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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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, 173 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.

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 Hampton
4.89 out of 5 average rating, 147 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, 313 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.

Top guest favourite
The modern living area features a bright, open space with a cozy seating arrangement and a dining table for four. A large piece of artwork with a coastal theme is displayed on the wall. Warm light fixtures and a green plant add a touch of liveliness.
Flat in Molesey
4.9 out of 5 average rating, 141 reviews

Hampton Court Lodge

Our beautiful, two storey apartment is spacious, modern and light. Only 2 mins walk from the river and its riverside cafes. Featuring large master bedroom with bathroom ensuite, dining for up to 4, kitchen and lounge area with views of the meadow. 8 mins river walk to Hampton Court Station (19 mins to Wimbledon,35 mins Waterloo) and Hampton Court Village on Bridge Road with its fantastic antique shops and eateries on Bridge Road. Hampton Court Palace and Royal Bushy Park are 10-15 mins walk.

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, 176 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, 137 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
4.93 out of 5 average rating, 157 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
4.97 out of 5 average rating, 319 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, 281 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
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
4.91 out of 5 average rating, 122 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
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, 348 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
A clear, geodesic dome reveals a cozy pod interior, surrounded by greenery. An inviting wood-fired hot tub is positioned on a wooden deck, complemented by a dining area. Sunlight illuminates the pod, creating a warm and serene outdoor atmosphere.
Dome in West Horsley
4.94 out of 5 average rating, 377 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Popular amenities for Chessington holiday rentals

When is the best time to visit Chessington?

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Avg. price$128 SGD$132 SGD$130 SGD$149 SGD$150 SGD$161 SGD$155 SGD$155 SGD$146 SGD$147 SGD$142 SGD$149 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.

  • Where should I stay in Chessington?

    Make yourself at home in Chessington by choosing from our most frequently booked neighborhoods. We have over 2,990 vacation rentals in Chessington, over 120 vacation rentals in Malden Rushett, and over 960 vacation rentals in Hook.

  • 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.

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 $38 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!

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