
House holiday rentals in Chessington
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Top-rated house rentals in Chessington
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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.

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

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.

The White House Oxshott
Bring the whole family and friends to this great place with lots of room for fun. The house sits on 0.5 acre plot of land, with ample gardens and 4 cars parking driveway. Recently renovated benefiting AGA cooker, Samsung climate control, EV charger. Situated within 2 miles radius - Chessington World of Adventure Resort, Painshill, RHS Wisley, Golf Courses, Restaurants, Supermarkets. 0.6miles to Oxshott train station and 30 mins to Central London. Both LHR and LGW are 21 miles away.

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.

River Thames near Windsor, Heathrow & London
Our home sits on the beautiful river Thames in Wraysbury near Windsor. The river runs past the end of the garden. There is a large west facing terrace, from the master bedroom. There is a large living room, kitchen and dinning room. 3 double bedrooms. There's parking for 2 cars in the garden. Windsor, Windsor castle and Lego land are about 20mins away my car. From Wraysbury station you can get into London Waterloo in 42mins. Heathrow is only 15mins drive away.

Beautiful 3 bed home with large driveway parking
Located close to Camberley town centre and a 5 minute drive to Frimley Park Hospital and local business parks. The house is a recently refurbished Victorian semi detached building. It has a character typical of its period and offers a warm and inviting clean space whilst retaining a homely atmosphere. There are a number of local parks within walking distance and a small high street at the end of the road which has a number of restaurants, takeaways and pubs.

Modern 1-Bed Self-Catering Home, Zone 6 London
Enjoy a stylish experience at this centrally-located home. This is a modern and tastefully designed self contained home, comes with a double bedroom with en-suite bathroom, fully equipped kitchen, utility room, garden and living-room with own driveway for free parking. 2 mins walk to West Ewell station from the property and it is only 35mins by train to London Waterloo It is I’deal for tourists, friends, business travellers or contractors

3 Bedroom Maisonette House in Kew Gardens/Richmond
Elegant and spacious 3-bedroom maisonette just moments from Kew Gardens. This light-filled home features a stylish living area, fully equipped kitchen, and a beautiful private terrace—ideal for outdoor dining. Located close to Kew Gardens Underground Station with fast links to central London. A perfect base for families, friends, or business travellers seeking comfort, charm, and convenience.

The Coach House, Halstead Hall
The Coach House, Halstead Hall is a cosy, detached cottage within the grounds of the Grade II listed residence of the esteemed author Edith Nesbitt. Located in the peaceful village of Halstead, this idyllic retreat offers tranquility while being conveniently just a 20-minute train journey from London, accessible via a short taxi or bus ride to the local train station.
Popular amenities for house rentals in Chessington
House rentals with a pool

Bright spacious home with natural swimming pond

Wellness Escape by River: Sauna, Pool, Hot Tub

The Old Granary

Modern Escape-Jacuzzi & Ice Bath

4 Bedroom Family Home nr Notting Hill w Garden

Luxury lodge with heated pool and tennis court use

Serene and private double ensuite near Forest Row

South Wing of Country House
Weekly house rentals

Beautiful 2 Bedroom Mews House

Detached 6 bedroom family house with Sky TV

Rural Retreat near Dorking

Spacious Family Bungalow with Garden for up to 7

Country home with amazing views

House near Epsom, ideal for business travelers

Charming Surrey Cottage, 30 Mins to Central London

15th-Century Thatched Cottage on 2.5 Acres
Private house rentals

Spacious, Garden home by Walton Station

A Cozy Home Away from Home

3 bedroom house with parking

Lovekush Epsom/Banstead 5 Bedrooms, London Views

A Gentle Riverside Charm 2 bedroom Mews House

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

Magnolia Lodge - 4 Beds, Fabulous Garden, Parking

Lovely 3 bedroom cottage with garden
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 $51 SGD per night before taxes and fees

Verified guest reviews
Over 310 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
- Paddington
- Big Ben
- British Museum
- Covent Garden
- London Bridge
- Marble Arch
- St Pancras International
- Hampstead Heath
- Buckingham Palace
- Tottenham Court Road
- Kings Cross
- The O2
- Natural History Museum
- Wembley Stadium
- Piccadilly Theatre
- Trafalgar Square
- ExCeL London
- Battersea Power Station (disused)
- Emirates Stadium
- Royal Albert Hall
- Olympia Events
- Russell Square
- Camden Market
- Borough Market




