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House holiday rentals in Chessington

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Top-rated house rentals in Chessington

Guests agree: These houses are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of the property is displayed, featuring a blend of traditional and modern architecture. A courtyard with landscaped greenery is visible at the center, surrounded by the building's stone facade. Tall trees and blue skies add a serene backdrop to the scene.
Home in Englefield Green
4.87 out of 5 average rating, 173 reviews

Charming 5* Hse Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, a beautiful bathroom, abundant art and character; the property looks onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Top Guest favourite
A two-story white house with a gabled roof is positioned in a residential area. The main entrance features a welcoming porch framed by potted plants. A paved driveway leads to the door, with neighboring houses and greenery visible on either side.
Home in Addlestone
4.95 out of 5 average rating, 122 reviews

Legoland * HeathrowAirport * Families * Long Stays

Outstanding Property with Excellent Reviews (4.95/5 from 150 Guests) Nestled in a picturesque area, this property offers a perfect balance of tranquillity & convenience. Enjoy a short stroll to the scenic canal, lush farmlands, and numerous attractive footpaths. Key amenities are just moments away, including Addlestone train station, GP services, a pharmacy, Tesco Extra, shops, and cozy cafés. Weybridge is also within walking distance. Discover the perfect stay at our highly-rated property

Guest favourite
A studio space features a spacious bed covered with a grey duvet and towels neatly arranged on top. A small dining area with a chair is visible, along with a kitchenette equipped with modern appliances, including a washing machine and black tile backsplash.
Home in Greater London
4.91 out of 5 average rating, 114 reviews

Luxurious studio in Sutton, with parking space

This little gem is the perfect stay for singles and couples. The accommodation is a 4 minutes drive to Sutton station or a 10 minute bus journey. We have many buses stationed near the studio travelling to Morden, Wimbledon, Tooting and other various locations across South west London. Great restaurants, shops and amenities are available on Sutton High street with only a 5 minute walk. The studio is also located 35 minutes from Victoria station and London Bridge, Central London. Parking available

Superhost
Home in Royal Borough of Kingston upon Thames
5 out of 5 average rating, 10 reviews

Beautiful 4BR Oasis, Chessington Gem, Free Parking

Welcome to this newly renovated, stylish retreat in Chessington, London. This spacious 4-bedroom home blends comfort with elegant interiors, perfect for families or groups. Enjoy a fully equipped kitchen, cosy living area, a private garden to relax in and great transport links to London. Driveway parking space for 2 cars. Located close to Chessington World of Adventures. Whether you’re here for work or leisure, this inviting gem of a home has everything you need for a memorable stay.

Guest favourite
The outdoor seating area features a rectangular table with a decorative flower arrangement, arranged on a light-colored tiled surface. In the background, large glass doors open to a stylish interior, revealing a modern kitchen and comfortable sofa.
Home in Greater London
4.92 out of 5 average rating, 105 reviews

The Nook

Kick back and relax in this calm, stylish space. This ground floor one bed apartment is perfect for romantic getaway with your partner, or if you are in town for work and you are looking for a home away from home. If you have a little one you want to bring with you. Victoria station is a 20 minute train away, as well as being 15 minutes away from Wimbledon and Croydon by tram. Small to medium dogs are also welcome. EV charging points are NOT on premise. They are on street charging points.

Top Guest favourite
The exterior view of the property showcases a black wooden structure with prominent gabled roofs and dormer windows. A warm, inviting entryway is framed by greenery, and a wooden gate is visible, providing access to a secluded area.
Home in Burpham
4.99 out of 5 average rating, 204 reviews

Ty Bach

A cosy, clean, warm and light annexe with its own walled garden. Situated on a beautiful private road a short walk from the historic cobbled streets of Guildford town centre with its numerous boutique shops and quality independent restaurants. Ty Bach is on the edge of the beautiful Surrey Hills (a designated Area of Outstanding Natural Beauty) and the Rivey Wey. It is the perfect destination for walkers, mountain bikers and lovers of the outdoors. Dog walking and country pub heaven!

Top Guest favourite
A modern summerhouse is depicted with bifolding glass doors open to the garden. Inside, a well-equipped kitchen is visible along with a sitting area featuring a Smart TV. The space is brightly lit, with neutral-colored walls and a streamlined design.
Home in Greater London
4.96 out of 5 average rating, 114 reviews

Garden Summerhouse w/ Parking

Private garden summerhouse with full bathroom and kitchen at the back of our garden. The summerhouse is newly built, has full bifolding glass doors and it includes a Smart TV with Utra Fast WIFI. Our house is 5-minute walk from the heart of Wimbledon City Centre and Wimbledon train, tube, and tram station. There is a wide variety of restaurants, shops and supermarkets in the area. The property is tucked away in a quite road and has a modern garden with a beautiful mature cherry tree.

Guest favourite
The living area is characterized by a light wood floor and minimalist decor. A dining table for two is seen beside a wooden television console. A comfortable sofa bed is positioned along one wall. Greenery enhances the space, with a decorative wall mirror reflecting natural light.
Home in Fetcham
4.99 out of 5 average rating, 71 reviews

A Cozy Home Away from Home

Welcome to our charming one-bedroom house in the picturesque village of Fetcham, Surrey. Perfect for a romantic getaway or a solo retreat, this cozy home offers a tranquil setting with all the amenities you will need. Step inside to find a well-appointed living space with a fully equipped kitchen, and a dining area for two. The bedroom features a plush kingsize bed with soft linens, ensuring a restful night's sleep. A shower only Bathroom, stocked with essentials for your convenience

Top Guest favourite
The open plan living area features gabled ceilings and stylish furnishings. A comfortable sofa sits across from a galley kitchen with modern cabinetry. French windows open to a private patio garden, while natural light enters through sheer curtains, creating a bright and inviting atmosphere.
Home in Molesey
5 out of 5 average rating, 124 reviews

Hampton Court: Spacious, Bright & Tranquil Annexe

Our newly renovated spacious 2 bedroom annex is situated in a wide tree lined road, a premier location just a few minutes walk away from the charming cafés, shops and restaurants of Hampton Court Village, Hampton Court Palace and local train station. Adjacent to but detached from our elegant Victorian family home, this bright and stylish space is tranquil and self contained and enjoys additional benefits of a private south facing patio garden and dedicated off street parking space.

Superhost
The image showcases a cozy living area featuring a comfortable sofa with yellow cushions, a colorful area rug, and a round coffee table. Natural light enters through window blinds, illuminating the space. A modern bathroom with a glass shower is visible in the top left corner.
Home in Surrey
4.9 out of 5 average rating, 162 reviews

Free Parking 25 Min central London close to statio

JUST 25 Minutes by train to central London and just over an hour to the Cotswolds. FREE cancellation up to 24hrs prior to arrival. No damage deposit required, no cleaning fee or hidden charges. Outside of Londons ULEZ zone. FREE Parking. sleeping up to 5 this cosy house is a luxury renovated 1 bed in a quiet gated development. King size, double & single sofa beds. Close to Brooklands, Windsor, Ascot Thorpe Park, Legoland,Chessington , Wisley, Hampton Court, Heathrow

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
4.92 out of 5 average rating, 112 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.

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.

Popular amenities for Chessington house rentals

Quick stats about house rentals in Chessington

  • Total holiday rentals

    Explore 20 holiday rentals in Chessington

  • Nightly prices starting at

    Chessington holiday rentals start at $71 NZD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    20 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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