Vacation rentals in Oswestry

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Top-rated vacation rentals in Oswestry

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

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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
4.86 out of 5 average rating, 311 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

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, 376 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 spacious entrance area is illuminated by natural light filtering through large windows. Exposed wooden beams create a warm ambiance, leading to a studio space featuring two large single beds positioned within a stone wall backdrop.
Guest suite in Llangollen
4.9 out of 5 average rating, 346 reviews

The Studio @ the Coachhouse

Light & modern ground floor studio accommodation with disabled access & private parking in gated property. 2 large single beds or zip & link huge Emperor double. Dog friendly Personal welcome from the owner or management team. 3 miles from Llangollen; 10 miles from Oswestry and Wrexham and 20 miles from Chester Plenty of local activities including the offas dyke path through the 150 private estate & the World Heritage Aqueduct a walk away. Dog friendly pub closeby. Plus super speed wifi.

Top guest favourite
A rustic barn structure, with a stone exterior and a small window, is set against a backdrop of lush green grass. The scene features scattered yellow flowers, and white clouds drift across a blue sky, enhancing the peaceful rural setting.
Farm stay in Church Stretton
4.93 out of 5 average rating, 229 reviews

Enchmarsh Farm barn

Small barn in the midst of a working Dairy and sheep farm right next to our home with fabulous walks all around. Double bed with small shower room and mini kitchen area in the corner of the room. Ideal as walking base or base when working in the area. Good parking just outside the barn - vehicles can be left whilst you walk the glorious hills around. Cooked breakfast available in the dining room in the farmhouse for £10 per person - includes the choice of sausage, bacon, eggs etc.

Superhost
A sitting area features a brick fireplace with a decorative mantel. Comfortable seating is provided by a yellow sofa with dark cushions and two matching chairs. A wooden coffee table sits in the center, and a vase of fresh flowers adds a welcoming touch. Natural light flows through the window.
Cottage in Shropshire
4.78 out of 5 average rating, 143 reviews

Charlotte's Web - rural town retreat near Wales

A cosy cottage in the idyllic market town of Ellesmere. A short walk from the mere itself and the park, together with all the town's amenities and the canal. Several pubs, restaurants and cafes are within a 10 minute walk. The location is ideal for exploring the north and West of Wales together with Cheshire and Shropshire. This property is conveniently situated close to the town's main bus stop providing links to Shrewsbury and Gobowen railway station. A lovely area to explore.

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, 179 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
The exterior of the annexe is illustrated, showcasing a two-story white building with a slate roof. The surrounding area features a gravelled driveway and green foliage, set against a backdrop of blue skies and scattered clouds.
Home in Llandrinio
4.94 out of 5 average rating, 116 reviews

SEVERNSIDE ANNEX

The annexe is situated next to our home with its own private access so you can be completely independent. It’s in the small village of Four Crosses near the England/Wales border and can sleep five people in two bedrooms, one king-size double and one family room comprising three single beds. The ground floor has an open plan living area with kitchen, dining area and sitting area. Outside there is off road parking for two cars and a gravelled patio with garden furniture.

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, 119 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.

Top guest favourite
The exterior of a wooden building is shown, featuring a staircase leading to a private entrance. The path is surrounded by gravel and lush green grass, with a gentle slope of hillside visible in the background.
Loft in Powys
4.91 out of 5 average rating, 432 reviews

Entire Loft with stunning views

Take it easy at this unique and tranquil getaway. The loft is a private accommodation suitable for up to 4 people. In a very quiet rural spot overlooking the Welsh countryside. Our accommodation is perfect for single travellers, couples or a small group of friends wishing to explore the area. Perfect location for walking Offas Dyke. The canal path runs 200 yards away. Snowdon is about 90 mins drive away.

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, 223 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.

Guest favourite
The garden house features a charming green exterior, complemented by a sloped roof and moss accents. Surrounding trees and shrubs enhance the sense of shade and seclusion. Windows framed by colorful flowers provide glimpses of the interior, inviting a tranquil atmosphere.
Tiny homes in Shrewsbury
4.93 out of 5 average rating, 718 reviews

The Garden House

Relax in our garden house in rural Shropshire. You'll be greeted by curious cats and chickens...and probably Allan and me. There's some fabulous walks, a lovely local and some pretty market towns all within easy reach. There's lots of interesting CDs to to play, is all we ask is that you return the CD to its case and to the appropriate place in the shelf.

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 vacation rentals

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Avg. price$156 CAD$164 CAD$178 CAD$169 CAD$176 CAD$174 CAD$178 CAD$180 CAD$184 CAD$181 CAD$177 CAD$173 CAD
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Quick stats about vacation rentals in Oswestry

  • Total vacation rentals

    Explore 40 vacation rentals in Oswestry

  • Nightly prices starting at

    Oswestry vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,150 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Oswestry vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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  5. Oswestry