Holiday houses in Oswestry

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Top-rated holiday rentals in Oswestry

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The stone barn conversion features a charming exterior with large, green-framed windows and a circular window accent. A small outdoor seating area with a white table and chairs is visible in front, complemented by lush greenery and ornamental grasses lining the pathway.
Guesthouse in Llangollen
4.89 out of 5 average rating, 213 reviews

The Cottage @ The Coachouse

A stone barn conversion with two double bedrooms and very large family bathroom Both bedrooms are either Superking beds or twins. Fully carpeted bedrooms and lovely wooden floors downstairs Large fully fitted kitchen plus dulce gusto coffee pod machine. Central heating in & constant hot water Large lounge/diner with double sofabed Gated property with outside seating & off street parking. Children & dogs welcome with child stair gates, window locks etc Cottage set in 150 acre private estate.

Top Guest favourite
A charming Victorian cottage features a red brick facade, complemented by decorative woodwork at the eaves. A window framed by greenery is visible, along with vibrant red foliage from a nearby plant, adding a touch of color to the exterior.
Cottage in Whittington
4.87 out of 5 average rating, 316 reviews

Village Cottage w/Garden & Free Parking/nr Castle

Cosy Victorian end-terrace cottage w/ small garden. Ideal for 2, sleeps 4. Village location by Whittington Castle ruin (see events & Kitchen at the Castle menu), plus 2 Family pubs. Explore local scenery, historic sites, hiking, cycling. Flexi Check-in after 3pm. All Enquiries welcome *7-day 10% discount * Handy for North Wales * Free double parking NB: Shower/toilet is downstairs. Stairs unsuitable for toddlers/infirm Old cottage may have cosmetic flaws while gradually making improvements

Guest favourite
The open-plan lounge and dining area feature high vaulted ceilings with rustic oak beams. A long wooden dining table is accompanied by colorful chairs, while a blue sofa set invites relaxation. Large windows allow natural light to illuminate the contemporary decor and artwork on the walls.
Home in Oswestry
4.95 out of 5 average rating, 118 reviews

Contemporary Converted Church, Oswestry

The Church is a charming converted Victorian church situated in a peaceful setting in the friendly town of Oswestry. The three-bedroom property retains many beautiful features with vaulted ceiling and rustic oak beams. The contemporary decor in the lounge offers a cosy place to enjoy the spectacular country views, with custom made arched windows and an open plan kitchen. We have under-floor heating, a stone bath and Egyptian Cotton Bedding. Find us using What3Words:///market.orbit.dumplings

Top Guest favourite
The entrance to Wisteria Cottage is framed by vibrant wisteria blooms cascading above the door. On either side, decorative potted plants stand in terracotta pots, complementing the charming white door adorned with a stained-glass window. Large windows alongside add natural light to the space.
Cottage in Oswestry
4.99 out of 5 average rating, 377 reviews

Wisteria Cottage Edgerley nr Shrewsbury/Oswestry

Wisteria Cottage is a self-contained private cottage in a quiet rural setting with countryside views, surrounded by nature. Newly refurbished with shabby-chic country inspired interior. Private WiFi, TV's both floors & super-king bed. Close to market towns of Shrewsbury & Oswestry, both 10 miles/15 minutes drive away. Private parking, central heating, 1-2 bedrooms, lounge, large fully equipped kitchen/dining area/family room. Main bedroom upstairs, two single beds in downstairs bedroom.

Top Guest favourite
A serene garden landscape is framed by a wooden fence, with vibrant flowers blooming along the path. A small wooden footbridge crosses over a gentle stream, surrounded by lush green foliage and tall trees. The scene captures a peaceful, natural setting.
Bungalow in Pen-y-Bont-Fawr
5 out of 5 average rating, 120 reviews

Tranquil Bungalow with Free Off Road Parking!

Take it easy at this unique and tranquil getaway! Beautiful bungalow set in the gateway to Snowdonia National Park. Private patio and garden area which includes a riverside seating area. A secure garden shed suitable for storage of bikes. 1 bedroom (with a king size bed) and a double sofa bed in the lounge area. Towels provided. A well equipped kitchen. Includes FREE wifi and parking. A post office/general store and 'The Railway Inn' (serves food) are both approximately 300 yards from stay.

Top Guest favourite
A small balcony features a round white table and two foldable chairs, overlooking a scenic view of rolling hills and the town below. A lantern sits on the table, adding a touch of charm. Bright skies and greenery are visible in the background.
Cabin in Sir Ddinbych
4.98 out of 5 average rating, 357 reviews

Unique dog friendly cabin in Llangollen.

Take it easy at this unique and tranquil getaway. Set in a cottage garden on a hillside above the town of Llangollen our lovely blue cabin has panoramic views across town towards Castell Dinas Bran and the Horseshoe Pass. Beautiful Llangollen is great for a break any time of year. Sit with a drink on the decking, or in front of the little log burner, and watch the sunset over the mountains, or the snow sweeping in along the valley. Take a glass of sparkly and have a bath under the stars.

Top Guest favourite
A traditional stone barn complex is set against a clear blue sky. The entrance features a neatly paved pathway leading to multiple holiday let units, each with a seating area. Flowering plants add color to the landscape, and a sign marks the property as Pentregaer Ucha Holiday Lets.
Cottage in Morda
4.99 out of 5 average rating, 180 reviews

The Barn at Pentregaer Ucha, tennis court & lake.

Charming one bedroom self catering holiday let in traditional stone barn. The Barn is one of four self catering units available at Pentregaer Ucha, alongside The Granary, The Nook and The Stables, all can be found listed separately on Airbnb making a perfect getaway for couples or groups. All our holiday lets offer everything you need for the perfect rural retreat and are decorated and maintained to the highest standards; an ideal base for exploring both Wales and Shropshire.

Top Guest favourite
An open plan studio apartment showcases a large glass door leading to a private balcony, with views of the surrounding greenery. Wooden bar stools are positioned near a counter, while a cozy seating area features a brown leather couch and a low wooden coffee table.
Loft in Llanymynech
4.96 out of 5 average rating, 237 reviews

Studio, kitchen + balcony. Detached + private.

Escape to the countryside and relax in this calming space with unspoilt country views. Newly built (2022), open plan private studio apartment near Arddleen, Llanymynech (Mid Wales). Perfectly located for Welshpool, Oswestry & Shrewsbury. Ideal for walking, cycling, family visits and short breaks. Situated above a detached garage at a private family home. Shared driveway with the main house. Parking for 2 cars. The Loft is the only airbnb at the property.

Guest favourite
A modern kitchen features dark cabinetry and sleek appliances, complemented by a spacious dining area with a round table set for four. A vibrant vase filled with flowers adds a touch of color to the scene, while windows provide natural light.
Apartment in Oswestry
4.96 out of 5 average rating, 121 reviews

Large luxury 1 bedroom suite in a beautiful garden

A uniquely located luxurious, spacious and peaceful apartment set within large garden grounds, yet only 5-10 minutes walk into Oswestry town centre. The apartment is well stocked with modern appliances and has lovely far reaching views over the Shropshire plain. Plenty of parking space is available and a separate laundry room is available to use on-site at no extra cost. Key code available for late check-ins.

Guest favourite
A cozy lounge area features a green leather sofa and a plush rug. Natural light streams in through a large window, illuminating two wooden dining chairs positioned beside a small table. The kitchenette is visible in the background, enhancing the comfortable living space.
Condo in Shropshire
4.8 out of 5 average rating, 286 reviews

Beautiful base to explore stunning surroundings.

A fantastic apartment set in the beautiful Shropshire countryside just off the A5 between Shrewsbury-Oswestry with excellent parking facilities to explore a wealth of local walks, amazing Archaeology & stunning places to visit. A stunning base in the perfect location, for couples, work placements, Ramblers, Business travellers, stop overs and adventure motorcyclists etc. Check in 4pm - Check out 10am

Guest favourite
A rustic exterior view of a charming structure features a prominent arched wooden door emphasizing the historic character. The white brick wall complements the slate roof, while a small potted plant is positioned near the base of the door. Natural light softly illuminates the space.
Apartment in Oswestry
4.82 out of 5 average rating, 224 reviews

Old Chapel

Due to the current situation l am happy to consider longer stays for workers and will offer discounts so please enquire. A unique lovingly renovated hideaway, very convenient for anyone visiting the town of Oswestry. Three minutes walk to the park, the ancient Church and Heritage Centre. The town has many restaurants, pubs and cafes, galleries and other attractions.

Superhost
The exterior of a large period property is showcased, featuring a stone facade and a charming conservatory. Lush greenery surrounds the building, complemented by vibrant flower baskets. The roof is adorned with multiple chimneys, while a gravel path leads to the entrance.
Guest suite in Whittington
4.81 out of 5 average rating, 340 reviews

Self Contained West Wing with own sauna

Beautifully renovated spacious wing of large period property. Available for minimum 7night booking arriving on a friday One double bedroom (standard double bed) with , en-suite,hairdryer sauna, shower & WC, large living/dining room with solid fuel burner, kitchen with hob, microwave, small electric oven and under counter fridge. Dog friendly

Popular amenities for Oswestry holiday rentals

When is the best time to visit Oswestry?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$199 NZD$209 NZD$227 NZD$214 NZD$223 NZD$222 NZD$239 NZD$236 NZD$227 NZD$230 NZD$225 NZD$220 NZD
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Quick stats about holiday rentals in Oswestry

  • Total holiday rentals

    Explore 40 holiday rentals in Oswestry

  • Nightly prices starting at

    Oswestry holiday rentals start at $71 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,150 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Oswestry holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oswestry rentals

  • 4.9 Average rating

    Oswestry stays are highly rated by guests—averaging 4.9 out of 5!

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  3. England
  4. Shropshire
  5. Oswestry