Holiday rentals in Headington

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Top-rated holiday rentals in Headington

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

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Superhost
Home in Headington
5 out of 5 average rating, 3 reviews

Modern 3BR | Parking | Oxford Brookes | Hospital

🏳 Spencer & Jackson Short Lets & Serviced Accommodation Oxford 🏳 Spencer & Jackson welcome you to our stunning 3-bed house in the heart of Headington, Oxford with 2 free allocated parking spaces! Set across 2 spacious floors, this newly renovated home is ideal for groups and families. Just a short journey into Oxford City Centre. 🏡 3 - Bedroom House 🗝 Sleeps Up to 5 Guests 🗝 Bedroom 1 - 1 x Double Bed 🗝 Bedroom 2 - 1 x Double Bed 🗝 Bedroom 3 - 1 x Single Bed 🗝 Bathrooms x 2 🗝 Garden

Top guest favourite
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
4.96 out of 5 average rating, 228 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, 140 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
Home in Headington
4.94 out of 5 average rating, 17 reviews

Central Headington great location

A characterful and spacious period home with parking space and private rear garden, set in a quiet residential side street in the heart of Headington. Buses to Central Oxford, London and airports are only a few steps away, along with numerous shops and Headington's vibrant array of restaurants, cafes and takeaways. Bury Knowle Park's 7 hectares of green space is just across the road, where you can find all sorts of attractions and activities to engage in, or just unwind with a peaceful walk.

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, 276 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
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, 85 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 *

Top guest favourite
A cozy bedroom features a spacious bed dressed in neutral tones and accented with a decorative striped pillow. A blue throw blanket is spread across the bed. A tea set, complete with a teapot and a cup, is arranged on a tray next to a small vase with flowers.
Home in Headington
4.97 out of 5 average rating, 29 reviews

House in Oxford

Experience Oxford at its finest from this beautifully refurbished holiday home, located in one of the city’s most sought-after neighbourhoods. Perfect for families, couples, academics, or professionals, this elegant property offers the ideal blend of comfort, style, and convenience. Off-street parking is available, and excellent public transport links make it easy to explore Oxford’s colleges, museums, and cafes, or even take a day trip to the Cotswolds or London.

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.
Guest house in Garsington
4.95 out of 5 average rating, 524 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.

Top 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.
Flat in Headington
4.98 out of 5 average rating, 53 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.

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.
Flat in Headington
5 out of 5 average rating, 18 reviews

Luxe Penthouse on Cuckoo Lane

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!

Guest favourite
Flat in Headington Quarry
5 out of 5 average rating, 7 reviews

Bell House Oxford - The Cloakroom

Bell House Oxford - The Cloakroom is a compact ground floor studio in vibrant Headington, ideal for solo travellers or couples. It features a double bed, dining area, small kitchen area and modern en suite with rain shower. Bright and thoughtfully designed, it offers on-site parking, a shared garden, and high-speed Wi-Fi. Perfect for business or academic stays, with easy access to hospitals, research centres and Oxford University.

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.
Flat in Headington
4.99 out of 5 average rating, 80 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.

Popular amenities for Headington holiday rentals

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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 $13 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wifi availability

    1,210 of Headington holiday rentals include wifi 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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  3. England
  4. Oxfordshire
  5. Headington