Guesthouse vacation rentals in Headington

Find and book unique guesthouse rentals on Airbnb

Quick stats about guesthouse rentals in Headington

  • Total vacation rentals

    Explore 30 vacation rentals in Headington

  • Nightly prices starting at

    Headington vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Headington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Headington rentals

  • 4.6 Average rating

    Headington stays receive an average rating of 4.6 out of 5 from guests

Top-rated guesthouse rentals in Headington

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

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Top guest favorite
Guesthouse in Freeland
5 out of 5 average rating, 122 reviews

Quiet Annex: Woodstock Oxford & Cotswolds: Parking

Relax in a peaceful annex minutes from Blenheim Palace, Woodstock & Oxford close by. With countryside views, parking, complimentary breakfast provisions & underfloor heating, an ideal base for exploring or working. Private entrance, workspace/Wi-Fi. Sofa-bed not made up by default, advise in advance if needed. Estelle Manor, Woodstock/Blenheim Palace, Witney, Kidlington, Oxford all very close & easy travelling to Bicester Village, Diddly Squat Farmshop, The Farmers Dog and Cotswold villages.

Top guest favorite
A wrought iron gate is showcased with a sign reading 'The Annex.' The pathway leads towards a brick building with a white window, surrounded by well-kept grass. The area appears peaceful, emphasizing the cottage's inviting entrance.
Guesthouse in Holton
4.94 out of 5 average rating, 154 reviews

A self contained detached Annex in cottage garden

Chance Cottage Annex is a uniquely built and individual building located within the garden of a 18th Century Cottage. The Annex has been fully refurbished in April 2025 and returning to Airbnb after 2.5years. It has its own private entrance and is located in a quiet part of the pretty village of Holton, near Oxford. The village is just 2 miles from the M40 between High Wycombe and Oxford with easy transport links to Oxford city centre, London, the Midlands, Bicester Village and the Cotswolds.

Top guest favorite
A spacious living area features a grey sofa paired with plush cushions, arranged on a light-colored rug. Large glass doors provide views of the outdoor patio and garden. The modern kitchen includes sleek cabinetry and is equipped with essential appliances, ensuring a well-appointed space.
Guesthouse in Standlake
4.97 out of 5 average rating, 259 reviews

Idyllic village, gateway to the Cotswolds, nr pub

Beautiful village on the edge of the Cotswolds: - 1 minute walk to award winning gastro pub - 4 minute walk to shop/post office - 20 minute drive to historic university city of Oxford - 25 minute drive to Blenheim Palace Walk the Windrush Path from Standlake to Newbridge calling at: Standlake Common Nature Reserve, The Rose Revived &/or The Maybush Pub - leading to the Thames Path walk. Lovely, new Cherrytree Lodge has comfy beds and loads of amenities - walking distance to 4 great pubs!

Guest favorite
A view from the patio into the kitchen and living area reveals a bright, open space. A striped sofa adds comfort, accompanied by decorative cushions. Light wood cabinetry lines the walls, complemented by modern appliances. A textured rug covers the floor, enhancing the cozy atmosphere.
Guesthouse in Boars Hill
4.9 out of 5 average rating, 125 reviews

Oxford Country Cabin

A peaceful country setting just 10-15 minutes away from Oxford centre. Set in the unique & tranquil Boars Hill area, hidden down a quiet forest lane. Oxford station is a picturesque and quick 5.6km cycle or hike away through the Oxfordshire countryside. Surrounded by beautiful trails plus some wonderful pubs to enjoy such as the Farmers Dog just 30 mins away. A 1 bedroom cabin with a sofa bed, providing space for 4 guests plus a garden with outdoor dining. We hope you like our cabin!

Top guest favorite
A spacious bedroom is highlighted by wood-paneled walls and warm lighting. A large bed is adorned with soft linens, complemented by decorative pillows. A cozy seating area includes an armchair, while artwork and plants add character to the room. Soft rugs are placed on the wooden floor.
Guesthouse in Oxfordshire
4.97 out of 5 average rating, 609 reviews

The Hayloft - luxury country retreat

A country hideout above our detached oak framed barn. Stylishly furnished in a rustic luxury theme ensuring this retreat ticks all boxes to make your stay comfortable & cosy! Very spacious and an ideal place to come and relax for a romantic countryside break. Fantastic pub in the neighbouring village that serves food most days (please check) and there is a very well equipped kitchen should you like to cook for yourselves. Easy access to Oxfordshire best countryside walks too.

Guest favorite
A wooden post displays the number 47 in polished metal, with sunlight filtering through the surrounding greenery. The post is part of a rustic fence, contributing to a welcoming entrance.
Guesthouse in Cowley
4.92 out of 5 average rating, 110 reviews

The new auto house

The auto house is light, stylish and bijou , suitable for a single person working in oxford, or a weekend break for one or two people., simply furnished, with one king size bed, a table and two chairs, a small two seater sofa and a fridge, kettle and tea and coffee cupboard. Excellent access to oxford town centre, Oxfam, British Gas and oxford science parks and all the university’s and their surroundings. You can eat well locally in ox4, try the Magdalen arms gastro pub.

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
4.89 out of 5 average rating, 114 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
The charming brick exterior of the barn features a slate roof and arched windows. A gravel driveway leads to the entrance, flanked by decorative plants. Two seating areas are positioned outside, inviting relaxation in a serene garden setting.
Guesthouse in Worminghall
4.92 out of 5 average rating, 218 reviews

Charming barn conversion with vast living space

Set alongside our beloved family home, in 7 acres of open farmland, this wonderful space offers a welcome retreat from the stresses of everyday life. Worminghall is predominantly a farming village, within easy vehicular access to Oxford and the market town of Thame. Situated on the Oxfordshire/Buckinghamshire borders, it's the perfect location if you are visiting for a wedding or function nearby, or simply wish to explore the area's many local attractions.

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, 554 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 favorite
A comfortable lounge area is highlighted by a cozy velvet sofa in dark green, a low wooden coffee table with a decorative plant, and a flat-screen TV that displays the Netflix logo. Natural light enters through a large window with horizontal blinds.
Guesthouse in Holton
4.78 out of 5 average rating, 297 reviews

Pretty Oxfordshire Annexe

The Paddock Annexe is a detached, 2 storey apartment in the grounds of The Paddock House. It has one parking space and private entrance. It is located in the peaceful village of Holton, just 6 miles from the centre of Oxford. Oxford, High Wycombe and London are all easily accessible and there are lots of transport links nearby. This is a great location for the John Radcliffe Hospital, Oxford University and Oxford Brookes.

Guest favorite
A modern wooden annex features large glass windows that provide expansive views of the surrounding fields. A small outdoor seating arrangement is visible on a stone patio, complemented by greenery from nearby shrubs and trees.
Guesthouse in Long Hanborough
4.93 out of 5 average rating, 439 reviews

Entire Garden Annex with Breathtaking Views

Lovely self-contained annex with breath-taking views over the open fields. Open plan spacious living room and kitchen on the ground floor with a double bedroom with en-suite on the first floor. Short walk to Hanborough train station with great links into London, Oxford and the Cotswolds. Plenty of country walks, pubs and within walking distance to Blenheim Palace.

Guest favorite
A bright kitchen area features wooden walls and ceiling, creating a warm atmosphere. An extendable table with two chairs is positioned near a large window, inviting natural light. A television is mounted on the wall, while a compact kitchenette is visible beside a tall storage unit.
Guesthouse in Oxford
4.93 out of 5 average rating, 367 reviews

Beautiful garden cabin

Enjoy the tranquil view from this comfortable, well insulated chalet-style cabin. It has a separate entrance via the garden gate, and guests will be totally self-contained away from the house. This is an ideal resting place after exploring Oxford's historical centre. Full cooking facilities, fridge, shower room, tv and internet connection. Sleeps two.

Popular amenities for Headington guesthouse rentals

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