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 $50 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.

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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
4.93 out of 5 average rating, 136 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.

Top Guest favourite
A two-story white house with a gabled roof is positioned in a residential area. The main entrance features a welcoming porch framed by potted plants. A paved driveway leads to the door, with neighboring houses and greenery visible on either side.
Home in Addlestone
4.95 out of 5 average rating, 147 reviews

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

Guest favourite
Home in Chessington
5.0 out of 5 average rating, 14 reviews

Unique Architect-Designed 3BR Home, London

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). Minutes walk to Chessington World of Adventure, golf courses and more.

Guest favourite
Home in Chessington
4.87 out of 5 average rating, 31 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
Home in Surrey
4.88 out of 5 average rating, 48 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.

Superhost
Home in Surrey
4.81 out of 5 average rating, 86 reviews

Surrey/London. Home for 6/8 people. Fibre WiFi.

A lovely Edwardian period house 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.

Top Guest favourite
Home in Hampton
4.92 out of 5 average rating, 26 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 East Molesey
5.0 out of 5 average rating, 140 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, 137 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.

Guest favourite
The bedroom features a spacious bed with neutral-toned linens, complemented by decorative pillows. A dresser and bedside tables flank the bed, and large windows allow natural light to fill the room. A stylish canvas art piece decorates the wall above the bed.
Home in Surrey
4.78 out of 5 average rating, 41 reviews

Spacious Family Bungalow with Garden for up to 7

Spacious & Family friendly 2 bedroom bungalow with large garden. Lots of natural light. Open plan lounge with double sofa bed, 55" large TV & fully fitted kitchen with appliances and essentials. Finished to a very high and stylish standard. Comfortable bedrooms (king, double, single size beds and double sofa bed) & fully fitted guest bathrooms with WC and a separate toilet. Close to the town centre and train station with direct high-speed links to London.

Superhost
A modern kitchen is illuminated by natural light from skylights, featuring sleek cabinetry and stainless steel appliances. A dining set for four is positioned near windows, with light wood flooring enhancing the spacious feel. Neutral-colored curtains frame the windows.
Home in Greater London
4.91 out of 5 average rating, 79 reviews

3 bedroom house with parking

Situated in Tolworth with private parking and just only 10 minutes walk from Tolworth Station and 12 minutes walk to local shops. You can take local train to Wimbledon just 4 stops (15 minutes) or 25 minutes and end up in London Waterloo. On another hand you only 6 km from from Kingston Upon Thames. Travel from Gatwick is very easy just take a train to Clapham Junction and then train to Tolworth Station. London Heathrow is accessible tube and train.

Top Guest favourite
A historic suspension bridge spans across calm waters, lined by boats of various sizes. Trees and buildings can be seen in the background under a soft, twilight sky. The reflection of the bridge and surroundings creates a peaceful scene on the water's surface.
Home in Surrey
5.0 out of 5 average rating, 35 reviews

Welcome to The Cottage - Thames Ditton, Surrey

Relax with the family. A quaint 2 bedroom cottage in the heart of the historical village of Thames Ditton. With off street parking and a beautiful garden, you can enjoy a coffee on the patio or simply walk a minute to a selection of cafes, restaurants and village stores. A perfect place to start and end your day, whether it be sightseeing in London, going to the races, visiting Hampton Court Palace or nearby National Trust properties.

Popular amenities for Chessington house rentals