
House holiday rentals in Chessington
Find and book unique houses on Airbnb
Quick stats about house rentals in Chessington

Total holiday rentals
Explore 30 holiday rentals in Chessington

Nightly prices starting at
Chessington holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chessington holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chessington rentals

4.9 Average rating
Chessington stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Chessington
Guests agree: These houses are highly rated for location, cleanliness and more.

Unique Architect-Designed 3BR Home, London
Experience refined living in this architect-designed 3-bedroom stylist home, where contemporary design meets everyday comfort.Enjoy bright open-plan living, premium finishes, air-conditioned living areas, a fully equipped kitchen, luxurious bathrooms, and a private landscaped garden perfect for relaxing. Just a 5-minute walk to Chessington North station, with direct trains to Wimbledon (15 mins) and London Waterloo (30 mins). Minutes walk to Chessington World of Adventure, golf courses and more.
ValueLocationIndoor spaces

Film Studio*Heathrow Airport*Families*Long Stays
Outstanding Property with Excellent Reviews (4.95/5 from 164 Guests) Nestled in a picturesque area, this property offers a perfect balance of tranquillity & convenience. Enjoy a short stroll to the scenic canal, lush farmlands, and numerous attractive footpaths. Key amenities are just moments away, including Addlestone train station, GP services, a pharmacy, Tesco Extra, shops, and cozy cafés. Weybridge is also within walking distance. Discover the perfect stay at our highly-rated property
ValueFamilyRiver

The Nook
Kick back and relax in this calm, stylish space. This ground floor one bed apartment is perfect for romantic getaway with your partner, or if you are in town for work and you are looking for a home away from home. If you have a little one you want to bring with you. Victoria station is a 20 minute train away, as well as being 15 minutes away from Wimbledon and Croydon by tram. All house trained dogs of all sizes welcome. EV charging points are NOT on premise. They are on street charging points.
FamilyValueComfort

Tudor House
Tudor House is a newly refurbished 2 bedroom house, situated 1 minute walking distance to the world famous Epsom Downs Racecourse, home of the Epsom Derby. This delightful property has a spacious living room area, 1 downstairs WC, stylish kitchen and patio area. Upstairs you will find a comfortable double bed, wardrobes, TV and dressing table. The second bedroom consists of 2 single beds which can be made into a double, fitted wardrobe and TV. The upstairs bathroom has a bath and shower.
FamilyLocationQuiet

Stunning 4BR Kingston Oasis, Free Parking Nr Train
Enjoy a relaxing stay at this luxury 4-bedroom home in the heart of Kingston, featuring a lush tropical garden and stylish modern interiors. With bright open-plan living area, spacious bedrooms and a gorgeous kitchen this is a home away from home Fans available in each bedroom Free on-street parking by request Amazing location within 5 minutes walk of shops, cafes, parks and 11 minutes walk to Kingston Station, with fast links to central London. Ideal for families or professionals.
FamilyLocationIndoor spaces

Riverside Rustic Cottage (but not on an island ;0)
Tranquility in a busy world... Sit out and watch the river world go by in this haven of calm. With the rear garden running down to the River Thames itself, an ideal place to come back to after a busy day sightseeing (or working). In the beautiful village of Thames Ditton, complete with a wide range of restaurants, pubs, an Italian coffee shop, French bakery and other village stores but still with the trainline in to London. A great base or simply relax and unwind with the whole family.
FamilyLocationHeating

Hampton Court: Spacious, Bright & Tranquil Annexe
Our newly renovated spacious 2 bedroom annex is situated in a wide tree lined road, a premier location just a few minutes walk away from the charming cafés, shops and restaurants of Hampton Court Village, Hampton Court Palace and local train station. Adjacent to but detached from our elegant Victorian family home, this bright and stylish space is tranquil and self contained and enjoys additional benefits of a private south facing patio garden and dedicated off street parking space.
ValueFamilyAccuracy

Cheerful 5 bedroom house with off street parking
Bring the whole family to this great place with lots of room for fun. The house is very spacious with a good sized garden. Four double bedrooms and one single bedroom. Master suite with ensuite bathroom. Main bathroom and also shower room downstairs. Plenty of kitchen area with bar seating and also washing machine in separate annexe area. Excellent transport facilities nearby with both buses and trains. Very close to The Epsom Downs Racecourse. Excellent walking area.
FamilyValueWi-Fi

Welcome to The Cottage - Thames Ditton, Surrey
Relax with the family. A quaint 2 bedroom cottage in the heart of the historical village of Thames Ditton. With off street parking and a beautiful garden, you can enjoy a coffee on the patio or simply walk a minute to a selection of cafes, restaurants and village stores. A perfect place to start and end your day, whether it be sightseeing in London, going to the races, visiting Hampton Court Palace or nearby National Trust properties.
FamilyLocationWalkability

The Coach House, Halstead Hall
The Coach House, Halstead Hall is a cosy, detached cottage within the grounds of the Grade II listed residence of the esteemed author Edith Nesbitt. Located in the peaceful village of Halstead, this idyllic retreat offers tranquility while being conveniently just a 20-minute train journey from London, accessible via a short taxi or bus ride to the local train station.
LocationFamilyNearby

Idyllic House on the Thames
A tranquil escape for all seasons, experience a truly unique escape on an Island in the Thames, within easy reach of London. The Shack is a newly renovated and beautifully appointed early 20th century riverfront bungalow located on an exclusive Island in the Thames. Perfectly arranged for a weekend getaway, or an extended escape for some tranquillity and relaxation.
FamilyLocationCleanliness

2-bedroom riverside cottage in Surrey Hills
Charming and comfortable cottage in the heart of Surrey Hills. Recently renovated with discrete Smart technologies and new furnishings throughout, whilst preserving the character of this peaceful historic cottage. You will enjoy your own private stretch of riverbank on the Tillingbourne River.
LocationFamilyDecor
Popular amenities for Chessington house rentals
House rentals with a pool

Private Spa Suite with Refreshing 12m Indoor Pool
LocationAmenitiesCleanliness

Family home with pool
FamilyCleanlinessPool

Bright spacious home with natural swimming pond
LocationFamilyQuiet

Wellness Escape by River: Sauna, Pool, Hot Tub
ValueLocationKitchen

Amazing family house in London ideal for families
LocationFamilyParks

Little Rozel Retreat | Hot Tub, Swim Spa & Nature
LocationIndoor spacesWi-Fi

Surrey Cottage with indoor heated swimming pool
FamilyValueHospitality

Lux Riverside Flat In Battersea Power Station
LocationNearbyGetting around
Weekly house rentals

Spacious Family Bungalow with Garden for up to 7
FamilyValueWi-Fi

Spacious 4 bed Victorian cottage with parking.
ValueHospitalityOutdoor spaces

Wimbledon Village 3-Bed House | Free Parking
LocationFamilyNearby

Peaceful home, Surbiton -FreeParkings-No Guest Fee
ValueFamilyGetting around

The Stanley Modern 3/4BED 3BATH | Comfort & Style
FamilyLocationAccuracy

Luxury one-bed house centrally located
ValueLocationWalkability
High Street Apartment ESHER
ValueFamilyView

Historic Surrey Hills Cottage 30 mins from London
LocationFamilyTV
Private house rentals

Hampton Court Snug Sleeps 2-6 Walk to Palace+Train
LocationIndoor spacesNearby

Stunning Twickenham 3BR Retreat with Free Parking
FamilyLocationCleanliness

3 bedroom house with parking
FamilyLocationNearby

Little Burley
ValueLocationAmenities

Grand 4BR Home Near Heathrow Free Parking & Garden
LocationNearbyParking

Waterside retreat in the heart of Sussex
FamilyLocationTV

The Light & Luxe Haven
FamilyLocationLong stay

Cosy 2 Bed, Mews Cottage nr River
FamilyLocationCheckout
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- Brighton Seafront
- West Wittering Beach
- London Bridge
- St Pancras International
- ExCeL London
- The O2
- Tottenham Hotspur Stadium
- Emirates Stadium
- Tower Bridge
- Goodwood Motor Circuit
- Clapham Common
- University of Oxford
- South Downs National Park
- Thorpe Park Resort
- Chessington World of Adventures Resort
- Victoria Park
- LEGOLAND® Windsor Resort
- Buckingham Palace
- Big Ben





