House vacation rentals in Chessington

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Top-rated house rentals in Chessington

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Guest favorite

The exterior features a charming two-story house set against a clear sky, with a spacious stone-paved driveway lined with greenery. Inside, a bright living area is depicted with large windows and modern furnishings, while the backyard showcases a neatly enclosed garden with grass and trees.

Home in Addlestone

4.94 out of 5 average rating, 104 reviews

Legoland * HeathrowAirport * Families * Long Stays

Outstanding Property with Excellent Reviews (4.94/5 from 132 Guests) Nestled in a picturesque area, this property offers a perfect balance of tranquility & 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!

Superhost

A classic two-story home is depicted, featuring a light grey exterior and distinctive windows that allow ample natural light. A gravel driveway leads to the main entrance, flanked by wall-mounted outdoor lights. The adjacent house appears in the background, providing a sense of neighborhood.

Home in Greater London

4.75 out of 5 average rating, 16 reviews

Wonderful family home

Experience the ultimate family retreat, conveniently located just 30 minutes from the vibrant city of London. Dive into adventure at Chessington World of Adventures, just 8 minutes away by bus, or unwind in the adjacent public playground. Enjoy the convenience of local shops within a 5-minute stroll. Our cozy home welcomes you with free Wi-Fi, driveway parking, and a private garden in the sun. Book now and create cherished memories with your loved ones in this haven of relaxation and excitement!

Superhost

A private outdoor patio area is shown, featuring wooden chairs with cushions surrounding a table. The ceiling is constructed of natural wood, and greenery is visible in the background, providing a serene view of the meadow garden.

Home in Seer Green

4.81 out of 5 average rating, 168 reviews

Modern Eco-Annex set within Meadow

We would love to welcome you to stay in our peaceful and modern self-contained property set with 1.6 acres of meadow garden. The house has been designed to make the most of the natural light and surroundings. The property is adjacent to the main house, is completely detached, and is separated by a large courtyard ensuring guests have complete privacy. A perfect place to escape into nature, visit historic towns and villages, or base yourself to work remotely with easy access to central London.

Guest favorite

A modern summerhouse is depicted with bifolding glass doors open to the garden. Inside, a well-equipped kitchen is visible along with a sitting area featuring a Smart TV. The space is brightly lit, with neutral-colored walls and a streamlined design.

Home in Greater London

4.96 out of 5 average rating, 106 reviews

Garden Summerhouse w/ Parking

Private garden summerhouse with full bathroom and kitchen at the back of our garden. The summerhouse is newly built, has full bifolding glass doors and it includes a Smart TV with Utra Fast WIFI. Our house is 5-minute walk from the heart of Wimbledon City Centre and Wimbledon train, tube, and tram station. There is a wide variety of restaurants, shops and supermarkets in the area. The property is tucked away in a quite road and has a modern garden with a beautiful mature cherry tree.

Top guest favorite

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, 115 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.

Guest favorite

A well-appointed bedroom features a spacious bed with decorative pillows and a soft blanket draping over it. Natural light fills the room through a large window adorned with greenery. Two bedside lamps are positioned beside a modern nightstand.

Home in Greater London

4.94 out of 5 average rating, 67 reviews

New Malden Studio

Delightful self contained studio near New Malden station, perfect for couples, business travellers and those visiting friends and family. This space offers its own bathroom, kitchenette, own side entrance, plus garden access. It is ideally situated with excellent transport links to central London and Gatwick + Heathrow airport. In addition it is conveniently located for those attending the Wimbledon tennis championships - enjoy a comfortable stay with all the essentials you need.

Guest favorite

The eco-friendly guest house is featured with a wooden facade, reflecting the blue sky. The view showcases a serene swimming pool, bordered by landscaped greenery, offering a tranquil outdoor space for relaxation.

Home in Cowfold

4.92 out of 5 average rating, 189 reviews

Large pristine 17m heated pool, countryside views

Unique eco sustainable guest house built in 2022 with stunning views over private fields lined with Oak Trees as well as views overlooking a private new pristine 17m swimming pool, heated from 1st April to Sept end 2025, (pool open Oct-Mar but not heated). Quiet location, country walks (close to National Park) and a local pub 1 mile away. Modern, new stylish interiors with a cosy wood burner and large patio and fire pit outside. Conveniently located 15 miles to Gatwick Airport.

Guest favorite

A modern dining area is highlighted by a round glass table surrounded by two gray chairs and one black chair. A decorative centerpiece rests on the table. A large artwork depicting a pier hangs on the wall, complemented by a wall clock and a gray sofa.

Home in Greater London

4.86 out of 5 average rating, 132 reviews

Cosy private home near Heathrow & Central London

Lovely bright 2 bedroom house in Hampton Hill near Heathrow & Central London. The property is located with a benefits from easy access to the motorway and as well key routs into central London is you wish to drive. With a short 7-10 minute by bus to the Feltham train station and the line is takes you to London Waterloo or Windsor Castle (a 25 minute journey) 15 minutes drive from London Heathrow Airport and 5-10 minutes drive to the Twickenham Rugby Stadium.

Top guest favorite

The image shows the entrance of a brick cottage, featuring a wooden door and a small step leading to it. A picket fence borders the grassy front yard, which is well-maintained. A planter with flowers is visible near the door, complementing the home's inviting exterior.

Home in Molesey

4.98 out of 5 average rating, 110 reviews

Lovely bright 2 bed home close to Hampton Court

We are situated just half a mile from Hampton Court where you will find an array of restaurants, cafes and shops to peruse and just a three minute walk from a large open park leading down to the River Thames. However, please note - Hampton Court is not in London and if you want to be close to London we may be too far for you. There is railway station which is about a 10 - 15 minute walk away and the line takes you to London Waterloo (a 35 minute journey).

Top guest favorite

The open-plan sitting area features a comfortable grey sofa adorned with decorative cushions. A wooden table sits in front of the sofa, accompanied by a cozy armchair and a side table. Natural light enters through the French doors, which lead to the garden.

Home in Kirdford

4.99 out of 5 average rating, 159 reviews

Country Retreat, The Old Cowshed - Sussex

Rural retreat near the South Downs – escape to The Old Cowshed, a cosy, private hideaway just over an hour from London. Tucked away at the end of a long farm drive, on the edge of the South Downs National Park, it offers a true “get away from it all” experience. Surrounded by nature and wildlife, with miles of walking trails on your doorstep, it’s ideal for couples (and a young child) looking to unwind. There’s scope to do as little or as much as you like!

Guest favorite

The Garden House is softly illuminated at night, showcasing a light-colored exterior that contrasts with the dark surroundings. A walkway leads to large glass doors, framed by lush greenery and trees, emphasizing the connection to nature in a private setting.

Home in Tolworth

5 out of 5 average rating, 7 reviews

Self-contained Garden Studio

Newly-built Garden House / Studio with en-suite and kitchen. Locked garden gate for private access and shared use of garden with outdoor dining area, bistro table. It has a kitchen with fridge, microwave, oven, hob, toaster & kettle. This fully insulated suite has Air-Con, heaters, a large shower, Smart TV, WiFi, working/eating space, with free on street and off street parkings.

Guest favorite

A well-lit bedroom features a spacious bed with soft pillows and decorative cushions. Light-filtering shutters cover the window, allowing gentle daylight to illuminate the space. A sleek nightstand stands beside the bed, and a modern light fixture is mounted above.

Home in Claygate

4.84 out of 5 average rating, 19 reviews

Luxury one-bed house centrally located

A beautifully renovated one-bedroom house with its own street entrance, a few steps away from the Parade with its lovely shops and cafes, and from the station with half-hourly trains to Waterloo, taking approx 35 minutes. Convenient access to Hampton Court, Sandown Park racecourse, Kingston-upon-Thames, the A3 and the M25. On-street parking is available nearby.