Vacation rentals in Headington

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Top-rated vacation rentals in Headington

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

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Guest favorite
A modern kitchen and dining area are depicted, featuring a well-set dining table for eight. Stylish bar stools are arranged around a central island, complemented by sleek cabinetry and ample natural light from a skylight. Decorative touches include a vase of fresh flowers.
Home in Headington
4.98 out of 5 average rating, 99 reviews

New modern 4 bed, 3.5 bath house, free parking

A modern, spacious 4-bedroom, 3.5-bath house in a quiet residential area of Risinghurst. The home is bright, comfortable, and well equipped, with a fully fitted kitchen, fast Wi-Fi, large TV, washing machine, and free private parking. Ideal for families, professionals, and groups visiting Oxford, with easy access to the city centre, hospitals, and universities. This property is not suitable for babies or young children. There is no cot, high chair, or baby gates, more details in safety section.

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
4.97 out of 5 average rating, 233 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, 18 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
Guest suite in Headington
4.86 out of 5 average rating, 279 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
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 favorite
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 favorite
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.
Guesthouse in Headington
4.91 out of 5 average rating, 103 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, 539 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 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.
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 favorite
Apartment in Headington
5 out of 5 average rating, 20 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!

Guest favorite
Apartment in Headington
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.

Popular amenities for Headington vacation rentals

When is the best time to visit Headington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,523 GYDG$25,313 GYDG$26,569 GYDG$25,941 GYDG$26,569 GYDG$28,242 GYDG$30,543 GYDG$31,171 GYDG$29,079 GYDG$27,405 GYDG$25,941 GYDG$26,987 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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