Holiday houses 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 charming outdoor area is surrounded by trees, featuring a wooden cabin and a circular seating arrangement. Two wooden lounge chairs are positioned near a fire pit, with a winding pathway leading toward the cabin, creating a serene and inviting atmosphere.
Shepherd’s hut in Headley
5 out of 5 average rating, 388 reviews

Luxury Woodland Shepherds Hut & Romantic Hot Tub

Escape to your own little bit of luxury in the stunning Surrey Hills, conveniently about an hour from London, and stay in one of our two gorgeous shepherd's huts. We are located near the village of Headley near Box Hill, so you can enjoy beautiful countryside walks, whilst staying in a luxury hut with modern facilities like high speed wifi! Dog friendly (extra fee). We have a wood fired couples hot tub and can supply grazing platters, perfect for birthdays, anniversaries and special nights away!

Top Guest favourite
An outdoor hot tub is situated on a wooden deck, surrounded by lush greenery. A seating area with a light-colored chair offers a comfortable spot to relax. Large sliding glass doors lead into the retreat, allowing for seamless indoor-outdoor access.
Shepherd’s hut in Royal Kingston upon Thames
4.99 out of 5 average rating, 170 reviews

Lavish Retreat & Champagne 30mins Taxi from London

The Little Touch of Grey, provides an electric ambiance and the perfect setting for the elite of mind, who wants to reward both themselves and their partner. We are proud to share the latest addition to our portfolio with those who appreciate of all things bespoke. Included are; a complimentary bottle of Champagne, indoor & outdoor Jacuzzi, underfloor heating, sound system and salacious yet tasteful surprises throughout. For special occasions, use our secret compartment to add to your surprise.

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, 305 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 living area features high wooden beams and a large window allowing natural light. A comfortable sofa is placed alongside classic armchairs. A kitchen area with cabinetry is visible, complemented by a decorative lamp and houseplants. Soft textures enhance the cozy environment.
Cottage in Chobham
4.99 out of 5 average rating, 110 reviews

Beautiful oak barn in peaceful countryside setting

Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

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.
Apartment in Esher
4.99 out of 5 average rating, 134 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 Kingston upon Thames
4.91 out of 5 average rating, 108 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
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
4.93 out of 5 average rating, 154 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.
Guesthouse in Surrey
4.97 out of 5 average rating, 315 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.
Guesthouse in Surrey
5 out of 5 average rating, 273 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
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 Malden Rushett
4.95 out of 5 average rating, 354 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.

Top Guest favourite
The exterior of Grace Cottage features large glass doors framed by a decorative curtain. A glimpse of the interior reveals a cozy living area adorned with a patterned rug and a grey sofa. The structure is complemented by blooming trees and a stone pathway.
Guest suite in Surrey
4.95 out of 5 average rating, 141 reviews

Grace Cottage

Grace Cottage is an annex on the side of our home. Access is via a locked side gate and then you will need to cross the main house patio area to get to the separate entrance to the flat. It is set up with the bedroom and living area being in one space, with a mezzanine floor where a single mattress is situated. There is a fully kitted kitchen with hob, oven, fridge/freezer, microwave, sink and dishwasher. Shower room with basin, toilet and shower.

Popular amenities for Chessington holiday rentals

When is the best time to visit Chessington?

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Avg. price$176 NZD$181 NZD$178 NZD$204 NZD$206 NZD$221 NZD$213 NZD$213 NZD$200 NZD$216 NZD$178 NZD$197 NZD
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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 apartment rentals in Chessington have wifi?

    Absolutely! We offer over 10 apartment 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 990 vacation rentals in Hook, over 120 vacation rentals in Malden Rushett, and over 2,970 vacation rentals in Chessington.

  • 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 $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 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

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chessington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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