Holiday houses in Headington

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Top-rated holiday rentals in Headington

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The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn in Great Milton
4.95 out of 5 average rating, 234 reviews

17th Century Barn in quiet country village

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

Top Guest favourite
The exterior of the brick cottage is visible, showcasing a traditional design with a sloped roof. Large windows allow natural light to enter, framed by lush greenery and garden boxes. The setting features a well-maintained lawn, enhancing the peaceful surroundings.
Cottage in Headington
4.94 out of 5 average rating, 141 reviews

The Coach house in Oxford

The Coach house, a lovely brick cottage built ~1880, has been renovated to provide an open plan, stylish interior. Upstairs sleeps 5 people with a downstairs bathroom. The historic city of Oxford (easily accessible by bus) provides plenty to do and the Thames and Cotswolds are lovely walking areas nearby. The cottage has it's own patio and garden area with trampoline. There is table football, games and books. Off road parking available. It is situated in the grounds of the owner's home.

Top Guest favourite
A cozy living area features a mix of seating, including a plush sofa and an armchair, arranged with two wooden coffee tables and a side table. Natural light filters through sliding glass doors leading to a balcony, while soft furnishings add a relaxed touch.
Apartment in Headington
4.92 out of 5 average rating, 66 reviews

Peaceful & Convenient Oxford Apt

A comfortable two-bedroom, two-bathroom apartment with generous living space and balcony. Quiet with a woodland view, yet ideally situated for local shops, Brookes University, Ruskin College, hospitals (adjacent to the John Radcliffe and The Manor, a short walk from the Churchill and NOC) and Headington School. There is an excellent bus service from nearby stops to Central Oxford (10 mins), London and Heathrow/Gatwick airports. Guests find 76 Beech Road a relaxing and convenient venue.

Guest favourite
A well-lit bedroom features a spacious bed adorned with a light blue patterned duvet and decorative pillows. Soft towels are neatly arranged on the bed. A stylish mirror and framed artwork complement the grey walls, with a welcoming entrance visible in the background.
Guest suite in Headington
4.86 out of 5 average rating, 281 reviews

The Annexe! A self contained Studio for 2 People

The ideal, cosy retreat in Headington! Re-decorated in Autumn 2024, the Annexe is a fully furnished and well equipped space, making a great and comfortable base for couples or solo travellers. With nearby great bars, restaurants, cafes, parks and shops, the property is also within walking distance of the John Radcliffe, Nuffield, Manor and Churchill hospitals as well as Oxford Brookes University. There are excellent transport links into Oxford city centre, London and major airports.

Guest favourite
Apartment in Northway
4.82 out of 5 average rating, 125 reviews

Oxford - Private Flat + Parking

Spacious Ground Floor 2 Bedroom Flat in Northway. Very close to central shops, restaurants, theatres, Oxtord University campus & Oxford Brookes University Campus, 10 minute drive to the centre of Oxford where you can explore the fascinating history of Oxford, Access to all high end clothing shops, Bodleian library, Museums etc. 5 minute walk to John Radcliffe hospital 15 minute walk to headington shops Bus stops to access the centre of oxford with buses running every 10-15 minutes.

Guest favourite
An open-plan living area showcases a combination of a light grey sofa, an inviting green armchair, and a central coffee table resting on a soft rug. A flat screen TV is mounted against a clean white wall, and a decorative fireplace adds character to the space.
Home in Headington
4.98 out of 5 average rating, 88 reviews

Spacious & Stylish Oxford Home

Stunning 2 bedroom Victorian home located in the heart of Headington, Oxford. Recently updated whilst retaining its period character features, this beautifully furnished property is the perfect place to stay while visiting Oxford. Just a 5 minute walk from Headington's London Road which is home to an abundance of restaurants and shops, and only a 10 min bus or taxi ride to Oxford's city centre. * Host My House manages this property which is owned by the Warner family *

Guest favourite
A living area features a dark blue sofa with a patterned throw pillow. A wooden coffee table sits in front, adorned with decorative items. A television and kitchen appliances are visible, while a sliding partition leads to a sleeping area with a light-colored bed and warm wall colors.
Guesthouse in Headington
4.88 out of 5 average rating, 107 reviews

Lovely 1-bed Annexe in LyeValley

Escape to the tranquility of Lye Valley in Headington. Our family-friendly accommodation, nestled on a peaceful residential street, provides a serene retreat. Surrounded by nature reserves and playgrounds, it's an ideal spot for families. ➣ Close to Churchill Hospital, Nuffield Hospital & Brookes University, it caters to medical & academic needs. ➣ A short bus ride from the Oxford city center offers easy access to landmarks like the Radcliffe Camera & Oxford Colleges.

Top Guest favourite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guesthouse in Garsington
4.95 out of 5 average rating, 542 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Guest favourite
A bright bedroom showcases a spacious bed with a textured duvet and cushions. A wall shelf holds books, while a black armchair complements the light wood furnishings. Natural light filters through two windows, providing a view of the greenery outside.
Apartment in Headington
4.97 out of 5 average rating, 61 reviews

Mini apartment with parking

Our apartment is ideally located within central Headington and perfect for a single person or couple. Accessed via a separate entrance to the main house, the apartment is completely self contained. The layout includes a bedoroom with standard double bed, large ensuite shower room, and separate kitchen. Guests have access to a shared garden, which includes a patio and BBQ area. The booking includes off street parking for a medium sized car.

Top Guest favourite
A spacious bedroom features a large bed adorned with decorative pillows and a textured throw. Flanking the bed, two windows provide natural light. A bench in front of the bed complements the elegant decor, which is highlighted by an art piece of foliage on the wall.
Apartment in Headington
5 out of 5 average rating, 22 reviews

Luxe Penthouse on Cuckoo Lane + JR Hospital

Can’t decide between a city break or a country getaway? Stay in this luxury penthouse overlooking Cuckoo Lane and have the best of both worlds - a modern residence close to the action yet decorated like a country pile with antiques and art. This fully furnished apartment has two large bedrooms with an open plan living and dining room which is filled with light from dawn to dusk. Perfect for exploring the City of Dreaming Spires!

Top Guest favourite
An open-plan studio layout showcases a cozy sitting area with a gray sofa, complemented by a vibrant rug. Natural light fills the space through large windows, illuminating the dining table and spacious bed. Art pieces adorn the walls, adding character to the room.
Apartment in Headington
4.99 out of 5 average rating, 88 reviews

West Lodge Studio

Newly renovated studio with private entrance adjoining a detached house. The apartment is set within a large, quiet garden in the attractive Old Headington conservation area. Exceptional views of the Oxfordshire countryside with access to our tennis court if requested. Easy access to Oxford by bus/car, JR hospital (5-minute walk), Headington shops and buses to London (10-minute walk). Off-street parking available.

Top Guest favourite
A spacious bedroom displays rustic wooden beams and a wooden king size bed adorned with dark blue cushions. A framed artwork featuring a heron is mounted on the wall, complementing the warm-toned decor. A mirror and bedside tables add functionality to the calming space.
Home in Marston
4.99 out of 5 average rating, 197 reviews

Fig at Church Farm Retreats - Unique Country Stay

​Fig is a one of a kind, stylishly furnished one bedroom self-catered holiday retreat consisting of a cosy open plan living room, separate modern kitchen, rustic wooden cladded partitioned bedroom with king size bed and ensuite shower room. With onsite parking for one car, landscaped garden with patio and bistro table overlooking the countryside and tennis court alongside the owners main farm house.

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Quick stats about holiday rentals in Headington

  • Total holiday rentals

    Explore 1,250 holiday rentals in Headington

  • Nightly prices starting at

    Headington holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 56,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    1,210 of Headington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Headington rentals

  • 4.7 Average rating

    Headington stays receive an average rating of 4.7 out of 5 from guests

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