
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.

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.

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

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.

5 Bed Family & Contractor Stay| Parking | Sleeps 8
Spacious refurbished 5-bedroom home in Walton-on-Thames, ideal for contractors, professionals and families. Sleeps up to 9 with 3 king rooms (each King can be split into 2x singles), 1 double and 1 single, plus 2 en-suites, main bathroom and WC. Includes driveway parking for 3 vehicles, extra free on-street parking, EV charger, fast Wi-Fi, workspace, fully equipped kitchen, utility, comfortable living areas and large garden. Close to Walton/Hersham stations, shops, road links and project sites.

Taylour House - Historic, unique, yet modern
Welcome to our historic 'hidden gem' Taylour House built in 1468 for the Lord Mayor of London. Quiet yet town centre location with local amenities on your doorstep. Easy reach of Central London, (Edenbridge Town station 10 mins walk) Gatwick and Heathrow. Sleeps up to 10 guests. Private dining by prior arrangement. Perfect for a holiday, family gatherings, birthday celebrations and hen/stag and bridal parties. Full refurbishment carried out in 2023. Children and dogs very welcome.

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.

Virginia Water Family Getaway
Lambly Hill House – Holiday Rental in Virginia Water, Surrey Welcome to Lambly Hill House, a stylish and spacious 4-bedroom holiday rental in Virginia Water, Surrey. Perfect for families, golf visitors and business travellers, this beautifully renovated home offers modern comfort, peaceful surroundings and a private garden in one of Surrey’s most desirable locations. Located just a short walk from Virginia Water train station, Lambly Hill House provides easy connections to central London.

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.

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.

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.

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.

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.
Popular amenities for Chessington house rentals
House rentals with a pool

Surrey Cottage with indoor heated swimming pool

2BR Victorian cottage w/ Garden near Camden Mkt

Woodland Escape with Heated Pool

Wellness Escape by River: Sauna, Pool, Hot Tub

South Wing of Country House

Bright spacious home with natural swimming pond

Little Rozel Retreat | Hot Tub, Swim Spa & Nature

Lux Riverside Flat In Battersea Power Station
Weekly house rentals

Stunning 4BR Kingston Oasis, Free Parking Nr Train

Riverside Rustic Cottage (but not on an island ;0)

Cozy 3 Bedroom Terrace Cottage in Epsom

Spacious Family Bungalow with Garden for up to 7

Historic Surrey Hills Cottage 30 mins from London

A modern, quirky hideaway - great links to London

Surrey/London. Home for 6/8 people. Fibre WiFi.

Wimbledon Village 3-Bed House | Free Parking
Private house rentals

Spacious 4 bed Victorian cottage with parking.
High Street Apartment ESHER

Fabulous 5 Bed House in London Borough of Kingston

3 bedroom house with parking

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

Stunning Twickenham 3BR Retreat with Free Parking

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

Waterside retreat in the heart of Sussex
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





