Holiday houses in Headington

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Top-rated holiday rentals in Headington

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Guest favourite
The outdoor patio features a smooth stone pathway leading to a glass door entrance. Lush greenery surrounds the area, creating an inviting space. Warm lighting fixtures can be seen on the exterior walls, enhancing the tranquil ambiance of the courtyard.
Home in Headington
4.91 out of 5 average rating, 56 reviews

3-Bed home with Garden & Parking

Experience Oxford in this beautifully maintained 3-bedroom house, ideally in a peaceful community across from a park. The house features a lovely garden, perfect for enjoying morning coffee or evening relaxation. Inside, you'll find a bright, open kitchen and dining area, ideal for family gatherings after a day of exploring. The private parking space and close proximity to Oxford Brookes University and Churchill Hospital make this home a perfect choice for both short and long stays in Oxford.

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
Home in Headington
4.98 out of 5 average rating, 89 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, 31 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
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.

Guest favourite
A studio flat features a double bed covered with white linens and a green throw. A small desk is positioned next to a television mounted on the wall. An armchair is visible, while a window allows natural light to brighten the space.
Apartment in Headington
4.78 out of 5 average rating, 165 reviews

Yew Studio - Self contained one bed with parking

Self-contained one bed studio flat with its own entrance next to our house The studio flat is a new extension to our house with its own entrance. There is a double bed and a wardrobe. A small fridge/freezer and a combinational microwave cooker are also in the flat. You can cook light meals if you like. The local restaurants, shops and pubs are within a few minutes walking distance. Free WiFi. One parking space in front of the house can be provided upon request.

Top Guest favourite
A cozy open-plan studio showcases a comfortable sofa set opposite a round wooden table adorned with a black vase and decorative white flowers. The sleeping area features a spacious bed tucked against the wall, complemented by light wood shelves displaying plants and decor.
Guesthouse in Headington
4.96 out of 5 average rating, 90 reviews

Detached Cottage Near JR Hospital + Parking

Welcome to our cottage, a peaceful retreat in the HEART OF HEADINGTON. This open-plan studio comfortably accommodates up to 3 guests. Enjoy FREE PARKING, a rare perk in central Headington. Just 5 min walk to JOHN RADCLIFFE HOSPITAL and a 10m ride to OXFORD CITY CENTRE. Our cottage offers comfort, convenience, and charm, nestled on a quiet side road for a serene stay. SHOPS, RESTAURANTS and BROOKS UNIVERSITY are also within walking distance. Ultrafast Wi-Fi.

Superhost
Apartment 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.

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, 63 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.

Superhost
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 Oxfordshire
4.84 out of 5 average rating, 68 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 holiday rentals

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Avg. price$209 NZD$208 NZD$218 NZD$213 NZD$218 NZD$232 NZD$250 NZD$256 NZD$238 NZD$225 NZD$213 NZD$221 NZD
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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 $17 NZD 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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