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
A spacious living area features a comfortable sectional sofa adorned with colorful throw pillows. A light rug defines the seating space, while natural light filters through large windows. Minimalist decor elements, including a mounted antler and lanterns, add character to the neutral-toned walls.
Home in Englefield Green
4.97 out of 5 average rating, 130 reviews

Five Star Boutique House 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, beautiful bathrooms, abundant art and character; the properties look 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, 125 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, 118 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
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, 68 reviews

Epsom, parking, near food/shops, train to London.

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.

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
4.93 out of 5 average rating, 109 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, 207 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 cozy lounge area is featured with a corner sofa and a television. Storage units with a mix of open and closed compartments are positioned alongside a window that brings in natural light. A dining table is visible in the background, against a gently sloped wall.
Home in Greater London
4.96 out of 5 average rating, 110 reviews

Beautiful 2 bedroomed home in Wallington

This is a beautiful, stylish, recently refurbished two bedroomed self contained annexe in a quiet residential, tree lined road. Fully fitted kitchen with oven, hob, fridge, freezer, microwave, washing machine & dishwasher. Lounge/dining area with corner sofa, sky tv and dining table. Upstairs - bedroom with a double bed, wardrobe, tv & chest of drawers, bedroom 2 with single bed & wardrobe. The bathroom has a bath with overhead shower. Parking available. Wi-fi throughout. No smoking

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.

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, 126 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.

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, 115 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, 75 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.

Top Guest favourite
The image shows the entrance of a brick cottage, featuring a wooden door and a small step leading to it. A picket fence borders the grassy front yard, which is well-maintained. A planter with flowers is visible near the door, complementing the home's inviting exterior.
Home in Molesey
4.98 out of 5 average rating, 128 reviews

Lovely bright 2 bed home close to Hampton Court

We are situated just half a mile from Hampton Court where you will find an array of restaurants, cafes and shops to peruse and just a three minute walk from a large open park leading down to the River Thames. However, please note - Hampton Court is not in London and if you want to be close to London we may be too far for you. There is railway station which is about a 10 - 15 minute walk away and the line takes you to London Waterloo (a 35 minute journey).

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 $69 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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