Holiday rentals in Chessington

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Quick stats about holiday rentals in Chessington

  • Total holiday rentals

    Explore 40 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 1,330 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

    40 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!

Top-rated holiday rentals in Chessington

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

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Guest favourite
A modern living area features a light-colored sectional sofa adorned with decorative pillows. A plush area rug complements the space, while a dining table with grey chairs is visible in the background. Bright, ambient lighting enhances the open layout, with a kitchen area showcased subtly beyond.
Flat in Surrey
4.95 out of 5 average rating, 179 reviews

Elegant Epsom Flat in Period Building

Our spaces are designed solely for the use of our guests, not someone elses home rented while they are away for a while. Neither do we think of them as serviced apartments, we try to create spaces where you will feel at home from the moment you walk through the door. We do not cut corners and consistently invest in our properties to create an environment we would want to live in ourselves. We do charge a bit more but everything you need to run the apartment is in the price, whether its the bathroom toileteries, the dishwasher tablets and whatever you need for all the appliances and even the bathrobes and the hairdryers. We stock the fridge with the basics as we know the last thing you want to do after a long trip is to have to make that trip to the supermarket to buy that pint of milk. We like to welcome our guests personally on arrival, but if you wish checkin can be as easy as punching in the code into the lockbox outside the front door, And at departure, simply leave the keys on the table and close the door behind you. No more anxious waiting at reception as someone departs to your room to audit what you said you had from the minibar. Our goal is to make travelling easier combining the comfort of a home from home with the attention to detail of a hotel. We are very grateful to the guests who have given us such kind feedback and we hope to welcome you to stay with us in Epsom in the future. Well essentially, its your home for the duration you are with us. You have the keys. You have access to the whole flat. Noone is going to show up unexpected. We have secure parking outside. We can provide additional services such as cleaning and bedding and linen change at a small extra charge on request and with advance notice we can provide surprise special touches for you on arrival for those important or romantic occasions. We are available at short notice to help with any issues which guests may face - though we will leave you to your own devices. For stays of 7 days or more we offer are least one cleaning and bedding change a week. The apartment is situated right in the town centre, so everything is available right outside the door. Major restaurants and shops are within a five-minute walk, and it's close to the station. The location could not be better or more convenient. We have secure private parking and can accomodate 1 car per apartment. There are other parking options nearby most notably the Ashley centre which is a 5 minute walk. The station is about 300 metres away. Uber is pretty good and usually arrive in less than 10 minutes. The best local taxi firm in our view is Clocktower Cars which is in our House Manual.

Top guest favourite
A bright and airy living space is illuminated by natural light, showcasing large windows that provide views of the river and surrounding greenery. Light wooden flooring complements the white walls and modern furnishings, including a dining table and chairs positioned near the window.
Apartment in Richmond upon Thames
4.9 out of 5 average rating, 158 reviews

Flat overlooking the river at Hampton Court

A unique self-contained flat with panoramic views over the Thames at Hampton Court, suitable for a couple or single and available for longer lets of up to one month. Situated on the upper deck of a modern floating home, with all mod cons as standard, the flat has a spacious living room / kitchen, together with compact bedroom and en-suite bathroom, and is accessed via its own stair-case. The island where the houseboat is moored is easily accessible via its own road bridge, with safe parking.

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, 331 reviews

Ground floor studio flat

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.

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
4.95 out of 5 average rating, 66 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; - air conditioning - 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 freestanding bathtub filled with water and flower petals is complemented by a wooden tray holding a glass of wine and an open book. A large ornate mirror and wall-mounted lights enhance the serene atmosphere. A hand towel and bath robe hang nearby.
Place to stay in Box Hill
4.97 out of 5 average rating, 178 reviews

Potting Shed, freestanding bath

Welcome to The Potting Shed Surrey Hills it’s ian exquisite retreat, offering a perfect blend of luxury and tranquility. Watching the sunrise while soaking in your freestanding bath amidst 6 acres of private land is truly magical. It’s luxurious and stylish decor creates an unforgettable experience for guests seeking relaxation and indulgence. From AONB country walks to the personalised room service, the Potting Shed offers a level of extravagance that sets it apart from other retreats.

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, 178 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 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
4.99 out of 5 average rating, 146 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 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
4.92 out of 5 average rating, 159 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 charming brick exterior of the apartment is surrounded by lush greenery, with a well-maintained pathway leading to the entrance. Soft outdoor lighting highlights the features of the building, creating an inviting approach shaded by trees and shrubs.
Guest suite in Long Ditton
4.97 out of 5 average rating, 188 reviews

Self Contained with private entrance, Surbiton

The Courtyard is a luxury, completely self contained apartment, safe and secure with its own private entrance. The king size bedroom and seating area overlook our courtyard in leafy Long Ditton. Close to Surbiton with trains direct to London Waterloo in just 16 minutes. Access to the suite is from a key safe. Guests can enjoy complete privacy during their stay, while we live in separate on-site accommodation should you have questions. Parties and gatherings are not permitted.

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, 329 reviews

Quaint Self-contained Loft Studio nr Hampton Court

Quaint, homely, 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
Guest house in Surrey
5 out of 5 average rating, 294 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.

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 Chessington
4.98 out of 5 average rating, 361 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$174 SGD$154 SGD$151 SGD$151 SGD$152 SGD$164 SGD$158 SGD$158 SGD$149 SGD$150 SGD$145 SGD$151 SGD
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Frequently Asked Questions

  • 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.

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

    Experience the best of Chessington with our house 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.

  • 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.

  • 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 a kitchen?

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

  • 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.

  • 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.

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