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House holiday rentals in Chessington

Find and book unique houses on Airbnb

Top-rated house rentals in Chessington

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

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Superhost
A living area features a dark sofa arranged with patterned cushions. An art piece depicting the sea hangs on the wall. A coffee table is centered on polished wooden flooring, complementing the light-colored walls and large windows dressed with shutters that allow natural light to fill the space.
Home in Surrey
4.96 out of 5 average rating, 70 reviews

High Street Apartment ESHER

Newly converted town centre apartment in fantastic order throughout, offers bright, generous-sized living space. One generous sized double bedroom, ultra modern shower room, fully fitted open plan kitchen (including dishwasher) /reception room. Unlimited high speed internet connectivity. Free, designated parking is available in 100 m. Esher High Street has an excellent range of restaurants including Waitrose, Cote, Giggling Squid, The Good Earth an Everyman Cinema along with coffee shops, pubs.

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, 130 reviews

Film Studio*Heathrow Airport*Families*Long Stays

Outstanding Property with Excellent Reviews (4.95/5 from 156 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

Top 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 Sutton
4.93 out of 5 average rating, 119 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. All house trained dogs of all sizes welcome. EV charging points are NOT on premise. They are on street charging points.

Superhost
The exterior of a charming Edwardian house features a brick facade with white window frames and decorative details. Flower boxes are aligned beneath the front windows, and a blue door adds a welcoming touch. The driveway provides off-street parking, bordered by neat greenery.
Home in Surrey
4.81 out of 5 average rating, 74 reviews

Epsom/London, parking, shops and train to town.

A large period Edwardian house with high ceilings, decorative coving, chandelier lighting and fireplaces. The house is a ten minute walk to the town centre of Epsom where you will find shops and restaurants including Waitrose, Gails, Costa, Oliver Bonas, Caballo Lounge, The Picture House, an arthouse cinema and a leisure centre. Epsom has a train station from where you can travel to London Waterloo in 35 minutes. Epsom has numerous bus routes which end in Croydon, Sutton, Morden and Kingston.

Top guest favourite
The image captures an aerial view of a charming Tudor property surrounded by lush greenery. Two distinctive white-tipped oast houses are prominently displayed, along with neatly manicured gardens and open spaces. The serene countryside landscape extends into the background, showcasing rolling hills.
Home in Brasted
4.96 out of 5 average rating, 329 reviews

Oast Farmhouse, Ide Hill, Hever, Edenbridge

The Oast House is on a private Tudor Estate. A listed mid-Victorian property has charming period features, a large garden and storage. It theoretically sleeps 10 but suitable for 7 if one prefers sleeping alone. Terrific for group bookings, cycling and triathlon participants, temp workers, golfers, extended families in area for special occasions, corporate charity rides, or bake off weekends! Perfect for visiting Tudor England all around beautiful West Kent. We are 35 mins from South London

Top guest favourite
Home in Surrey
5 out of 5 average rating, 9 reviews

Tudor House

Tudor House is a newly refurbished 2 bedroom house, situated 1 minute walking distance to the world famous Epsom Downs Racecourse, home of the Epsom Derby. This delightful property has a spacious living room area, 1 downstairs WC, stylish kitchen and patio area. Upstairs you will find a comfortable double bed, wardrobes, TV and dressing table. The second bedroom consists of 2 single beds which can be made into a double, fitted wardrobe and TV. The upstairs bathroom has a bath and shower.

Top guest favourite
A light-filled living area is furnished with a plush sofa and decorative pillows. A stylish coffee table sits centrally on a patterned rug. Lush plants add a touch of greenery, while a large television rests against a sleek media console, enhancing the inviting ambiance.
Home in Surrey
4.93 out of 5 average rating, 159 reviews

Virginia Water Family Getaway

Lambly Hill House – Holiday Rental in Virginia Water, Surrey Welcome to Lambly Hill House, a stylish and spacious 4-bedroom holiday rental in Virginia Water, Surrey. Perfect for families, golf visitors and business travellers, this beautifully renovated home offers modern comfort, peaceful surroundings and a private garden in one of Surrey’s most desirable locations. Located just a short walk from Virginia Water train station, Lambly Hill House provides easy connections to central London.

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 Surrey
4.99 out of 5 average rating, 215 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
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, 131 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
A spacious living area features a large, comfortable corner sofa, complemented by accent pillows and a sleek coffee table. Expansive windows provide scenic views of the outdoors, while a modern fireplace adds warmth. The dining area is visible in the background, showcasing elegant seating.
Home in Surrey
5 out of 5 average rating, 6 reviews

Twilight Retro Haven + Hot Tub + Garden Cinema

Step into Kooringa, an Asian-inspired retro haven in Warlingham, Surrey. This stylish retreat offers a luxurious hot tub, a garden cinema for magical movie nights, and stunning countryside views. Just 10 minutes from Upper Warlingham Station (direct to London in 30 mins), it's perfect for couples or small groups. Explore local gems like Surrey Hills, enjoy the secluded garden, and unwind in retro-modern comfort. Your idyllic escape, just a short journey from city life, awaits!

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.

Top guest favourite
Home in Surrey
5 out of 5 average rating, 9 reviews

Executive 2 En-Suite BR W/ Parking, Self Check-in

Kick back and relax in this calm, stylish space. Close toTrain Link to London! The space Modern townhouse with 2 en-suite bedrooms in West Ewell, near Epsom Sleeps 4, making it ideal for tourists, families, friends, business travellers or contractors. With easy access to central London and a range of local attractions, this home offers the perfect blend of city convenience and peaceful retreat

Popular amenities for house rentals in Chessington

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 $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 300 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 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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