
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.

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.
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.

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.

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.

Beautiful 3 Bedroom Cottage In Central Dorking
Welcome to our fantastic newly renovated 3 bedroom home located in Dorking. Beautifully presented throughout, this self catering home benefits from an open plan fully equipped kitchen / lounge / diner with patio doors leading out to the courtyard which has its own outdoor dining area, which is well lit and full of gorgeous foliage. Spread over 4 floors there are 3 bedrooms that can comfortably accommodate up to 5 guests and two stunning bathrooms, both equipped with shower, sink and toilet.

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.

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!

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.

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.

Private annexe in Old Windsor.
A private double bedroom annexe, with its own entrance, separated from main house. Private bathroom and full use of the gymnasium and lovely garden. (which includes a small wood area). The house is situated right on the doorstep of Windsor Great Park, in Old Windsor. Windsor town centre is 3 miles away and we are close to Heathrow and the M25 and M4.

House near Epsom, ideal for business travelers
Ideal for business travelers, a 3 bed house in Ewell West. #Adults only #. Close to Epsom, Sutton, Kingston & Wimbledon. London 30 mins by train. Heathrow and Gatwick airports 30-40 mins. Epsom Racecourse 15 mins. Golf, Walking, Farms and other leisure activities nearby. * School zone no entry between 8-9am, 2.30-4pm*

Stylish Home in the Heart of Cobham - Free Parking
Set on a quiet and desirable road off Cobham high street , this gorgeously newly renovated 4-bedroom home offers a bright, modern and stylish base just outside London. With free off-street parking, a private garden and flexible sleeping arrangements, it’s ideal for families, small groups or longer stays.
Popular amenities for house rentals in Chessington
House rentals with a pool

Blackham Farm

Bright spacious home with natural swimming pond

Kensington Pool & Piano | Unique 3BR w/ AC, Garden

Wellness Escape by River: Sauna, Pool, Hot Tub

Old Wharf Cottage

Serene and private double ensuite overlooking pond

Surrey Cottage with indoor heated swimming pool

Woodland Escape with Heated Pool
Weekly house rentals

Luxury house with annex

Welcome to The Cottage - Thames Ditton, Surrey

3 bedroom house with parking

Little Burley

Beautiful 1870s Victorian House on River Thames

A luxurious country retreat with Jacuzzi hot tub

The Lodge

Cozy 3 Bedroom Terrace Cottage in Epsom
Private house rentals

The Royal Paddock

Detached 6 bedroom family house with Sky TV

Charming Walton Home with Sunny Garden

Calm spacious home w/ large terrace & free parking

A Cozy Home Away from Home

Peaceful home, Surbiton -FreeParkings-No Guest Fee

The Stanley Modern 3/4BED 3BATH | Comfort & Style

Family home near Hampton Court (Sleeps 8)
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 £23 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!
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- ExCeL London
- The O2
- Brighton Seafront
- Tower Bridge
- Emirates Stadium
- West Wittering Beach
- Clapham Common
- University of Oxford
- Goodwood Motor Circuit
- South Downs National Park
- Buckingham Palace
- Thorpe Park Resort
- Alexandra Palace
- Chessington World of Adventures Resort
- Big Ben
- London Stadium
- Windsor Castle





