Holiday houses in Chessington

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Quick stats about holiday rentals in Chessington

  • Total holiday rentals

    Explore 60 holiday rentals in Chessington

  • Nightly prices starting at

    Chessington holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,290 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Chessington holiday rentals include Wi-Fi 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
Home in Chessington
5.0 out of 5 average rating, 13 reviews

Architect-Designed Luxury House, 3BR Chessington

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.

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.
Guesthouse in Surrey
4.96 out of 5 average rating, 336 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.

Guest favourite
Cottage in Wisley
4.95 out of 5 average rating, 78 reviews

Luxury Cottage With Ancient Woodland Surrounds

Blackwood is the perfect city retreat sleeping up to four guests amid ancient woodlands. Ideal for families or small groups, it features a spacious open-plan living and dining area that blends cosiness, charm, and comfort. Relax on the large sofa, enjoy the 75" HD TV, high-speed internet, and ample room for board games or puzzles. The Master bedroom boasts a beautiful four-poster bed, while the second bedroom offers a small double. A full kitchen and dining area with private outdoor seating.

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.
Apartment in Esher
4.99 out of 5 average rating, 149 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.
Guesthouse 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, 191 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.
Guesthouse in Surrey
4.96 out of 5 average rating, 333 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
Guesthouse in Surrey
5.0 out of 5 average rating, 301 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
A bright living area features large bay windows that invite natural light. A dark blue couch is complemented by a round dining table surrounded by yellow chairs. A stylish flat-screen television and a wooden console table are present, enhancing the modern design.
Condo in Greater London
5.0 out of 5 average rating, 212 reviews

1 bed annex with en-suite and fully fitted kitchen

In a residential area of Surbiton, with trains to London twice an hour. Berrylands train station is a 15 minute walk away, trains from there to Waterloo in 30 minutes or Wimbledon in 12 minutes where you can pick up the London Underground. See further details in Where we are located under the location map. Own private entrance to ground floor self contained annex flat within our home. Fully fitted kitchen with washing machine, tumble dryer, wine chiller.

Guest favourite
Condo in Surrey
5.0 out of 5 average rating, 6 reviews

Modern Studio near London | EV Charger

Comfort, style, and convenience await in this fully modernised studio. Perfectly located for Wimbledon, Clapham, Kingston University, Epsom Hospital, and Chessington World of Adventures. Features a cosy bed, well-equipped kitchenette, dining area, sleek bathroom, and private parking. Ideal for couples, solo travellers, or business stays seeking a quiet, well-connected base near London. An EV charger is available; additional charges apply and paid directly.

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, 368 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.

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.
Guesthouse in Chessington
4.95 out of 5 average rating, 388 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

When is the best time to visit Chessington?

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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 20 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 30 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 30 house rentals with free parking in Chessington. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.