
Guesthouse vacation rentals in Headington
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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

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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.

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.

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.

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!

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!

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.

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.

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.

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.

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.

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.

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.

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
Family-friendly guest house rentals

Private Studio, in the Oxfordshire countryside

A one / two bedroom annexe in a village location

A charming self- contained Guest House near Oxford

Stylish country converted barn

Beautiful Grade II listed Guest House

Cotswold Barn near The Bull, Farmhouse & Clarkson

Harwell, self contained cottage

Castle Loft, Central Wallingford
Guest house rentals with a patio

Detached Cottage Near JR Hospital + Parking

Bungalow with Hot Tub in Oxfordshire

Iffley Hideaway Studio Cozy & Quiet Oxford Stay

Cosy Cotswold Stone Cottage

Cosy 1 bed annexe in Woodstock

Modern one bedroom self contained pod

Summer House on the Edge of the Cotswolds

Charming 2-Bed Guest suite Oxford
Guest house rentals with a washer and dryer

Oxfordshire Country Cottage

Charming Charlbury Cottage set in Idyllic garden

Peaceful Garden House in Oxford

The Abbey Garden Lodge

Destiny - Bohemian Haven

Luxurious & private annex in Cotswold village

Adorable Countryside Guest Annex

Double bedroom in Coachhouse Annexe
When is the best time to visit Headington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 419 | ﺩ.ﺇ 452 | ﺩ.ﺇ 452 | ﺩ.ﺇ 397 | ﺩ.ﺇ 393 | ﺩ.ﺇ 411 | ﺩ.ﺇ 433 | ﺩ.ﺇ 422 | ﺩ.ﺇ 430 | ﺩ.ﺇ 411 | ﺩ.ﺇ 382 | ﺩ.ﺇ 386 |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Destinations to explore
- Rentals with a patio Headington
- Rentals with breakfast Headington
- Smoking-friendly rentals Headington
- Bed and breakfasts Headington
- Pet-friendly rentals Headington
- Townhouse rentals Headington
- Serviced apartment rentals Headington
- Rentals with a hot tub Headington
- Apartment rentals Headington
- Condo rentals Headington
- Rentals with a fireplace Headington
- Family-friendly rentals Headington
- Rentals with an EV charger Headington
- Rentals with a fire pit Headington
- House rentals Headington
- Rentals with lake access Headington
- Rentals with a washer and dryer Headington
- Rentals with outdoor seating Headington
- Guesthouse rentals Oxfordshire
- Guesthouse rentals England
- Guesthouse rentals United Kingdom
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- Emirates Stadium
- Silverstone Circuit
- Cotswolds AONB
- Clapham Common
- University of Oxford
- Buckingham Palace
- Thorpe Park Resort
- Stonehenge
- Blenheim Palace
- Chessington World of Adventures Resort
- Alexandra Palace
- Big Ben
- Windsor Castle
- LEGOLAND® Windsor Resort
- British Museum
- London Eye
- Primrose Hill
- Lower Mill Estate




