Holiday rentals in Headington

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Top-rated holiday rentals in Headington

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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.

Guest favourite
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
Flat 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
A dining area is presented with a round wooden table set for four, surrounded by light wooden chairs. A soft rug covers the floor, and a fireplace adds character. A mirror above the mantel reflects soft lighting, enhancing the room's inviting feel.
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 modern kitchen and living area features sleek cabinetry and a well-equipped countertop. A comfortable sofa is positioned beside a dining table, while light streams through partially covered windows. A door leads to the outside, enhancing the open feel of the space.
Guest house 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
Home in Headington
4.95 out of 5 average rating, 20 reviews

Central Headington great location

This characterful and spacious period home has a private parking space and a lovely enclosed 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, offering a range of activities and a great place to unwind.

Superhost
Flat in Headington
4.84 out of 5 average rating, 25 reviews

** 2 Ashbrook Windmill - Luxury ground floor 1 bedroom flat ****

Ashbrook Serviced Apartments provide over 20 serviced apartments of all sizes across Oxfordshire. See our web page for further information.Ashbrook Windmill Flat 2 is a brand new, high specification ground floor serviced apartment in the Headington area of Oxford, UK. The apartment, thoughtfully renovated in 2019, comes with secure off street parking, unlimited high speed internet and weekly clean with towel and linen change. Pets incur additional cost.

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, 543 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 well-equipped kitchen area features modern appliances, including two ovens and a stovetop. A wooden countertop is complemented by a breakfast bar with two stools, set beside a window that provides a view of the garden outside.
Flat in Headington
4.97 out of 5 average rating, 62 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.
Flat 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
Flat 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
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.

Popular amenities for Headington holiday rentals

When is the best time to visit Headington?

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Avg. price$157 SGD$155 SGD$163 SGD$159 SGD$163 SGD$173 SGD$188 SGD$191 SGD$179 SGD$168 SGD$159 SGD$166 SGD
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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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