Shrewsbury 20.5 miles. (Ref. 1053089)

    1 customer review

    7 nights from £634

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    Last booked yesterday
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  • The Stables

    Knockin, Shropshire
    • Sleeps2
    • Bedrooms1
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A delightful semi-detached cottage resting in Knockin, Shropshire. Ground-floor living. Romantic retreat. Rural setting. Oswestry 5.7 miles; Shrewsbury 13.5 miles. (Ref. 1059788)

    1 customer review

    7 nights from £285

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    Last booked yesterday
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  • Lion's Den

    Ellesmere, Shropshire
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A charming, rustic townhouse resting at the centre of Ellesmere, Shropshire. Exposed beam ceilings. Stylish interiors. Close to amenities. Oswestry 11.8 miles; Whitchurch 12.8 miles; Shrewsbury 17.3 miles. (Ref. 954133)

    7 nights from £372

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  • Glanderwen

    Llanrhaeadr-Ym-Mochnant, Mid Wales & Cardigan Bay
    • Sleeps6
    • Bedrooms3
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A lovely three-bedroom bungalow resting in Llanrhaeadr-Ym-Mochnant, Wales. Woodburning stove. Ground-floor. Rural location. Lake Vyrnwy 12.9 miles; Welshpool 16.9 miles; Bala 19.5 miles. (Ref. 1046233)

    7 nights from £374

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  • Gwdihw

    Gobowen, Shropshire
    • Sleeps3
    • Bedrooms2
    • PetsNo
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A delightful rural cottage surrounded by countryside. Two bedrooms, open plan living area. Countryside walks and cycle rides from the door. Oswestry 4 miles (Ref. 951869)

    27 customer reviews

    7 nights from £299

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    Last booked yesterday
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  • Graig Gwyn Cottage

    Nantmawr near Trefonen, Shropshire
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A characterful, stone-built cottage situated on the outskirts of Trefonen. Rural location. Woodburning stove. WiFi. Welshpool 14.4 miles. (Ref. 1007316)

    12 customer reviews

    7 nights from £332

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    Last booked yesterday
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Just Show Me Oswestry Cottages

Straddling the Anglo-Welsh border, our Oswestry holiday cottages are firm favourites with lovers of history and countryside. Once an important frontier town, an ancient hill fort looms high above while Offa's Dyke National Trail marks the boundary. This unique setting allows you to pop in and out of England and Wales as many times as you like during your Oswestry cottage stay, giving you a real feel for the fusion of cultures.

On the Welsh side are historic treasures like the castles of Chirk, Powis and Whittington, said to be the former home of that famous pantomime character! Natural delights, meanwhile, include Lake Vyrnwy and Pistyll Rhaeadr waterfall, the highest in Wales.

Also close to your holiday home in Oswestry is the spectacular Pontcysyllte Aqueduct World Heritage Site, built by Thomas Telford - if you've a head for heights, experience mind-boggling scenery and travel across by horse-drawn barge.

Family days out include woodland walks and picnics in Nesscliffe Country Park, mini Land Rover rides and more at the award-winning Park Hall Farm and many other fantastic days out in and around Oswestry in Shropshire.

Exploring Oswestry

Back in town, join a themed walking tour and discover Oswestry's nooks and crannies. Much of the centre is a designated Conservation Area, with a wonderful mix of architectural styles. Dip in and out of the attractive shops, the tempting eateries and cosy pubs. And don't miss a trip to the market (three days a week) or monthly farmers' market.

Did you know Oswestry was voted one of the 'coolest places to live in England'? Find out for yourself and book that Oswestry cottage holiday soon!