
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 $52 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

Architect-Designed Luxury House, 3BR Chessington
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). Hampton Court, great golf courses and family attractions are nearby.

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.

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.

Surrey/London. Home for 6/8 people. Fibre WiFi.
A lovely Edwardian period with original features that accommodates 6 and can accommodate 8 on request. A ten minute walk to Epsom town centre, you will find shops and restaurants including Waitrose, Gails, Costa, Oliver Bonas, Caballo Lounge, The Picture House, a cinema and a leisure centre. Epsom train station (8-10 mins walk) gets you to London Waterloo in 35 minutes and areas to the south too. The town has numerous bus routes which end in Croydon, Sutton, Morden and Kingston.

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.

Cozy 3 Bedroom Terrace Cottage in Epsom
Welcome to your Ozzy Cozy Stays home away from home! 3 bed cottage style house, beautifully situated in the peaceful part of Epsom and moments from open woodland. The city centre and station are a 24 minute walk away, offering convenient 30 minute train links to London. The house comfortably accommodates up to 7 guests and features contemporary living space with 2 reception rooms, a fully equipped kitchen, 2 bathrooms, and 1 cloakroom.

Orquidea Relaxation home with hot tub
Come and enjoy this peaceful time to disconnect and live a few days of relaxation. This beautiful place is newly renovated and equipped with all the amenities you need to have the best stay, with the hot tub available for you to use at all time all year round.
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

Twilight Retro Haven + Hot Tub + Garden Cinema

South Wing of Country House

Old Wharf Cottage

Wellness Escape by River: Sauna, Pool, Hot Tub

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

Welcome to The Cottage - Thames Ditton, Surrey

Stunning 4BR Kingston Oasis, Free Parking Nr Train

Modern House in Hampton Hill

A luxurious country retreat with Jacuzzi hot tub

Wonderful family home

Luxury one-bed house centrally located

A Cozy Home Away from Home

Bell House Wimbledon | Stylish 3BR with Parking
Private house rentals

Blossom House New 3bed house in Barons Court

Grand 4BR Home Near Heathrow Free Parking & Garden

Cosy 2 Bed, Mews Cottage nr River

15th-Century Thatched Cottage on 2.5 Acres

Spacious, Stunning Twickenham Retreat Free Parking

A modern, quirky hideaway - great links to London

Modern 3 bed family home near Esher

Charming 2 bed cottage.
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
- Thorpe Park Resort
- Buckingham Palace
- Chessington World of Adventures Resort
- Alexandra Palace
- South Downs National Park
- London Stadium
- Big Ben
- Victoria Park





