
House holiday rentals in Chessington
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Top-rated house rentals in Chessington
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Country Modern House - 5 bedrooms
Welcome to Belton Acre, a large stylish house with ample parking is nestled between the Surrey Hills and South Downs. The beautiful countryside offers fantastic walking, cycling (road and mountain trails), kayaking and fishing. The house is perfect for families, weddings, business trips and wellness retreats. There are four double bedrooms and a twin room. The house has been designed to be highly accessible for wheel chair users with a ground floor bedroom with ensuite adapted wet room.

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.

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.

Stylish 2BR | Sleeps 6 | Free Parking | Fast WiFi
Well-located 2-bedroom home in Thames Ditton with parking, fast WiFi and easy self check-in — ideal for contractors, relocations, hospital visitors and guests visiting Kingston, Hampton Court or Shepperton Studios. With direct rail access to London Waterloo, it’s a convenient and comfortable base for both short and longer stays. The dining table doubles as a practical workspace with nearby power outlets, and a second workspace can be arranged on request at no extra charge.

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.

Modern 1-Bed Self-Catering Home, Zone 6 London
Enjoy a stylish experience at this centrally-located home. This is a modern and tastefully designed self contained home, comes with a double bedroom with en-suite bathroom, fully equipped kitchen, utility room, garden and living-room with own driveway for free parking. 2 mins walk to West Ewell station from the property and it is only 35mins by train to London Waterloo It is I’deal for tourists, friends, business travellers or contractors

Racecourse Marina Lodge | Hot tub | Parking | EV
Live your high life on Windsor Racecourse Marina! Discover your dream get away with this beautifully designed luxury lodge located in a prestigious gated community. This property is perfect for a couple or a family looking to enjoy a relaxing luxurious lifestyle in tranquillity and peace. With amazing views over Windsor Racecourse and the boats moored on the marina, every moment here is a picture of calm elegance.

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.
Popular amenities for house rentals in Chessington
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

Large Island Home with Pool on the River Thames

Old Wharf Cottage

Serene and private double ensuite overlooking pond

Surrey Cottage with indoor heated swimming pool
Weekly house rentals

Detached 6 bedroom family house with Sky TV

Brand New Family House

3 bedroom house with parking

Charming 4-bedroom bungalow in Ashford, Surrey

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

Family home near Hampton Court (Sleeps 8)

3 Dbl Bed House Nr Hampton Court. Free Parking

House near Epsom, ideal for business travelers
Private house rentals

4 Bedroom Luxury Home Features HotTub & Pool Table

High end luxury home with Hot Tub | Parking, EV

Waterside retreat in the heart of Sussex

The White House Oxshott

Spacious 3BR Home in West London with Parking

Large Comfy 4BR, Ideal for Workers, FREE Parking

4 bedroom family home in Walthamstow E17

Lovely & Charming London House with Parking
Quick stats about house rentals in Chessington

Total holiday rentals
Explore 20 holiday rentals in Chessington

Nightly prices starting at
Chessington holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 300 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chessington holiday rentals include wifi access

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

4.8 Average rating
Chessington stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- South Downs National Park
- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- Kings Cross
- The O2
- Buckingham Palace
- Marble Arch
- Wembley Stadium
- Tottenham Court Road
- Tower Bridge
- London Bridge
- Big Ben
- Trafalgar Square
- Emirates Stadium
- ExCeL London
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common





