Holiday rentals in Chessington

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Top-rated holiday rentals in Chessington

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern living area is highlighted by a spacious sectional sofa with a soft throw, complemented by a glass table and white chairs in the dining nook. A large mirror reflects light from the window, while a wall-mounted television provides entertainment options.
Flat in Surrey
5 out of 5 average rating, 66 reviews

Modern flat in central location

Enjoy unparalleled comfort in our top-floor 2BR flat in central Epsom, just 5 min from the station & high street. Sleep soundly in a king, double, or single bed, and relax in a stylish space featuring a 55" Smart TV, espresso machine, and more. Benefit from secure parking, a peaceful setting, and proximity to town. Modern aesthetics meet practicality in our recently refurbished, secure building. Ideal for exploring Surrey or soaking in the quiet. Your serene, chic getaway in the heart of it all!

Top guest favourite
The room features a spacious double Queen bed adorned with clean white linens. A bedside table with a lamp complements the bed. A small TV is positioned on a stand across from the bed, while natural light enters through a nearby window.
Guest suite in Claygate
4.94 out of 5 average rating, 175 reviews

Studio, own access, self contained.

The room has it's own entrance door. It has a double Queen size bed, shower room and kitchen area (tea, coffee, cereal etc supplied) with fridge, microwave and single induction hob. There is a sofa, TV & table with two chairs. Our home is about a 15 minute walk to Claygate station. Trains direct to London Waterloo (35 mins) and Guildford. Claygate has local shops and a CoOp, several pubs and restaurants and we are close to a bus stop with a frequent bus service to Kingston for major shops.

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, 137 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, 131 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.

Guest favourite
A stylish cabin interior showcases a warm wood structure, featuring a cozy sleeping area with a neatly made bed. A round dining table is paired with two chairs, illuminated by soft lighting. An outdoor seating area is visible through the window, surrounded by wooden fencing.
Cabin in Royal Borough of Kingston upon Thames
4.91 out of 5 average rating, 101 reviews

London & Surrey Cub House

Your own private stylish cabin, own entrance, self check-in. King-size bed, en-suite, kitchenette & private outside space. 8min walk to 2 stations into central London (Waterloo 25min, Wimbledon 15min). Good links to Hampton Court, Kingston upon Thames, Surrey walks and villages. Superloop 7 Bus (SL7) direct to and from Heathrow Airport, 1hour. Very quiet residential road with free parking. No more than 2 guest permitted at anytime on the property. No smoking/vaping on the property.

Top guest favourite
Rowers glide across the still waters beneath an arched bridge adorned with decorative lamps. Moored boats with wooden tables are positioned in the foreground, reflecting the vibrant autumn foliage from trees lining the riverbank.
Flat in Royal Borough of Kingston upon Thames
5 out of 5 average rating, 11 reviews

Sunny Riverside Victorian Flat

Charming Victorian conversion set on idyllic River road Location: Picturesque, tree-lined street just 2 minutes from the Thames and 20 mins to Central London. Bright, sun-filled rooms, thoughtfully decorated with warmth—this is my home, not just a rental. Fully equipped kitchen and spacious bedroom. Enjoy scenic walks or bike rides to nearby attractions – Hampton Court Palace, Richmond Park, and Kingston’s lively market . Quiet street with cafés, shops, and all essentials nearby.

Top guest favourite
The exterior of the studio features a smooth patio area framed by potted plants and a wooden bench. Large windows line the front, allowing natural light to enter. The presence of greenery enhances the serene ambiance, set against a clear blue sky.
Guest house in Ewell
4.98 out of 5 average rating, 52 reviews

Studio in Epsom

This quiet studio is a 15 minute walk from Ewell West train station for a 35 minute direct train to Waterloo. The studio has; - fully functioning kitchen (combination microwave, induction hob & a milk frother (a necessity in my world)) with dining table, - relaxing space to watch TV - dedicated work space with great internet access, - cosy yet firm double bed, all feathered pillows and duvet - skylit shower bathroom, - free parking, - washing machine available (on request)

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, 149 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*

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, 313 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.

Top guest favourite
A bright lounge area features a comfortable sofa with plaid cushions, alongside a dining table and chairs. Large skylights and glass doors illuminate the space, opening to a patio garden filled with greenery. Two framed artworks enhance the inviting ambiance.
Guest house in Surrey
5 out of 5 average rating, 266 reviews

Self Contained Cottage in Thames Ditton Village

Beautiful self contained 1 bedroom cottage in the grounds of one of Thames Ditton’s oldest properties. Superbly located next to the river with pubs, restaurants, coffee shops, and village stores close by. Thames Ditton is a pretty village located close to Hampton Court, Surbiton, and Kingston Upon Thames and 30 minutes by train to London Waterloo. Go Boat hire is a minutes walk and the slipway to the Thames is opposite the house if you have your own paddle board/canoe.

Top guest favourite
Home in Surrey
5 out of 5 average rating, 74 reviews

Beautiful two bed lodge with free parking in Epsom

This peaceful self contained house, offers easy access to town and countryside. Epsom racecourse is a 15min walk away. Accessible from Gatwick (28 mins) and Heathrow (35 mins), Epsom train station is a 15 min walk away with trains to Waterloo, London Bridge and Victoria. Plenty of shops and restaurants in the town centre and the charming Grumpy Mole at the Amato is a 2 min walk. Chessington World of Adventures is 15 mins by car. Free off road parking for one car.

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 Royal Borough of Kingston upon Thames
4.98 out of 5 average rating, 328 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.

Popular amenities for Chessington holiday rentals

When is the best time to visit Chessington?

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Avg. price$132 SGD$136 SGD$133 SGD$153 SGD$154 SGD$166 SGD$159 SGD$159 SGD$150 SGD$162 SGD$133 SGD$147 SGD
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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Chessington?

    Experience the best of Chessington with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chessington have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Chessington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chessington?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Chessington?

    Yes! Work meets play with ease at over 10 vacation rentals in Chessington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Chessington have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Chessington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chessington?

    Chessington has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Where should I stay in Chessington?

    Make yourself at home in Chessington by choosing from our most frequently booked neighborhoods. We have over 2,970 vacation rentals in Chessington, over 110 vacation rentals in Malden Rushett, and over 1,000 vacation rentals in Hook.

  • Are there pet-friendly vacation rentals in Chessington?

    Four-legged friends are welcome in Chessington. Choose from more than 10 vacation rentals for guests traveling with pets.

Quick stats about holiday rentals in Chessington

  • Total holiday rentals

    Explore 50 holiday rentals in Chessington

  • Nightly prices starting at

    Chessington holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 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!

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