
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.

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.
FamilyValueDecor
4.94 out of 5 average rating, 159 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!
ValueLocationAccuracy
4.97 out of 5 average rating, 269 reviews
Peaceful Garden House in Oxford
The Garden House is a brand new private one-bedroom property located in a charming Oxfordshire village 15 mins drive from the centre of Oxford and 20 mins from Bicester Village and Blenheim Palace. The space is set up for a fantastic night's sleep with a comfortable king-size bed and a quiet location. The only sound you will hear is wildlife. The property has a bright and breezy feel created by large glazed doors and high vaulted ceilings. Ultra-fast broadband makes it perfect for working.
LocationFamilyLayout
4.94 out of 5 average rating, 101 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!
FamilyValueAmenities
4.88 out of 5 average rating, 144 reviews
Stylish Countryside Guesthouse near Oxford
Immaculate and newly renovated guesthouse located in the stunning Oxfordshire countryside, surrounded by excellent walks and top quality restaurants/pubs. This beautiful light and bright space has everything you would ever need! Oxford, Bicester Village, Blenheim Palace & Waddesdon Manor are all within 20 mins, so you're in a perfect position to enjoy the scenery with a great range of things to do nearby. * Host My House manages this property which is owned by Sarah & Alastair Paterson *
ValueFamilyDecor
4.95 out of 5 average rating, 367 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.
LocationFamilyKitchen
4.97 out of 5 average rating, 643 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.
ValueLocationAccuracy
4.9 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.
ValueLocationBiking
4.87 out of 5 average rating, 126 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.
LocationFamilyBiking
4.92 out of 5 average rating, 226 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.
FamilyValueHeating
4.95 out of 5 average rating, 581 reviews
Private Garden Cottage in Oxfordshire
Take it easy at this tranquil getaway in the ancient village of Horspath in the heart of the stunning Oxfordshire countryside. The Garden Cottage is set privately away from the main home with its own entrance, and offers free parking and a clean and warm space to relax. Only 6 miles from Oxford city centre, you are just a few minutes walk to the village bus service, local country pub, restaurants, brewery, shop and shotover national forest.
FamilyLocationCleanliness
5.0 out of 5 average rating, 106 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.
ValueLocationCondition
4.77 out of 5 average rating, 312 reviewsPopular amenities for Headington guesthouse rentals
Family-friendly guest house rentals

Adorable 2 bedroom property in Bucks countryside
FamilyLocationNearby
4.9 out of 5 average rating, 236 reviews
Private Studio, in the Oxfordshire countryside
LocationFamilyLayout
4.97 out of 5 average rating, 199 reviews
Private, self-contained annex suite near Woodstock
LocationValueWifi
4.88 out of 5 average rating, 420 reviews
Beautiful Grade II listed Guest House
LocationFamilyKitchen
4.93 out of 5 average rating, 164 reviews
Hoarstone - Cosy country cottage
LocationFamilyDecor
4.94 out of 5 average rating, 142 reviews
Comfortable cabin in our quiet garden
FamilyValueComfort
4.99 out of 5 average rating, 159 reviews
The Stables, Middle Barton
ValueLocationBreakfast
4.87 out of 5 average rating, 182 reviews
Castle Loft, Central Wallingford
LocationValueHospitality
4.97 out of 5 average rating, 138 reviewsGuest house rentals with a patio

Garden Hideaway (Parking&Pets friendly) - 牛津花园小栖
FamilyLocationOutdoor spaces
4.86 out of 5 average rating, 88 reviews
Iffley Hideaway Studio Cozy & Quiet Oxford Stay
ValueLocationLaundry
4.9 out of 5 average rating, 30 reviews
The Nook - Cosy, Modern Annexe
LocationFamilyCheck-in
5.0 out of 5 average rating, 96 reviews
Bungalow with Hot Tub near Bicester Village
FamilyLocationCheck-in
4.67 out of 5 average rating, 54 reviews
Charming 2-Bed Guest suite Oxford
FamilyLocationHospitality
5.0 out of 5 average rating, 7 reviews
Cosy 1 bed annexe in Woodstock
ValueFamilyNearby
4.94 out of 5 average rating, 78 reviews
Cosy Stone Barn Annex w/ Footpath Access
ValueFamilyKitchen
4.82 out of 5 average rating, 76 reviews
Lovely self-contained annexe in Oxfordshire
FamilyValueLong stay
4.97 out of 5 average rating, 59 reviewsGuest house rentals with a washer and dryer

Quiet Annex: Woodstock Oxford & Cotswolds: Parking
FamilyValueLong stay
5.0 out of 5 average rating, 126 reviews
The Post Office Barn Chalgrove
ValueLocationBreakfast
4.96 out of 5 average rating, 522 reviews
Spacious private ensuite, superb views near Oxford
FamilyLocationBiking
4.94 out of 5 average rating, 289 reviews
Charming Charlbury Cottage set in Idyllic garden
FamilyLocationHospitality
4.93 out of 5 average rating, 434 reviews
Oxfordshire Country Cottage
FamilyLocationCondition
4.96 out of 5 average rating, 148 reviews
Luxurious & private annex in Cotswold village
ValueFamilyAmenities
4.95 out of 5 average rating, 150 reviews
Adorable Countryside Guest Annex
FamilyLocationBathroom
5.0 out of 5 average rating, 43 reviews
The Abbey Garden Lodge
LocationValueCleanliness
4.93 out of 5 average rating, 59 reviewsWhen 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 466 | ﺩ.ﺇ 470 | ﺩ.ﺇ 470 | 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 breakfast Headington
- Bed and breakfasts Headington
- Pet-friendly rentals Headington
- Rentals with a hot tub Headington
- Townhouse rentals Headington
- Serviced apartment rentals Headington
- Condo rentals Headington
- Apartment rentals Headington
- Family-friendly rentals Headington
- House rentals Headington
- Rentals with lake access Headington
- Guesthouse rentals Oxfordshire
- Guesthouse rentals England
- Guesthouse rentals United Kingdom
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- Silverstone Circuit
- Clapham Common
- Cotswolds AONB
- Emirates Stadium
- Thorpe Park Resort
- University of Oxford
- The National Bowl
- Tottenham Hotspur Stadium
- Blenheim Palace
- Big Ben
- Buckingham Palace
- Stonehenge
- Alexandra Palace
- London Eye
- British Museum
- Windsor Castle
- LEGOLAND® Windsor Resort
- Regent's Park




