Holiday rentals in Headington

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Top-rated holiday rentals in Headington

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Guest favourite
The open plan kitchen and dining area features a bright design with a large window and skylight allowing natural light. A white dining table with matching chairs is set for a meal. Modern cabinetry complements the spacious layout, with a few appliances visible in the background.
Home
4.85 out of 5 average rating, 120 reviews

Spacious 3bed2bath Family Home + parking Garden

Welcome to my spacious 3 bedroom two storey semi-detached family house. The house has a large open plan kitchen and living area on the ground floor. Two bedrooms, an office and a bathroom on the first floor. One ensuite bedroom on the ground floor. The house provides easy access to the heart of Oxford, John Radcliffe Hospital and Oxford Brooks University. It has been decorated to host quiet, considerate and respectful guests. Long term stays are available. Party or event are strictly forbidden.

Superhost
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
4.95 out of 5 average rating, 234 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
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
5 out of 5 average rating, 103 reviews

Countryside Retreat with hot tub

This modern country retreat features panoramic views of the Oxfordshire countryside from the open-plan kitchen, living room. Ideal for a peaceful getaway, our home offers high-speed Wi-Fi, a fully equipped kitchen, and cozy furnishings. Two bedrooms featuring superking beds, one with ensuite. Outside bbq area with comfy seating, firepit, dining area and hot tub. Whether you're here for a weekend escape or a longer stay, this house provides the perfect setting to relax and unwind.

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
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 *

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
4.95 out of 5 average rating, 542 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 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
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 favourite
Flat
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
4.99 out of 5 average rating, 86 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.

Guest favourite
Apartment
4.86 out of 5 average rating, 65 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.

Guest favourite
An outdoor deck features a wooden hot tub beside a mirrored house, surrounded by trees. Two wicker chairs are positioned on the deck, with a small table displaying refreshments. The scene reflects the lush greenery, creating a harmonious integration with nature.
Cabin
4.98 out of 5 average rating, 181 reviews

The Mirror Houses - Cubley

Our Mirror Houses are located in a remote area of a family-run farm near the Oxfordshire village of Kirtlington. They are hidden away in woodland in the grounds of the Kirtlington Park Polo Club, next to a Capability Brown-designed lake. Surrounded by stunning landscape and reflecting the trees and nature around them, the Mirror Houses offer a peaceful and idyllic retreat from city life.

Top guest favourite
Home
4.99 out of 5 average rating, 232 reviews

Fern at Church Farm Retreats - Luxury Country Stay

​Fern is a new stylishly furnished one bedroom unique and airy self-catered holiday retreat consisting of an open plan living room with kitchen, separate bedroom with king size bed and large 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

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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 £7 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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  5. Headington