House holiday rentals in Chessington

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Top-rated house rentals in Chessington

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Top Guest favourite
A spacious living area features a comfortable sectional sofa adorned with colorful throw pillows. A light rug defines the seating space, while natural light filters through large windows. Minimalist decor elements, including a mounted antler and lanterns, add character to the neutral-toned walls.
Home in Englefield Green
4.97 out of 5 average rating, 138 reviews

Five Star Boutique House near Windsor Castle, Ascot & London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Top Guest favourite
The outdoor seating area features a rectangular table with a decorative flower arrangement, arranged on a light-colored tiled surface. In the background, large glass doors open to a stylish interior, revealing a modern kitchen and comfortable sofa.
Home in Greater London
4.94 out of 5 average rating, 127 reviews

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.

Superhost
An open-plan kitchen and dining area features a central island with a sleek countertop. Modern furnishings include a dining table with chairs, and large glass doors allow natural light to fill the space while providing views of the garden.
Home in Surrey
4.88 out of 5 average rating, 16 reviews

Modern 3 bed family home near Esher

Lovely family home available within walking distance to 2 mainline stations, Hinchley Wood & Esher, both are direct to Waterloo. Open-plan kitchen & dining room, perfect for cooking & sharing meals with family & friends. Upstairs are 2 large double bedrooms & a family bathroom, then up one more flight there's a large bedroom with a king bed and ensuite shower room. Large garden to relax in and get away from the hustle and bustle of life, ideal for families visiting as it's a home-away-from-home.

Top Guest favourite
An open plan kitchen with modern appliances is displayed, featuring a large stainless steel refrigerator and a central island with bar stools. Natural light floods the space through skylights and large glass doors, creating a bright atmosphere. Sleek tile flooring complements the design.
Home in Kingston upon Thames
4.98 out of 5 average rating, 59 reviews

Fabulous 5 Bed House in London Borough of Kingston

This is a beautifully decorated and luxurious 5 bed house in the historical market town of Kingston upon Thames. The local train station is a 10min walk and has direct routes to London, Wimbledon, Twickenham and Richmond, with Central London just a 30min ride. Kingston has an amazing shopping centre and a large range of fantastic restaurants, pubs, clubs and live music events. It is also a hub to Hampton Court Palace, 3 Royal Parks, Racecourses, Kew Gardens, and many other local attractions.

Top Guest favourite
Home in Surrey
4.97 out of 5 average rating, 30 reviews

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.

Guest favourite
The exterior of a charming brick house is showcased, featuring a mix of red brick and white detailing. Two distinct front doors are positioned symmetrically, with one door framed by an arched entrance. The sky above is clear, creating a bright backdrop.
Home in Dorking
4.86 out of 5 average rating, 132 reviews

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.

Top Guest favourite
A light-filled living area is furnished with a plush sofa and decorative pillows. A stylish coffee table sits centrally on a patterned rug. Lush plants add a touch of greenery, while a large television rests against a sleek media console, enhancing the inviting ambiance.
Home in Surrey
4.93 out of 5 average rating, 162 reviews

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.

Top Guest favourite
Home in Hampton
4.91 out of 5 average rating, 11 reviews

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.

Top Guest favourite
The open plan living area features gabled ceilings and stylish furnishings. A comfortable sofa sits across from a galley kitchen with modern cabinetry. French windows open to a private patio garden, while natural light enters through sheer curtains, creating a bright and inviting atmosphere.
Home in Molesey
5 out of 5 average rating, 134 reviews

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.

Top Guest favourite
The exterior of a spacious two-story house is captured, featuring a blend of textured cream and brick siding. A neatly landscaped front garden includes vibrant greenery. A driveway accommodates a parked vehicle, and a secure entrance with a decorative door is visible.
Home in Surrey
4.92 out of 5 average rating, 131 reviews

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.

Superhost
A dining area and living room are displayed in an open layout. A dark wooden table is set with colorful placemats, complemented by a bowl of fruits. A modern sofa and HD TV are visible in the background, illuminated by warm lighting from wall fixtures.
Home in Ewell
4.9 out of 5 average rating, 101 reviews

House near Epsom, ideal for business travelers

Ideal for business travelers, a 3 bed house in Ewell West. #Adults only #. Close to Epsom, Sutton, Kingston & Wimbledon. London 30 mins by train. Heathrow and Gatwick airports 30-40 mins. Epsom Racecourse 15 mins. Golf, Walking, Farms and other leisure activities nearby. * School zone no entry between 8-9am, 2.30-4pm*

Guest favourite
Home in Surrey
5 out of 5 average rating, 5 reviews

Stylish Home in the Heart of Cobham - Free Parking

Set on a quiet and desirable road off Cobham high street , this gorgeously newly renovated 4-bedroom home offers a bright, modern and stylish base just outside London. With free off-street parking, a private garden and flexible sleeping arrangements, it’s ideal for families, small groups or longer stays.

Popular amenities for Chessington house rentals

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 $43 AUD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chessington holiday rentals include Wi-Fi 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!

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