Holiday Cottages Oswestry

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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.

Holiday Cottages Oswestry

REFINE SEARCH

Your Oswestry/Croeswallt, Shropshire search returned 137 cottages

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Map View
Stone buildings with slate roofs and solar panels surrounded by garden and trees at Little Cow House in Pontfaen near Chirk
35
Pontfaen near Chirk, Shropshire, LL14
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A superb, three bedroom barn conversion set in the Ceiriog Valley overlooking the Chirk Aqueduct and Viaduct close to Chirk. Welcoming character property with modernised fixtures and features. Chirk 1 mile. (Ref. 929056)

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


for 7 nights £442

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Little Barn - 1172562 - photo 1
33
Trefonen, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Little Barn is a gorgeous, stone period cottage situated in the rural village of Trefonen, Shropshire, enjoying a toasty woodburning stove and a Smart TV. Oswestry 2.9 miles; Llanhaeadr-ym-Mochnant 10.6 miles; Shrewsbury 20.2 miles. (Ref. 1172562)

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


for 7 nights £374

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A stone and wood house with a fenced lawn and a wooden gate at The Old Cart House in Nantmawr near Trefonen
33
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A traditional and rustic property boasting contemporary charm, this detached dwelling is perfect for your family getaway to Shropshire. Ideal for exploring both England and Wales. Open-plan living. Countryside views. On a working farm. Trefonen 2.7 miles. (Ref. 986887)

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


for 7 nights £407

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White exterior of a house with grey window frames and door with plants outside at Little Beeches in Hengoed
22
Hengoed, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Tremendous, semi-detached cottage well-placed in the village of Hengoed, Shropshire. Exposed stonework. WiFi. Llangollen 10 miles. (Ref. 958275)

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


for 7 nights £372

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A white stone house with a slate roof surrounded by bushes and a tree along a driveway at Penymaes in Bronygarth near Chirk
31
Bronygarth near Chirk, Shropshire, SY10
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Superb detached cottage in beautiful country location. Woodburning stove, WiFi. Llangollen 9 miles. (Ref. 916332)

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

  • 5% off - Mon 27th Oct to 3rd Nov 2025

  • 5% off - Fri 31st Oct to 7th Nov 2025

  • 37% off - Tue 30th Dec 2025 to 6th Jan 2026


for 7 nights £493

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A two story house with white walls a gray roof and a garden with trees and bushes at Belmont Bridge in Henlle
35
Henlle, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

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)

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


for 7 nights £741

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A brick house with a gravel driveway and garden at 1 Clarkes Lane in St Martins
47
St Martins, Shropshire, SY11
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

1 Clarkes Lane is a beautiful cottage nestled in the quaint village of St Martins in Shropshire. Woodburning stove. Hot tub. Pet-friendly. Games room. Oswestry 5.3 miles; Llangollen 9.8 miles; Shrewsbury 22.4 miles; Chester 23.5 miles. (Ref. 1159443)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £862

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An outdoor patio area with seating and a fire pit by a stone house with ivy and a pond with water lilies in the foreground at Tanat House Nantmawr near Trefonen
86
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps14
  • Bedrooms7
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Tanat House is a wonderful, pet-friendly detached holiday home situated in the outskirts of of Nantmawr in Shropshire with an indulgent private hot tub. Oswestry 4.1 miles; Llanhaeadr-ym-Mochnant 9.2 miles; Shrewsbury 19.7 miles. (Ref. 1155356)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £2321

Last booked 2 days ago
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A brick house with a slate roof and wooden fence surrounded by plants and trees at The Tractor Shed in Kinnerley near Oswestry
25
Kinnerley near Oswestry, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Well-appointed barn conversion nestled close to the Wales/England border, some 8 miles from the centre of Oswestry. WiFi. Pet-friendly. Off-road parking. Enclosed garden. Llanymynech 4.1 miles. (Ref. 1000425)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights £419

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A brick house with driveway potted plants and trees at Plum Hill Studio in Oswestry
19
Oswestry, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A cosy, ground floor studio apartment located just outside of Oswestry in Shropshire. Open plan. Delightful lawn. Oswestry 1 mile. (Ref. 963200)

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


for 7 nights £282

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An outdoor stone patio area next to a stone building with several windows and doors at Sally's Barn in Weston Rhyn
29
Weston Rhyn, Shropshire, SY10
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Sally's Barn is a delightful, pet-friendly holiday home resting in the little village of Weston Rhyn in Shropshire with a toasty woodburning stove. Oswestry 4.9 miles; Wrexham 10.7 miles; Whitchurch 19.5 miles. (Ref. 1168115)

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


for 7 nights £738

Last booked 1 hour ago
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A stone and timber house with a gravel driveway and garden at Pentre Hall in Bronygarth near Chirk
70
Bronygarth near Chirk, Shropshire, SY10
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Pentre Hall is a characterful, five-bedroom property in Bronygarth near Chirk, Shropshire. Clwydian Range and Dee Valley AONB. Original features. Hot tub. Oswestry 5.7 miles; Llangollen 8.8 miles; Chester 24.4 miles. (Ref. 1112629)

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


for 7 nights £1578

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A white two-story house with a stone patio and garden chairs near a gravel driveway at Bryn Celyn in Trefonen
34
Trefonen, Shropshire, SY10
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

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)

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


for 7 nights £856

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Pen Y Bont - 939502 - photo 1
22
Glyn Ceiriog, Wrexham, LL20
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A beautiful, detached, Welsh cottage, set in the Ceiriog Valley, two miles from Glyn Ceiriog. Peaceful countryside views. Character features and contemporary design. Woodburning stove. WiFi. Llangollen 7 miles. (Ref. 939502)

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


for 7 nights £673

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A gravel driveway leading to a brick house with lamp posts and a wooden gate at Rhandregynwen Hall in Four Crosses
81
Four Crosses, Powys, SY22
  • Sleeps18
  • Bedrooms8
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A captivating cottage set on spectacular grounds just outside of Four Crosses, Wales. Contemporary and exquisite. WiFi. Two sitting rooms. Hot tub area. Four Crosses 1.7 miles, Shrewsbury 16.6 miles. (Ref. 929065)

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


for 7 nights £2463

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A white cottage with a gravel driveway wooden seating area and hedges at Pennal Cottage in Maesbury Marsh near Knockin
41
Maesbury Marsh near Knockin, Shropshire, SY10
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Pennall Cottage is a lovely property near Knockin, Shropshire, boasting countryside views to admire, a woodburning stove and a hot tub in the front garden. Oswestry 3.5 miles; Shrewsbury 15.5 miles. (Ref. 935032)

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


for 7 nights £641

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A driveway in front of two brick and timber framed buildings with outdoor chairs and potted plants at The Wynnstead Annexe Queen's Head near Oswestry
20
Queen's Head near Oswestry, Shropshire, SY11
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

This first floor apartment is set above a garage in the owner's grounds and is an ideal romantic retreat. Private patio, short walk to pub and canal. Oswestry 4 miles. (Ref. 954032)

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


for 7 nights £333

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A cabin with a deck and steps in a grassy area at Cheviot in Oswestry
18
Moelfre near Oswestry, Powys, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Cheviot is a charming, pet-friendly shepherd's hut resting in the village of Moelfre, Powys, boasting an enclosed garden, hot tub, and lovely rural views. Welshpool 17.9 miles; Llangollen 18.3 miles; Wrexham 19.7 miles; Shrewsbury 25.3 miles. (Ref. 1177569)

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


for 7 nights £456

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An exterior view of a white house with black timber framing a hedge and signs reading Top Farm Lodge and Top Farm Cottage at Top Farm House in Knockin
64
Knockin, Shropshire, SY10
  • Sleeps13
  • Bedrooms7
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

An incredible and unique Grade II listed, 17th century farmhouse resting in the village of Knockin, Shropshire. Original features. Woodburning stoves. Private gardens. Oswestry 5.7 miles; Shrewsbury 13.5 miles. (Ref. 1052679)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room


for 7 nights £1615

Last booked 1 hour ago
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A garden patio with two reclining chairs yellow flowers a small table with two chairs a bench and a wooden gate at Cam O'r Fechan Annexe in Llangollen
29
Llangollen, Denbighshire, LL20
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A single-storey annexe lying on the luscious outskirts of Llangollgen in North Wales. Single-storey. Open-plan living. Countryside views. Romantic. Private terrace with furniture. Ruthin 17.2 miles; Mold 23.1 miles; Chester 24.9 miles. (Ref. 1110492)

  • Wi-fi
  • Off-road parking


for 7 nights £356

Last booked yesterday
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Map View

 

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!