Holiday rentals in Chessington

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Top-rated holiday rentals in Chessington

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Top guest favourite
The sleeping area features a spacious bed with a patterned coverlet, accented by red and black pillows. A seating area with a dark couch and decorative cushions is visible. A painting adorns the wall above the bed, and light is provided by recessed ceiling lights.
Flat in Sunbury-on-Thames
4.96 out of 5 average rating, 194 reviews

Lovely annexe, short walk to River Thames, Sunbury

A stylish, open plan and friendly space, in Sunbury-on-Thames. 5 minute walk to the River Thames and village. Large, modern, self-contained annexe, behind Sunbury House; own entrance and space for parking. Walking distance to the river, village centre with great pubs and restaurants. Hampton Court, Shepperton Studios and Kempton Park nearby. Easy access to Richmond, Windsor, Heathrow and M3/M25. Overground train to London Waterloo (50 mins). Garage facility to store bikes or canoe / kayak.

Guest favourite
A spacious sleeping area features a four-poster bed dressed in crisp white linens and a colorful mural above the headboard. Light wooden flooring complements the room's modern design. A cozy seating area is included, and natural light enters through multiple windows.
Guest house in Greater London
4.98 out of 5 average rating, 165 reviews

Entire Cabin. Kingston/ Wimbledon/ Waterloo.

Welcome to Applecourt, a lovely self-contained cedar-clad cabin with its own private drive and courtyard. Located just 1 minute away from the A3 on New Malden's Thetford Road, Applecourt is a perfect, relaxing get-away. Enjoy a jaunt down to the Surrey Hills, take in history at nearby Hampton Court palace or catch the train to Wimbledon only two stops away. (Last stop Waterloo!) A true haven away from home, enjoy the cherry blossom courtyard in spring and the juicy pink lady apples in summer!

Top guest favourite
The spacious bed is dressed in white linens, complemented by decorative pillows featuring tropical patterns. Gold sconces flank the bed, illuminating the unique textural wall with intricate patterns. A round mirror adds depth, reflecting the soft lighting in the cozy sleeping area.
Guest house in Surrey
4.96 out of 5 average rating, 295 reviews

Ground floor studio with private entrance

A quiet, ground floor studio flat, fully self-contained, affording high levels of privacy & comfort, with freedom to come & go via your own front door at anytime day or night. Situated in a quiet, safe, leafy cul-de-sac in Cobham (dubbed UK’s Beverly Hills!) which offers: The Ivy, gastro pubs, boutique shops, Waitrose & more. Driving: 5mins to Oxshott station, 10mins to M25, 20mins to Guildford (or train). Airports: Heathrow (10miles), Gatwick (16miles). Trains to London Waterloo: 35mins.

Guest favourite
A modern kitchen area features sleek white cabinetry and a compact countertop. Kitchen appliances, including a microwave and kettle, are visible. Natural light filters through large glass doors that open to a private patio, revealing outdoor seating and greenery.
Guest suite in Esher
4.85 out of 5 average rating, 148 reviews

Cosy 1 bed Guest Suite Esher private entrance

A cosy modern ground floor 1 bed (sofa bed) within our lively family home, with all the basics including own en suite shower room /wc and TV. It is the perfect place for a short stay. There is a small counter to make drinks and small meals including mini fridge freezer and microwave oven. Alternatively if you are preparing a big meal you can use the family kitchen just text me in advance so i can unlock the door and remove our to friendly /energetic dogs. Guest are welcome to use the gas BBQ

Top guest favourite
The detached annex showcases a brick exterior with a pitched roof. A paved pathway leads to the entrance, bordered by potted plants. Lush greenery frames the property, and a gravel area provides additional parking and access to the surrounding garden.
Guest house in Epsom
5 out of 5 average rating, 135 reviews

Peaceful & cosy detached annex with outdoor space

Situated within the grounds of a private property, set back from the road in a leafy residential part of Epsom. Welcome to our peaceful, detached annex offering flexibility, comfort and outdoor space. International guests will find us conveniently situated within 30mins drive of London Gatwick and Heathrow Airports (traffic permitting) and 40mins by train into central London. Ideal for those needing a base to enjoy the delights that Surrey has to offer or somewhere quiet to work from.

Guest favourite
The exterior of the Georgian dwelling is framed by lush greenery, featuring a variety of plants and trees. A well-kept staircase leads to the entrance, showcasing the brick facade and charming windows. Natural light enhances the inviting atmosphere of the surroundings.
Flat in Esher
4.98 out of 5 average rating, 127 reviews

Clive House, Portsmouth Road, Esher, KT10 9LH

Nestled walking distance from Esher High Street the apartment is situated across the courtyard of Clive House, a Georgian dwelling built in the middle of the eighteenth century by Clive of India. The newly refurbished accommodation includes : living area, kitchen/ diner and ensuite double bedroom with a kingsize bed. Living includes a new compact and bijou fully fitted kitchen, dining area with wood burner, luxurious sofa and Smart HD TV/ Sonos sound bar as well as complimentary WiFi.

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, 120 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
A modern living area features a plush gray sectional sofa adorned with colorful pillows. A patterned area rug adds warmth to the space, while a wall mirror reflects light. Adjacent, a compact dining area is seen, with a small table and chairs, leading into an open kitchen.
Guest house in Surrey
4.93 out of 5 average rating, 148 reviews

Private luxury apartment with free Secure parking

Outbuilding with front free parking (only 1 car per booking). Peaceful surroundings with west facing sun (longer days) and wildlife. Close amenities with 24 hour gas station and close shops near by, 7 mins to Epsom town and 6 mins to Chessington world of adventures (by car) and 30 mins trains straight to Waterloo. Very secure apartment as there is CCTV outside in the main house. You will truly enjoy this quiet luxury apartment. *Discount will be offered to returning guests*

Guest favourite
Two friendly donkeys are seen leaning over a wooden fence, wearing red blankets. The stable building, displaying several black stalls, is visible in the background, along with a grassy area that adds to the farm's natural setting.
Farm stay in Surrey
4.82 out of 5 average rating, 262 reviews

Self-contained stable retreat

Set in a traditional equestrian yard, this self-contained purpose-built barn, is set on a farm between the Surrey Hills and Epsom downs. The perfect place to explore and get in touch with nature . The accommodation is a self-contained barn/ stable conversion which you have all to yourselves, accessed from the active stable yard. A lounge, small kitchen, downstairs bedroom upstairs and open plan bedroom leading to the bathroom. Bathroom only accessed via upstairs bedroom.

Top guest favourite
A spacious loft room features a comfortable double bed with soft linens and neatly rolled towels. A cozy seating area includes two chairs and a small dining table. Natural light streams in from a skylight and window adorned with patterned curtains, contributing to a bright atmosphere.
Guest house in Surrey
4.96 out of 5 average rating, 312 reviews

Quaint Self-contained Loft Studio nr Hampton Court

Quaint, quirky, clean and bright for you to relax in private, coming and going as you wish. Nestled in a safe, quiet area, perfectly situated for Hampton Court, Sandown Park Racing, Wimbledon Tennis, Bushy Park with its wild deer, the Thames and great shopping in Kingston. Breakfast included with pubs and restaurants nearby. Within walking distance of two railway stations, direct into London. Twickenham Stadium is just under 30 minutes away. Plenty of free on-street parking.

Guest favourite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Greater London
4.98 out of 5 average rating, 321 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Top guest favourite
An open-plan studio features a king-size bed draped in soft bedding, alongside a cozy day bed adorned with decorative pillows. Natural light fills the space through a skylight, highlighting the warm wooden floor and understated furnishings that promote comfort and functionality.
Guest house in Malden Rushett
4.95 out of 5 average rating, 331 reviews

Cosy detached studio- walking distance to CWOA!

In the village of Malden Rushett, Rushett studio is a self contained studio perfect for all guests. We are a 10 minute walk from the local theme park Chessington World of Adventures so perfect for a weekend away with the kids! We have a local pub The Shy Horse just a 10 minute walk away perfect for a meal with the kids or a quiet drink in front of the log fire. Explore the many walks around us with miles of public footpaths and beautiful scenery.

Popular amenities for Chessington holiday rentals

Quick stats about holiday rentals in Chessington

  • Total rentals

    50 properties

  • Nightly prices starting at

    $39 SGD before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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