Vacation rentals in Headington

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Top-rated vacation rentals in Headington

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Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
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 *

Guest favorite
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
4.91 out of 5 average rating, 100 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 favorite
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, 529 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 favorite
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
4.98 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.

Top guest favorite
Apartment in Headington
5 out of 5 average rating, 20 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!

Top guest favorite
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, 81 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.

Superhost
A bright bedroom features a spacious bed with striped bedding, framed by a backdrop of natural wood paneling. A modern armchair and bedside table are positioned beside the bed. Large windows allow natural light to fill the room, enhancing the clean and contemporary design.
Apartment in Headington
4.71 out of 5 average rating, 55 reviews

** 1 Ashbrook Windmill - Luxury split level 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 1 is a is a brand new high specification first floor serviced apartment in the Headington area of Oxford. It comes with secure off street parking, unlimited high speed internet and weekly clean with towel and linen change. Pets incur additional cost.

Guest favorite
A mezzanine bedroom features a spacious bed adorned with green accent pillows. A decorative plant adds a natural touch. Soft light filters through the angled windows, illuminating warm wood tones and the surrounding textured walls. A wooden table displays neatly stacked towels, enhancing the room’s comfort.
Condo in St. Clement's
4.86 out of 5 average rating, 58 reviews

Kazbar Apartment – Luxe Oxford Stay

Kazbar Apartment is a stylish one-bedroom duplex tucked between vibrant Cowley Road and St Clements, just 10 minutes’ walk from Oxford’s historic centre. With an airy open-plan living space, designer kitchen, and romantic mezzanine bedroom, it’s perfect for couples or solo travellers. Surrounded by eclectic cafés, bars, and galleries, this chic hideaway blends boutique comfort with Oxford’s creative spirit.

Popular amenities for Headington vacation rentals

When is the best time to visit Headington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,520 GYDG$25,311 GYDG$26,566 GYDG$25,938 GYDG$26,566 GYDG$28,239 GYDG$30,540 GYDG$31,168 GYDG$29,076 GYDG$27,403 GYDG$25,938 GYDG$26,984 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Quick stats about vacation rentals in Headington

  • Total vacation rentals

    Explore 1,250 vacation rentals in Headington

  • Nightly prices starting at

    Headington vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 56,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    450 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    1,210 of Headington vacation 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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