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Chessington holiday homes

We found 2,429 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chessington that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you need and want for your stay, including air conditioning and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Chessington

Showing deals for:9 Oct - 16 Oct

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Why visit Chessington

  • Family-friendly attractions: Chessington boasts a variety of engaging activities perfect for families, ensuring fun for all ages.
  • Outdoor adventures: Experience the beauty of local parks and green spaces, ideal for relaxation and outdoor pursuits.
  • Historic landmarks: Explore the area's rich history through its charming historic houses and sites.
  • Cultural immersion: Enjoy the vibrant local scene, which reflects the welcoming spirit of the United Kingdom.
  • Charming neighbourhoods: Stroll through picturesque streets and discover hidden gems that enhance your stay.

Top attractions near Chessington

Chessington, England, offers a delightful mix of family-friendly attractions and outdoor adventures. Visitors can explore its urban parks, historic houses, and vibrant streets, perfect for immersing in local culture and enjoying fresh air. With a range of experiences tailored to families and those seeking adventure, Chessington provides an ideal setting for a memorable holiday, ensuring there's something for everyone to enjoy in this charming city.

  • Hampton Court Palace: A historic palace with rich cultural vibes, located 6km from the heart of Chessington, offering a glimpse into England's regal past.
  • Kensington High Street: A bustling street exuding city vibes, situated 19km from Chessington, perfect for immersing in urban life and vibrant retail scenes.
  • Thorpe Park: A thrilling theme park with entertainment and family vibes, positioned 16km from Chessington, promising exhilarating adventures for visitors.

Things to do recommended for couples

Looking for a romantic escape in Chessington? Enjoy a charming cableCarGondola ride at IFS Cloud Royal Docks Station, 29km away, or explore IFS Cloud Greenwich Peninsula Station, 27km away, perfect for adventurous couples seeking outdoor fun.

Things to do recommended for families

In Chessington, families can explore Chessington World of Adventures and get up close with animals at the zoo, all while enjoying the local charm and warm hospitality of England.

Things to do recommended for groups

Groups visiting Chessington can experience the thrill of motorsport at Mercedes-Benz World, just 11km away, and enjoy an adventurous day at Go Ape in Bracknell, a zipline ropes course located 31km from Chessington, perfect for outdoor fun.

*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 in Chessington

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, be sure to filter by the appropriate criteria. Here are some Vrbo booking tips for you.

  • Traveling to Chessington with a group: Consider the number of bedrooms required, along with features like a full kitchen or an outdoor area suitable for a group gathering. Luckily, you can easily filter for all these options, and more, on Vrbo.
  • Traveling to Chessington with young kids: Traveling with little ones comes with its challenges. You must prioritise their comfort and safety, ensuring the availability of age-appropriate facilities, like a private swimming pool. It’s also wise to factor in how close you are to attractions that cater to families.
  • Taking your pets with you to Chessington: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chessington: If you’re seeking holiday rentals offering special rates for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and secure savings on monthly rentals. You might also want to include a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Chessington

Discover Chessington, a captivating city perfect for family and adventure holidays, where charming neighbourhoods and vibrant local experiences await. Embrace the allure of outdoor adventures, explore local landmarks, and savour the friendly, relaxed atmosphere that reflects the spirit of the United Kingdom. Whether you're exploring hidden gems or enjoying the lively local scene, Chessington offers a delightful escape for all travellers, making it an ideal destination for a memorable holiday.

  • London: Located in the heart of Chessington’s sprawling metropolis, London offers a vibrant blend of family fun, city life and cultural escapades. Visitors can immerse themselves in a diverse array of experiences from bustling shopping areas and captivating theatres to dynamic arena entertainment. The area is dotted with iconic urban landmarks, expansive parks and lively tourist precincts that bring history and modernity together. London’s rich tapestry of attractions ensures every traveller finds something to delight in.
  • Epsom: Situated 3km away from Chessington, Epsom presents an inviting mix of family-friendly, outdoor and adventure experiences. Travellers can explore thrilling amusement parks, enjoy a round of golf on scenic courses, or discover the charm of nearby historic sites including theme parks, intriguing museums and a stately historic palace. Epsom’s unique blend of attractions offers a refreshing escape with plenty of opportunities for exploration.
  • Tolworth: Also 3km from Chessington, Tolworth is a neighbourhood that caters to family, outdoor and city-themed adventures. Here, visitors can enjoy the excitement of amusement parks, browse through modern shopping mall centres and relax in open-air spaces. The proximity to urban parks, engaging museums and vibrant theme parks means that Tolworth is a great spot for a day of exploration and cultural discovery.

Best time to go to Chessington

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.5°F (4.7°C)Light RainMostly CloudyModerately Low
February41.7°F (5.4°C)No Rain (Dry)Mostly CloudyAverage
March45.0°F (7.2°C)No Rain (Dry)Mostly CloudyAverage
April49.3°F (9.6°C)No Rain (Dry)Mostly SunnyModerately High
May54.9°F (12.7°C)Light RainMostly SunnyAverage
June60.8°F (16.0°C)Light RainMostly SunnyAverage
July64.6°F (18.1°C)Light RainMostly SunnyModerately High
August64.2°F (17.9°C)Light RainMostly SunnyModerately High
September60.1°F (15.6°C)No Rain (Dry)Mostly SunnyAverage
October54.3°F (12.4°C)Light RainMostly CloudyAverage
November47.1°F (8.4°C)Light RainMostly CloudyModerately Low
December43.0°F (6.1°C)Light RainMostly CloudyModerately Low

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental. We're here to help make your travel planning as smooth and rewarding as possible.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space for planning your journeys, allowing you to start fresh, continue where you paused, or simply organise your plans. You can easily view and manage your saved or booked properties, neatly sorted into Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Chessington

Enjoy the entertainment and other features of Chessington. Well known for its safari tours, restaurants and wildlife, this welcoming city won't disappoint. Big Ben and Piccadilly Circus are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Chessington

Are you hoping to discover top things to see and do while you're in the area? You'll be sure to enjoy Chessington for its swimming and taking an adventure tour. Venture out of your cosy holiday rental and check out everything that Chessington has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® Windsor (16.7 mi / 26.9 km)
  • Chessington World of Adventures (0.3 mi / 0.4 km)
  • Hobbledown (1.1 mi / 1.8 km)
  • Walton Heath Golf Club (5.6 mi / 9.1 km)
  • St George's Hill Golf Club (5.9 mi / 9.5 km)
  • Silvermere Golf Complex (6.1 mi / 9.8 km)

Exploring the natural features in Chessington

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Chessington is a great place to spend some time outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Hyde Park (12.7 mi / 20.4 km)
  • Leicester Square (13.7 mi / 22 km)
  • Hampton Court (4.1 mi / 6.5 km)
  • Bushy Park (4.4 mi / 7.1 km)
  • Painshill Park (5 mi / 8.1 km)
  • Box Hill (6.5 mi / 10.4 km)

Transport options to and around Chessington

The nearest airport is in Heathrow Airport (LHR), located 10.4 mi (16.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Gatwick Airport (LGW), which is 14.7 mi (23.7 km) away.

If you prefer train travel, make your way to Chessington South Station or Chessington North Station and explore the city from there.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chessington?
According to our research, studios are the most in-demand type of property in Chessington. But naturally, everyone's idea of an epic stay can differ. Bookabach has holiday homes of all shapes and sizes, and we'll help you discover the perfect fit for you.
How much does it cost to rent a holiday home in Chessington?
The average price for a holiday home in Chessington is based on several factors, including length of stay, property type and season. Whether you're in search of a villa with space for extended family or a cosy cottage perfect for just you and the kids, just add your travel dates to discover stays with exceptional value.
How much does it cost to rent a beach house in Chessington?
Prices for beach houses in Chessington vary depending on the style and size of the property and when you're travelling. All you have to do is enter your travel dates into Bookabach and the number of guests to view your options and prices. From there you can use our filters to tailor your search by ratings, amenities and more.
What are popular home amenities in Chessington?
A fridge and a microwave oven top the list of home amenities that people search for in Chessington. When you lock in a Bookabach holiday home, you'll have the place to yourself, which means you won't have to share your holiday with strangers.
What are the top attractions for families in Chessington?
Keep the kids entertained at these popular family-friendly attractions in Chessington:

  • Hampton Court Palace
  • Chessington World of Adventures
  • Morden Hall Park

How old do you have to be to rent a holiday home in Chessington?
The minimum required age is usually 16, 18 or 21. It can change across properties on Bookabach, so look at the rules of your chosen Chessington holiday home before booking your stay.
How long can I rent a holiday home in Chessington for?
It's really down to the Chessington property. To view all available options offering extended stays, just type your travel dates and number of guests into Bookabach's search page. You can look forward to having the whole place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and a yard where the kids can play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

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