Headington holiday homes

We found 137 holiday rentals — enter your dates for availability

Discover a selection of 17 homes, 21 apartments and other holiday rentals in Headington that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include a pool and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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  • All the privacy of home

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  • More for less

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Why visit Headington

  • Quaint charm: Stroll through Headington's picturesque streets, filled with historic buildings and local shops.
  • Iconic attractions: Visit the famous Headington Shark, a quirky landmark that captures the area's unique spirit.
  • Beautiful parks: Enjoy the lush greenery of Headington Hill Park, perfect for picnics and leisurely walks.
  • Rich history: Discover the fascinating heritage of the universities nearby, blending the old with the new.
  • Friendly locals: Experience the welcoming atmosphere and engage with the friendly community.

Top attractions near Headington

Headington offers a delightful mix of culture, history, and family-friendly activities, making it a great spot for a getaway. You can explore the historic and modern universities, visit the iconic Headington Shark, and enjoy the lush surroundings of Headington Hill Park. Don't miss the chance to wander through the city of Oxford and discover hidden gems in Headington that cater to all travellers seeking a unique experience.

  • University of Oxford: A prestigious institution steeped in history, featuring stunning architecture and vibrant culture just 3.2km from Headington. Explore its picturesque courtyards and soak in the academic atmosphere.
  • Christ Church College: This iconic college, located 4.8km away, combines breathtaking architecture with a rich history. It's also famous for its connections to Harry Potter, offering a unique cultural experience.
  • Bodleian Library: One of the oldest libraries in Europe, situated 3.2km from Headington, this treasure trove of knowledge provides a family-friendly experience, showcasing remarkable collections and historic reading rooms.

Things to do recommended for couples

If you're after a romantic getaway in Headington, explore the charming Brightwell Vineyard or Hundred Hills, both offering delightful experiences just a short drive away. For a unique twist, visit Daws Hill Vineyard, where you can enjoy the beautiful surroundings and sample exquisite wines together.

Things to do recommended for families

Families can unwind at Port Meadow, perfect for relaxation, or catch a match at Kassam Stadium for some sports excitement. For a bit of adventure, the Oxford Ice Rink offers a fun ice skating experience, making it a great outing for everyone.

Things to do recommended for groups

Catch a show at the New Theatre Oxford for a dose of culture and entertainment, explore the scenic Thames Path for a bit of adventure, or browse the unique stalls at the Covered Market for a taste of local city life—all within a stone's throw from Headington.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Headington

If you're heading off on an adventure with friends, family, or even your furry companions, or if you're planning an extended getaway, it's important to sort your options according to what matters most to you. Here are some helpful tips for booking on Vrbo.

  • Traveling to Headington with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Headington with young kids: Travelling with young kids can be a bit tricky. It's important to prioritise their comfort and safety, along with having suitable facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Headington: For many families, a getaway wouldn't be the same without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Headington: If you're in search of holiday rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Headington

Headington, a charming suburb of Oxford, offers a delightful mix of culture, history, and friendly locals. Explore its scenic parks and historic sites, or venture into nearby Oxford for a taste of urban life. Perfect for family trips or relaxed getaways, Headington provides a unique atmosphere where you can unwind and soak in the rich heritage. Whether you're wandering through quaint streets or enjoying local cafes, there's something for everyone in this lovely area.

  • Oxford: Nestled in the heart of England, Oxford is a city renowned for its prestigious university and rich history. Just a stone's throw from Headington, this vibrant city is perfect for those seeking a cultural and family-themed experience. Here, you can explore historic colleges, majestic monuments, and even a historic palace. The bustling shopping centres and malls offer plenty of retail therapy, making it a great spot for a day out with the family. Be sure to enjoy a leisurely stroll along the picturesque streets, soaking in the academic atmosphere that has inspired countless scholars.
  • Oxford City Centre: Located a mere 3.2km from Headington, Oxford City Centre is the beating heart of the city, attracting visitors with its lively atmosphere and cultural offerings. This neighbourhood is ideal for family outings and provides a wealth of educational opportunities, along with a variety of shopping areas and malls. Discover the historic colleges and charming streets, where you can appreciate the city’s architectural beauty. The City Centre is also home to numerous monuments and cultural venues, making it a must-visit for anyone looking to experience the essence of Oxford.
  • Cowley: Just 3.2km from Headington, Cowley is a lively neighbourhood that combines family-friendly activities with outdoor adventures. This area is perfect for those who enjoy theatre and entertainment, with various venues showcasing local talent. Cowley is also home to a stadium and sports facilities, ideal for catching a match or participating in outdoor activities. With its close proximity to the historic college university, Cowley offers a unique blend of culture and recreation, making it a fantastic place to explore during your visit.

Best time to go to Headington

If you're planning a trip to Headington, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.8°F (3.8°C)Light RainMostly CloudyAverage
February40.1°F (4.5°C)No Rain (Dry)Mostly CloudyAverage
March43.0°F (6.1°C)No Rain (Dry)Mostly CloudyAverage
April46.9°F (8.3°C)No Rain (Dry)Mostly CloudyAverage
May52.5°F (11.4°C)Light RainMostly CloudyAverage
June58.3°F (14.6°C)Light RainMostly CloudySlightly High
July62.2°F (16.8°C)Light RainMostly CloudySlightly High
August61.5°F (16.4°C)Light RainMostly CloudyAverage
September57.6°F (14.2°C)No Rain (Dry)Mostly SunnySlightly High
October52.0°F (11.1°C)Light RainMostly CloudySlightly Low
November45.1°F (7.3°C)Light RainMostly CloudySlightly Low
December41.2°F (5.1°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your existing itineraries, or manage your bookings with ease. You’ll find your saved or reserved properties neatly organised into Potential, Upcoming, or Current Trips. To dive into Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Headington?
Houses are the most popular type of holiday home in Headington, according to our data. Even if you have something else in mind, Bookabach has holiday homes in all shapes and sizes. Look over our options to find your perfect pad.
How much does it cost to rent a holiday home in Headington?
The average price for a holiday home in Headington depends on a number of factors, including season, property type and length of stay. Whether you're searching for a sprawling villa with space for the whole family or a cosy cottage perfect for just you and the kids, just enter your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Headington?
The average price for a holiday home close to the beach in Headington will depend on when you'll be there and the size and style of property you want. Find prices quickly and easily on Bookabach by entering the dates you'll be travelling. Then use our filters to select the number of bedrooms and amenities that you prefer, like air conditioning, a pool and WiFi.
Are there pet-friendly holiday homes in Headington?
Pack a squeezy toy and a bone for the pup in your life because Headington has 21 properties that roll out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check our "Pets allowed" filter box.
What are popular home amenities in Headington?
Tennis, a swimming pool and a garden top the list of most popular home amenities in Headington. Whether you're planning to travel by yourself, with your other half or a bunch of friends, Bookabach will help you find a holiday home that suits your tastes with a load of extras you'll love.
Are there large group holiday homes in Headington?
Yes, you'll find 10 holiday properties in Headington that can host five or more guests. From family trips to events like a friend's birthday, these stays have ample space to hang out with the people you love.
Are there holiday homes in Headington that welcome kids?
Gather the whole crew for an unforgettable adventure in Headington at one of our 21 family-friendly holiday homes. These stays offer conveniences that are great for getaways with the little ones, like dining rooms, living rooms and private pools. Just check the "Properties good for families" filter box and choose your favourite.
What are the top attractions for families in Headington?
Keeping the kids happy during your Headington holiday is a snap with these exciting family-friendly attractions:

  • Oxford Castle
  • Ashmolean Museum
  • Museum of the History of Science

Are there one-bedroom holiday homes in Headington?
You can choose from three one-bedroom homes in Headington. Whether you're looking for an apartment or a condo, Bookabach's one-bedroom properties are ideal if you don't require tons of space. One of the best parts about having your own pad? You won't ever have to share your getaway with strangers.
Can I find two-bedroom holiday homes in Headington?
Gather your nearest and dearest and experience complete comfort and privacy in one of the 10 two-bedroom holiday homes Headington has to offer.
Are there holiday homes with WiFi in Headington?
You can choose from nine holiday homes with WiFi in Headington. If you want to disconnect from daily life during your escape, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Headington?
The minimum age allowed can differ across properties on Bookabach, so be sure to look at the rules of the holiday home in Headington you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Headington for?
The amount of time you can rent a Headington holiday home for varies depending on the property. Simply enter your dates of travel to see available options offering longer term stays. They have all you need to make your extended getaway more enjoyable and comfortable, like kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.

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