
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.

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

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.

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.

Architect-Designed Luxury House, 3BR Chessington
Experience refined living in this architect-designed 3-bedroom home in Chessington. Featuring stunning modern interiors, high-end finishes, and light-filled living spaces, this luxury retreat offers the perfect blend of sophistication and comfort. Ideal for tennis lovers visiting Wimbledon , Skillion House is just a 5-minute walk from Chessington North station, with direct trains to Wimbledon in around 15 minutes. A peaceful and convenient base for enjoying the Wimbledon Tennis Championships

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.

Beautiful 3 Bedroom Cottage In Central Dorking
Welcome to our fantastic newly renovated 3 bedroom home located in Dorking. Beautifully presented throughout, this self catering home benefits from an open plan fully equipped kitchen / lounge / diner with patio doors leading out to the courtyard which has its own outdoor dining area, which is well lit and full of gorgeous foliage. Spread over 4 floors there are 3 bedrooms that can comfortably accommodate up to 5 guests and two stunning bathrooms, both equipped with shower, sink and toilet.

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.

Ty Bach
A cosy, clean, warm and light annexe with its own walled garden. Situated on a beautiful private road a short walk from the historic cobbled streets of Guildford town centre with its numerous boutique shops and quality independent restaurants. Ty Bach is on the edge of the beautiful Surrey Hills (a designated Area of Outstanding Natural Beauty) and the Rivey Wey. It is the perfect destination for walkers, mountain bikers and lovers of the outdoors. Dog walking and country pub heaven!

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.

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.

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

Blackham Farm

Bright spacious home with natural swimming pond

Kensington Pool & Piano | Unique 3BR w/ AC, Garden

Wellness Escape by River: Sauna, Pool, Hot Tub

Amazing family house in London ideal for families

Little Rozel Retreat | Hot Tub, Swim Spa & Nature

Stunning 4 bed Godalming home

Surrey Cottage with indoor heated swimming pool
Weekly house rentals

Spacious Family Bungalow with Garden for up to 7

Welcome to The Cottage - Thames Ditton, Surrey

A Cozy Home Away from Home

3 bedroom house with parking

Large 1870s House with Direct River View & Garden

A luxurious country retreat with Jacuzzi hot tub
High Street Apartment ESHER

Fabulous 5 Bed House in London Borough of Kingston
Private house rentals

2-Bed Wallington, Sleeps 6, Parking, Near LGW

Surrey Hills Studio, Private Entrance & Parking

Spacious, Stunning Twickenham Retreat Free Parking

Highfield Home Surbiton+FreeParkings-No Guest Fee

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

Spacious 3BR Home in West London with Parking

The White House Oxshott

Luxury one-bed house centrally located
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- Brighton Seafront
- The O2
- ExCeL London
- West Wittering Beach
- Emirates Stadium
- Tower Bridge
- Clapham Common
- Goodwood Motor Circuit
- University of Oxford
- Buckingham Palace
- Thorpe Park Resort
- Chessington World of Adventures Resort
- South Downs National Park
- Alexandra Palace
- London Stadium
- Big Ben
- Windsor Castle





